Editor’s note: This interview was the first of two Affleck did with Playboy, originally published in the December 1999 issue of Playboy.

Ben Affleck, in jeans, T-shirt and sneakers, drives his pale blue 1970 Chevy Malibu convertible, a boat of a car, into a parking space on Beverly Boulevard in Los Angeles. He puts a couple of quarters into the meter and, while turning a few heads, walks into a restaurant called Red. He apologizes profusely for being late, even though it’s only 15 minutes. “I’m not one of those asshole actors who gets off on being late,” he says. Affleck orders iced tea. He’s a little embarrassed when the manager recognizes him and suggests moving from a table by the window to a more comfortable–and discreet–booth. The handsome 27-year-old millionaire whose life, it would seem, is now the stuff of male fantasy is still surprisingly modest, unguarded and at times wildly indiscreet.

Affleck smokes, drinks, works out, laughs a lot and clearly has a good time. Only a few years ago, as a struggling actor, he slept on sofas in friends’ apartments in Hollywood. Now, thanks to such hits as Good Will Hunting and Armageddon, he’s in the midst of renovating a six-bedroom 8000-square-foot Spanish-style villa in the Hollywood Hills, replete with fountains and pool. It cost him about $1.7 million. He also has a comfortable Tribeca loft in New York with an array of vintage video game machines.

Affleck earns about $6 million for a studio film now, and his appeal rests not only on his good looks and screen charm but also on his all-American boyishness and comedic talent. “Ben’s the real thing,” Jerry Bruckheimer, Armageddon’s producer, told Details. “He’s got that square jaw, that real Americana look, without being pretty. Women want to be with him and men want to be like him–which is what movie stars are made of.”

The veteran director John Frankenheimer, whose thriller Reindeer Games is set to be released this month, chose Affleck for the lead role as an ex-con who becomes involved in a plot to rob a casino. “I needed a vulnerable actor, a strong, masculine actor and a very good actor,” said Frankenheimer in the Los Angeles Times. “Ben is all those things.”

Another film with Affleck will be released in December. In Daddy and Them, a comedy directed by and starring Billy Bob Thornton, Affleck plays an attorney in Little Rock, Arkansas, who, with his lawyer wife (played by Jamie Lee Curtis), becomes entangled with an eccentric Southern family.

Affleck, who shares an Academy Award for the screenplay of Good Will Hunting with his friend Matt Damon (the two also starred in the film), is one of the busiest actors in town. His recent films include Kevin Smith’s controversial religious satire Dogma (which reteams Affleck with Damon), as well as a romantic drama, Bounce, opposite ex-girlfriend Gwyneth Paltrow, with whom he still has a friendly, if complicated, relationship. Affleck and Damon are also writing at least two projects and, through their company, Pearl Street Productions, are producing their first film, The Third Wheel, a comedy in which the two actors have supporting roles.

Affleck likes to say that he was once a gangly and awkward teenager who was shunned by girls. But now his name appears frequently in gossip columns and tabloids as a man-about-town. “I’ve been linked to Pamela Anderson, Calista Flockhart–and Matt Damon,” he joked to the Detroit News. But a longtime friend, French Stewart, who stars on the television series Third Rock From the Sun, told Details last year that women fall all over themselves when they meet Ben. “If they get within 50 feet of him, their pants will fly right off their bodies.” Affleck cringes and laughs at the comment.

Benjamin Geza Affleck (Geza is the name of a Hungarian family friend) was born on August 15, 1972 in Berkeley, California. One year later the family relocated to a middle-class neighborhood in Cambridge, Massachusetts. His mother, Chris, with whom Affleck is very close, is a schoolteacher. His father, Tim, worked with the prestigious Theater Company of Boston (which featured Dustin Hoffman, Robert Duvall and James Woods). He also worked at a series of blue-collar jobs including bartender and as a janitor at Harvard (the basis for Matt Damon’s role in Good Will Hunting).

Affleck says his father was an alcoholic, which led to the divorce of his parents when he was about 11. As the older of two kids (his brother, Casey, is also an actor), Ben remembers often playing the role of peacemaker. Tim Affleck became sober around 1990 and works at a recovery center for drug and alcohol abuse in Indio, California. Affleck says he speaks to his father periodically and has a good relationship with him.

At Cambridge, Ben grew up two blocks from Matt Damon, and the two were childhood friends. They played Little League together and were both students at the Cambridge Ridge and Latin School, where they took drama courses.

At the age of eight, Affleck got his first big break on the PBS television series The Voyage of the Mimi and then landed small parts in television series and commercials. His mother wasn’t enthusiastic about her son’s involvement in acting, partly because it seemed frivolous. She put the money he earned in a college trust fund. Yet Ben persisted.

After graduating from high school, Ben spent a semester at the University of Vermont in 1990, later switching to Occidental College in California in an effort to keep his mother happy. But Affleck dropped out of college and lived in a grungy Hollywood apartment. In 1992 he was cast together with Damon as anti-Semitic students in the drama School Ties, about a Waspy prep school in New England.

In 1993 he had a small role in the NBC series Against the Grain and landed his first significant part, in the Seventies retro movie Dazed and Confused. It didn’t help his career.

“After that film, I was probably the poorest I ever was,” Affleck told Premiere. Moreover, he was told by producers and studio executives that the baby fat on his face and his height (6’3″) made him an improbable leading man.

But to Affleck’s delight, he secured a lead role in Mark Pellington’s Going All the Way. The sweet-natured film failed, but it was one of the few times Affleck hadn’t played a bad guy.

In another failed film, Kevin Smith’s Mallrats, Affleck played a store manager. Smith wrote his next film, Chasing Amy, with Ben in mind for the lead role. The independent 1997 comedy-drama, in which Affleck plays a cartoonist who falls in love with a lesbian, was a hit at the Sundance Film Festival. Producers and studio executives took a second look at him.

Affleck owes a great deal to Smith. It was Smith who took the screenplay for Good Will Hunting to Harvey Weinstein, co-chairman of Miramax, who salvaged the project and purchased it for $1 million from Castle Rock. (Castle Rock owned the movie but clashed with Affleck and Damon over who should direct it and where it should be filmed.)

The 1997 film, directed by Gus Van Sant, was a sensation. It earned nine Academy Award nominations, and Oscars were given to Affleck and Damon for their screenplay and to Robin Williams for best supporting actor. Affleck and Damon became instant celebrities as well as stars.

Affleck, regarded for several years as an indie actor, was then offered a top role in the megabudget action film Armageddon. At the request of producer Jerry Bruckheimer and director Michael Bay, Affleck had his teeth capped and buffed himself up to play a wildcat oil driller who falls in love with Bruce Willis’ on-screen daughter, Liv Tyler, even as Ben, Bruce and several other tough guys save the world from a fiery collision with an asteroid. He earned $600,000 for the part.

“I just thought, I’m set for life,” he told Premiere last year. “Gone fishing. I’ve got my 600 bones, and I won’t have to do any more shitty movies that I don’t want to do.”

Affleck followed that film with Shakespeare in Love, 200 Cigarettes and a comedy, Forces of Nature.

We asked New York Times entertainment reporter Bernard Weinraub (who previously interviewed Clint Eastwood for Playboy) to meet with Affleck. Here is Weinraub’s report:”The first time I met Ben was at a Miramax party at the Sundance Film Festival in Park City, Utah. It was the year that Going All the Way was shown at the festival, and Affleck was practically unknown. He seemed to be the tallest guy in the room, and he was also one of the most engaging. When he heard that I had once covered politics he dropped all conversation about acting and wanted to talk about President Clinton (this was way before Monica) and his troubles with Congress. (Affleck is a serious Democrat.) He seemed not only smart but surprisingly well versed in politics.

“I saw him at Sundance last year under different circumstances. He was already a star. His name and picture had been in the tabloids with Gwyneth Paltrow. But he had flown into Sundance to see some films. At the Holiday Village Cinema, Affleck waited, just like all of us nonstars, to get into the overheated theater. He chatted with the crowd around him and bitched about the long line, just like everyone else.

“When we got together in Los Angeles, Affleck was funny, eager to please and seemed a little dazed at his success. Beneath his self-deprecating humor, though, he is shrewd about his career and acting choices and seems to know exactly where he’s heading. He’s also aware of his public persona. While we were seated outdoors at one restaurant–the air-conditioning inside set off his allergies–a Jeep suddenly stopped and three teenage girls climbed out, giggling and asking for his autograph.

“He smiled, signed the autographs and posed for a picture or two with each girl. They left happily. Affleck returned to his iced tea and grinned. ‘Who would have thought?’ he said.”

Playboy: It’s been two years since Good Will Hunting. How has success changed your life?

Affleck: There was a kind of hysteria, a publicity frenzy, that changed my life from total anonymity to going to shopping malls in Pittsburgh or South Dakota and hearing everybody say, “Hey, that’s that guy–he and his friend won the Academy Award.” And that was really overwhelming. I mean, a lot of people do it a little more gradually. Having the Oscars at the end of March and then Armageddon in July required a lot of adjustment. Someone told me Madonna said, “People are basically worthless the first year after they become famous.” I think that’s something both Matt and I felt, which was a complete sense of bewilderment and being in a daze. Imagine having to renegotiate your relationship with the entire world.

Playboy: Does that mean your relationships with women as well? How have they changed?

Affleck: It wasn’t like this before and I’m not stupid enough to think that it’s me. I remember when I first got on the TV series Against the Grain back in 1993. All of a sudden I hooked up with three hot women in a month and I couldn’t believe it. I was telling my friends, “Man I’m on the hottest fucking streak right now. I don’t know what it is. I’m on fire.”

They were like, “Do you think it has something to do with the fact that you’re on TV?”

It had never occurred to me until then—and I never forgot it after that. Kevin Bacon once said, “Anybody can get laid when they’re famous. The champion thing is to get laid when you’re not famous. That’s what’s really hard.” Boy, does that turn out to be true.

Playboy: Have you figured out why being famous helps?

Affleck: Women can be attracted to things other than men, which has to do with power, money, status, that provider kind of thing. Being a successful actor represents those things. You can be seriously disfigured or whatever and women will still be attracted to you. And that’s a change for me. Women were never that way with me. Teenage girls didn’t used to shriek when I walked into a room. I was lucky if I could get a phone number. Part of it’s just the power of being on the screen. And now there’s something that’s less appealing about it.

Playboy: Something less appealing?

Affleck: I was in a casino a month ago, at the Hard Rock Cafe’s casino expansion. And I was sitting at a table playing blackjack with a couple of buddies of mine from high school. And we were sitting there, bullshitting and drinking, playing cards. And this girl, very attractive blonde woman, probably about 25, a little drunk, walked over to me and goes, “How would you like it if I sucked your cock until your eyes came out?”

I was taken aback and I was kind of like, Wait a minute. OK, she was a little bombed. That was just her line. That was her approach. I don’t know this lady from anybody else. Maybe she’s mentally ill, but every now and then people say things like that. Another one was, “I really want you to go down on me. That’s all I want in life.” All of a sudden there’s something that makes you kind of go, “Ah, this is weird and not that appealing.”

My friends said, “What are you doing? Go to the room, now.” They were really, really disappointed in me. But there’s something about it that kind of kills the magic. It’s just not that appealing. And I bet you that most people are like me. Not that I’ve lost my sex drive. There’s just a difference between the fantasy and when it really happens. Anyway, I’m not a one-night-stand kind of guy. To me, sex is much, much better and much more interesting and satisfying when it’s got a psychological element to it. When I don’t know the person, I tend not to be that into it.

Playboy: When you date, it tends to make news. How does that feel?

Affleck: One of the weirdest things in my life was the time I had fallen asleep on my couch watching television and was dreaming about this relationship I had with this woman. When I woke up I was watching CNN and there was this story about me and this woman. On CNN. I thought, This is madness. It felt sort of weird, like I was living somebody else’s life.

Playboy: Would the woman have been Gwyneth Paltrow?

Affleck: Yeah.

Playboy: How is a relationship with a movie star different from one with somebody unknown?

Affleck: It gets more attention from the paparazzi. It gets more attention from the tabloids, which is definitely more difficult. I’ve only really had one relationship with a movie star, but I found that person to be so bright and mature and sort of together that I didn’t find it difficult at all.

Playboy: So the difficulties come from the paparazzi and the tabloids?

Affleck: Most intelligent people understand tabloids to be about 80 percent false. But some people read them and call my mom and ask, “Is this true?” And then my mom calls me and says, “Are you married?” And I say, “Mom, if I were married, don’t you think I would have called you? Are we on the outs? I mean, don’t you think you might have been there?”

Playboy: That really happened?

Affleck: That actually happened to my mother. They said that I had married Gwyneth. Or they’ll say you’re sleeping with any number of different people when there’s no truth to it, or they will say something that casts you or somebody you care about in a negative light. I mean, look, it’s part of the deal. I totally understand that. I accept that they’re there. It’s really just a small ongoing battle between a few tabloid publishers and a few celebrities and nobody else gives a fuck except to flip through them in the supermarket line. So it’s not like some great epidemic. I just don’t care for them all that much.

Playboy: The tabloids seem to be fascinated that you’ve remained friends with Gwyneth.

Affleck: Yeah. We’re about to work together, on Bounce. It’s directed by Don Roos, who did The Opposite of Sex.

Playboy: Is it going to be strange working with her?

Affleck: No. We talked about it. I’m just finally arriving at the point where I’m mature enough to be friends with somebody I’ve had a relationship with. And this is really the first time. Luckily it happens to coincide with a very public relationship. So that’s fortuitous. But it’s a combination of her being really great, us getting along really well and both of us wanting it to be this way. We broke up, decided we were better if we weren’t a romantic couple. But we never had enough acrimony toward each other to override the fact that we care about each other and enjoy each other’s company.

Playboy: Are other former girlfriends generally pissed off at you?

Affleck: Mostly, yeah.

Playboy: Why?

Affleck: Probably justifiably so. If I were the next guy to go out with them I’m sure I would be nodding in agreement about what an asshole their ex-boyfriend was. It’s not like I was a womanizer or physically abusive or psychologically abusive or whatever. It’s just that these relationships never end well. I think what happens is, I end up wanting to be out of the relationship. During the course of a relationship, if you get dissatisfied and unhappy and don’t say something, if you don’t deal with it right then, it just festers and stays there. So instead of saying, “Look, don’t do that, please don’t act this way,” I go along with it until I just don’t want to be in the relationship at all. Then I create some incident or do something or just don’t call. And then she’s pissed. And I can’t necessarily blame her at that point since I’ve developed such a passive-aggressive rage that I have no sympathy and tell her, “Well of course I didn’t call you. If you weren’t such a nagging, shrewish harpy I’d call you.” But that hopefully is something I’m growing out of.

Playboy: And why are things different with Gwyneth?

Affleck: I see her, we hang out when we’re in the same town or whatever. And I really think she’s a phenomenal actress and in that sense there isn’t anybody I’d rather play opposite than her. I don’t know, maybe it’ll be weird making the movie with her. I don’t think so. What I think will happen is she’ll end up causing me to work three times as hard as I would have. And that’s something I keep wanting to do, maybe because I feel like my work is better when I’m really pushed.

Playboy: Do you mean you have to keep up with Gwyneth?

Affleck: More than anyone else, she knows if I’m faking a scene or walking through it. She’s not only really talented but she’s incredibly perceptive. I think it’s what makes her a really good actress. Gwyneth has this almost scary capacity for being able to see into people in a nonjudgmental way. Plus I have to work hard just to stay up to her level of work, which she seems to do almost effortlessly.

Playboy: When you started getting a lot of press attention, you earned a reputation for saying some wild things. How did that affect you?

Affleck: I made a lot of mistakes and did a lot of stupid things and ended up probably being a little bit more conservative than I used to be–the way I deal with people. You are accustomed to being able to say whatever you want, voice whatever opinion you want and nobody really cares all that much. Your friends sort of know you, and that’s about it. All of a sudden you feel like getting into a bunker.

Playboy: Was there ever a time when you thought that success might be going to your head?

Affleck: First of all, you just have to be careful. You have to remember the standards of the real world. I caught myself being impatient about something that I had no business being impatient about or feeling irritable about. “I don’t want that sparkling water!” or “I can’t believe this is an old limo.” Then you just think, What kind of an asshole am I? My feeling is that people who are complete assholes were like that before.

Playboy: What happens now when you go to the supermarket? Or the movies?

Affleck: Sometimes people don’t recognize me and sometimes they do, and in some instances it can turn into a real nightmare.

Playboy: Care to explain that?

Affleck: Look, it feels bad to be the kind of person who says, “Please leave me alone, I’m trying to watch a movie.” But, by the same token, people sometimes just come up to you in the middle of a movie. You go to the Cineplex and you buy your ticket and you think, OK, I’m here and I’m just going to watch the movie. Then slowly people will cluster by the exits, then come over and say, “Would you sign this real quick?” And you’re like, “Hey, I’m in the middle of the movie.”

Playboy: Is money an issue with you and your friends and family? With the exception of Matt Damon, you’re earning much more money than they are.

Affleck: It’s a strange thing. I don’t know if my dad ever made more than $30,000 in a year. If he did, I didn’t see any of it. But he was a carpenter and an auto mechanic and then a janitor at Harvard, and my mother was a public school teacher with a capped salary of $45,000 a year. So we were somewhere around middle class. And it’s kind of weird. I mean, it’s satisfying. I give money to my mom, and I’m going to buy her a house, and that kind of stuff feels really good. And I’m pretty generous. If people need a loan here and there, I’m perfectly happy to help out because I understand my good fortune. But I also am cautious about letting myself get taken advantage of. Most of my friends are pretty cool about the money. Most of them, if they borrow money, are really conscious of paying it back. I think they’re self-conscious about feeling like suckweeds or whatever. So it’s not as much of an issue as I would have thought. You know, whatever that number is on your ATM receipt, it can separate people.

Playboy: That’s quite different from your financial situation when you first came to Los Angeles.

Affleck: When I got to LA, my family had me go to dinner with this guy who had been acting here for 20 years. He gave me this big lecture and said, “You know how much money I made in 20 years of acting? Eight thousand dollars. And I’m a carpenter.” He was just really unhappy and it was depressing. Then he got really stoned and I went home and felt sick. I think it was just morbid fear. I was 18. That fear stays with you so intensely and you’re constantly just getting turned down for what you think of as the most vapid, stupid kind of paycheck, Baywatch things, and you think, Jesus, if I’m not good enough for this then I’m not going to make it. This town is too hard, and people were always telling me, “You’re too big, you’re too tall, you can only play bullies and you will never be a leading man.

Playboy: They said you were too tall?

Affleck: Too tall, 6’3″. All the actors are like 5’10” or 5’6″. Or you’d be an extra for money and then get shit on by the crew, who tells you, “Stay away from the table, you can’t have any of that food. That’s real people’s food.” The extras have their separate food table. It’s subhuman the way you get treated.

Playboy: Welcome to LA.

Affleck: I came to LA and looked on my map and it was like, “Well, what’s Hollywood?” Drove there, and got an apartment where more crack was sold in half an hour than I’d ever seen in my entire life. I realized that Hollywood was the Times Square of LA.

Playboy: Were you able to get work?

Affleck: I did a Danielle Steel TV movie with Patrick Duffy and Lynda Carter and I was all psyched—it was with Wonder Woman, you know what I mean? All my friends would ask me about her tits. Well the tits, they’re big, right? She’s got nice tits? I said, “Yeah, yeah. They’re pretty nice.” So I was happening, because I had seen Lynda Carter’s tits in real life. And then I got cast in School Ties, but I had a real shitty role. It really sucked.

Playboy: Wasn’t Matt Damon in that movie, too?

Affleck: Yeah, and Matt had a better part. He was the main bad guy. I was like the junior bad guy. But at least he was three-dimensional anti-Semitic, whereas I was paper-thin anti-Semitic.

Playboy: Describe how you lived back then.

Affleck: I lived all over the place. I lived in Hollywood, then I moved. Matt and I got money from School Ties and we blew it all in a couple of months. We made $35,000 or $40,000 each and thought we were rich. And we were shocked later on to find out how much we owed in taxes. We were appalled: $15,000! What? But we rented this house on the beach in Venice and 800 people came and stayed with us and got drunk. Then we ran out of money and had to get an apartment. It was like everything was exciting. So we lived in Glendale and Eagle Rock and we lived in Hollywood, West Hollywood, Venice, by the Hollywood Bowl, all over the place. We’d get thrown out of some places or we’d have to upgrade or downgrade depending on who had money.

Playboy: Where are you living now?

Affleck: Near the Hollywood Bowl. It’s a really great place. I rented a house there first. Matt and I and a couple other guys we went to high school with rented a place up there when we sold the script for Good Will Hunting. I really liked it. LA is kind of zip code snobby. Anything east of La Brea is going to be less expensive. For no real reason, you know what I mean? So I got a pretty cool place. Needs some work. And it feels like that Tom Hanks movie The Money Pit. I am so living in the money pit. Guys come at five in the morning and start working.

Playboy: There are some great old houses up there.

Affleck: There are two great things about looking for a house in LA. One, every house has some elaborate history—Buster Keaton once slept with three women in the attic. Second is that they are currently being lived in by people who you know, or people you’ve heard of. When I was looking, every time I went to an open house I would try to sneak around and look at what awards or scripts or movie posters there were, so I could figure out, OK, this must be so-and-so’s house. It was great.

Playboy: What about your romantic life. Are you seeing anybody now?

Affleck: Nope. One hundred percent single.

Playboy: Are you on guard when it comes to women?

Affleck: I’m not too guarded. What’s fun for me is flirting and having a good time–that’s really fun. But a lot of times it’s much more fun than all the bullshit, the responsibilities and compromises that go along with sustaining a relationship that I hardly have enough energy for at the end of the day. But I like flirting and meeting somebody and saying hi and letting it happen. In this day and age, as soon as you sleep with somebody it conjures up this whole set of issues and you’ve created this whole thing. There’s this responsibility. It’s almost more appealing to just be flirtatious and have a good time. Then you can flirt with as many people as you want and it’s fun, it’s relaxing and you’re not a bad guy and you’re not doing something wrong. Maybe I’ll look back at this time in my life in ten years or 50 years and say, “God, I really should have capitalized.” I’m certainly no monk, but it just seems a little skeezy to me to do that. But you’ve got to have fun in life.

Playboy: How many serious relationships have you had?

Affleck: Serious, serious relationships, heavy-duty relationships? Four or five. I qualify those as relationships that last a year or more. I started when I was 14. She was a little older. I was a freshman in high school, she was a senior. When you’re 16 you can fall in love every ten minutes, but these were people I really cared about and still care about.

Playboy: What happened in terms of meeting women when you got out here to Hollywood?

Affleck: I got shot down pretty regularly, but I didn’t mind. There’s some honor in taking a shot, going down swinging. So I guess in that respect I’ve been confident, but not in the sense that I assume women will like me.

Playboy: Have you been burned much by women?

Affleck: Yeah. I’ve had my heart broken a couple of times. There was a heavy heartbreak when I was 13 or 14, and then I had a pretty traumatic experience breaking up with this woman I’d gone out with for a long time when I was in my early 20s. This woman cheated on me and I found out. I got upset and confronted her and didn’t really want to break up. It’s that really humiliating thing where even though you feel like you’ve been wronged, you’re still so in love. What’s really painful is that you don’t even want to end it, even though you know you should. Of course, eventually I did and we broke up and I got over it, but it was kind of scarring.

I’ve probably been pretty lucky, I haven’t been burned too badly. Like I said, my past two major relationships have ended amicably and I’m really good friends with the women still, and that’s a nice thing. So I think I’m on the right track.

Playboy: What has been your biggest disappointment with women?

Affleck: One of my biggest disappointments was Viagra. I figured it’s this old-guy drug, if you can’t get a hard-on you take Viagra. But then these guys start telling me, “No, no, no, you can take it too, and it’s like you were 14 and jerking off six times a day.” So somebody gave it to me. I took half and felt like I almost had a heart attack. I had to sit down and all it did was make me sweat and feel dizzy. And really unnerved. I felt no sexual effects whatsoever. So maybe I’m immune to Viagra. That was a huge disappointment for me. I thought I’d be able to recapture those days when I was 15.

Playboy: Have you ever thought of getting married?

Affleck: I’m starting to get to the age where you can feel that shifting of awareness. All my friends, men and women, but particularly women—there’s something that comes over them and it’s almost palpable. I think it happens earlier in women, starts to happen around my age—I’m 27. I don’t know when it happens with men. A little later. They will go along with it and get married. But usually it’s because of the women–they love babies, they start looking at wedding books, going to their friends’ weddings and talking about who’s gotten engaged.

Playboy: Does marriage scare you?

Affleck: I try to be very up-front. I’m not in a consistent enough place where I can say, “Well, here are my ground rules for relationships,” because they are in flux. They’re changing and I’m changing. One of the reasons I’m not in a relationship right now is that I just know at some level that I don’t want to be married, I don’t want to have kids. I’m just not ready for that. Everybody tells me not to get married. Every single person I talk to who’s over the age of 40, they give me this look like–and it’s unsolicited, too. They’ll just say, “By the way, wait, just wait. At least till you’re 40. The only reason to do it is if you want kids.” That’s what everybody tells me. The most grim view of marriage is from the entertainment business.

Playboy: What do they say?

Affleck: Oh, everyone has a story. Guys’ wives running around on them, taking their money. Peter O’Toole told me I should find a woman I hate, give her my house and skip the rest of it.

Playboy: You were about 11 when your parents split up. What effect did that have on you?

Affleck: I probably haven’t been through enough analysis to answer that question. I don’t know. I had to be the man of the house. I had to take more responsibility at an earlier age. I think it left me kind of schizophrenic—I never knew if I was young or old. I can be serious and heavy and feel very burdened and adult. Alternately, I can be very juvenile. I had a pretty good childhood. It wasn’t like we had a lot of money, but we weren’t poor.

Playboy: Your father worked several jobs, didn’t he?

Affleck: My dad was sort of a jack-of-all-trades. He was an auto mechanic for many years, an electrician, did some kind of construction stuff and then was a bartender and a janitor at Harvard. He left and went into alcohol recovery around 1990 at a really interesting place called the ABC Club in Indio, California. I think Indio’s chiefly famous for being the place where Jimmy Swaggart got caught with a prostitute. My dad went through recovery at this place and ended up getting a job there. He sobered up and I was able to reestablish a relationship with him and become friends with him, which is really a nice thing.

Playboy: Your father was a stage director, too.

Affleck: He was once a director or stage manager of a theater in Boston and worked with a bunch of people who are famous now: Dustin Hoffman, Robert Duvall, Jon Voight and James Woods.

Playboy: What sort of man is your dad?

Affleck: My father had an extremely difficult life. A lot of stuff in Good Will Hunting was inspired by things that I came to know about the world through my father. And Matt knows my dad real well.

Playboy: So the characters in Good Will Hunting were based on your dad?

Affleck: The character that Matt played has a lot more in common with other people, older people we know. People who are working class but who we think are really bright. That’s one of the inspirations–when you’re young and you’re looking at people and you’re trying to figure out the hierarchy of the world, who’s smart and who’s in which position, and then you start to recognize that there are a lot of really smart, capable people who aren’t afforded a lot of respect or position by the societal hierarchy. And so then it was about trying to reconcile that with the academic side of the world.

Playboy: Weren’t you surrounded by a lot of upper-class kids who went to Harvard?

Affleck: Yeah. I didn’t know quite where I fit because I wasn’t a fifth-generation Irish cop. My mother went to Radcliffe but then was a teacher and a product of that. I used to ask her, “Why don’t you get a job that pays some money instead of being the idealistic Sixties person who teaches in public school?” But there was something about going to the public schools in Cambridge, we were like the town kids. There were the real townie kids and there were these university kids at MIT and Harvard. It was weird when Matt got into Harvard and was able to see both sides of it. I would go hang out with him there and we had all these prejudices about these fucking Harvard kids. Then I kind of got to know a lot of them and they were really interesting, kind of cool people. There were some dicks and some stereotypical elitist assholes. But more often I found some pretty neat people there.

Playboy: Are you friendly with your father now?

Affleck: From about 13 to about 18, I didn’t really have a lot to do with my dad. Or see him very much. Then he went through recovery, and I moved out to LA. I was a long way from home and it was like I had just thrown my shit in the car and decided, Fuck college, this is what I want to do, I’m not going to waste my time, I want to go strike out and pursue my dreams. I came out here and my dad was a couple hours away, so I would go out and visit him frequently. It was nice. We’d spend long afternoons together. It was 110 degrees out in the desert in this quiet old town, inhabited almost entirely by Mexican Americans and Mexican nationals. And it’s a place that hasn’t really been built up much since the Fifties so it sort of looks like the Fifties. Except for the cars, it’s a quiet place, real hot, but kind of therapeutic. I think it was really good for my dad to be out there. We would go out and talk all day, and over the years I reestablished a relationship with him. And it’s now pretty solid.

Playboy: What led you to acting?

Affleck: I guess I was outgoing, precocious and obnoxious, like any child actor. You know–these kids with unbearably big smiles, and they’re four and wearing little fucking cutesy suits. Luckily my mother always hated the idea of my being an actor. Her best friend from college was a casting director in Boston who made an independent movie and needed a seven-year-old kid. So I did that. I barely knew what I was doing. It was like, “Go over there and come back here.” I guess I took to it and had fun. Then there was a casting call for a public television series that was coming through town. I was eight years old and ended up getting that. I did that one show, but every two years I’d go off for a month and a half or longer and shoot this kids’ drama show called The Voyage of the Mimi. The Mimi was a boat. They still inflict this thing on sixth graders in science classes all over the country.

Playboy: It was on PBS?

Affleck: Yes. I was 13 or 14 when I finished my last Mimi assignment, and by that point I really liked acting, liked being out there and being in the adult world and working and pretending and having fun. They gave me ten bucks a day, which was like a fortune to me. I bought comic books with that money. I had to maintain the lifestyle.

Playboy: Was there a breakthrough role?

Affleck: It’s hard to say. I did Dazed and Confused, but that was considered a bomb when it came out. It later became a cult college movie. I was the bad guy in that. I got sick of playing bad guys. But I really liked this guy, Kevin Smith, who’d done Clerks, so I went in to audition for Mallrats. That was a break in a lot of ways, though I didn’t realize it at the time. Kevin and I became friends; he decided to write Chasing Amy for me. I never auditioned or anything—he just cast me, which was a huge break. While we were shooting Chasing Amy, me and Matt were also working on Good Will Hunting.

Playboy: Kevin Smith seems to have been an important force in your life. He cast you in Mallrats, Chasing Amy and now Dogma.

Affleck: I started to get some parts, but I was the bad guy in almost every other fucking thing. Kevin called me one day, and it seemed too good to be true. He said, “I’m writing this movie about a guy who falls in love with a lesbian and I want you to play the lead. I think there’s a side of you that people really haven’t seen. You can really be a leading man and do some romantic things, and I don’t think you’re too big.” That was the running joke because there was a producer who told Kevin not to hire me because I was too big.

Playboy: What appealed to you about Dogma? Was it the controversy? Some people view it as anti-Catholic.

Affleck: I actually read it a couple of years ago, when I was making Chasing Amy. During the rehearsals he gave me the script as a kind of “Oh, hey, look what else I wrote. I’d like to make this down the road.” I read it and thought it was the most unusual, original, interesting script I’d ever read. In a world of homogenized movie products, where it’s just Die Hard this or Die Hard that and where everything has to fit into a mold, here was a movie that was completely fresh. And whether you loved it or hated it, you hadn’t seen anything like it. That’s what got me into it. I wanted to do it badly, so much so that I kind of secretly looked at the entire process of Chasing Amy as a two-month audition for this movie. He didn’t ask me to do it until we wrapped Chasing Amy, so I guess in some ways I was right.

Playboy: Are you surprised at the controversy? Disney, which owns Miramax, said the film was “inappropriate.” Miramax had to go elsewhere to release it.

Affleck: I think Disney was nervous about it because Disney has had problems in the past with certain groups. The issue of same-sex health care benefits really irked a radical and vocal fringe element of the religious right. There’s this sense that Disney is a liberal entity. It’s a vague and nebulous idea, and I think it irks the religious right that Disney puts itself forth as a family company when really, by God, it endorses homosexuality, among other awful things.

Playboy: How did you make Good Will Hunting?

Affleck: It was kind of embarrassing. Everyone is an actor with a script, and you feel like just another asshole with a screenplay. So we banged it out in two months one summer. We wrote the vast majority of that script in LA.

Playboy: When you sold it, the deal was that you had to be in it. And it all happened almost overnight.

Affleck: It was like a fairy tale that started over the course of a week. There was a bidding war. We got $600,000 to split, which was more money than either one of us had ever seen in our lives. It was like winning a lottery: $300,000! Jesus Christ! Can you imagine? I had just broken up with another girlfriend, which is why everyone says I was homeless. I had moved out of this girl’s house. She hates me now, by the way. I moved back in with Matt and another friend and I was staying on the couch and I said, “I’ll find an apartment. Whatever.” They didn’t really care. And it was easier to write over there. I didn’t have an apartment of my own, but all of a sudden I had $300,000—or $130,000 after taxes and an agent. But I liked to think that I had $300,000. And fuck if it wasn’t about the most incredible experience in the world.

Playboy: But then Castle Rock, which bought the film, wanted to revise it.

Affleck: Castle Rock didn’t want to revise; they were ready to make it. This is kind of a sensitive area and I don’t mean to bash them, but they had somebody who they wanted to direct the movie and it was a disagreement over that. We wanted to offer it to other people first, our dream people. I don’t know how to say this without sounding like a fucking cheap laminated poster in some sixth grade guidance counselor’s office, but we didn’t want to accept anything less than exactly what we wanted. We had ten directors in mind, the great directors. We wanted Gus Van Sant or Martin Scorsese and we felt like the material was pretty directable. We wanted to at least have these guys read the script–at least send it to them, offer it to them. Castle Rock wasn’t willing to show it to anybody else. They had their one person they wanted to make it with, and that was it. It was unusual, but they were true to their word and said, “If we ever have a creative disagreement with you guys, we’ll give you the script back.” And so they did. They said, “If you guys don’t want to do it this way, you’ll have to find someone else who’ll buy it back from us.” Which we did.

Playboy: You were making Chasing Amy at that time?

Affleck: Right. Well, we had sold our script a year and a half before that, but by the time we sold it to Miramax I was rehearsing Chasing Amy. And then no one wanted to buy it. Everybody in New York and Los Angeles got that script and every single person, everybody who was in the business of making movies, turned it down. Every single person. Harvey Weinstein and his brother, Bob, were the only people who wanted it.

Playboy: Why?

Affleck: We weren’t cool. We weren’t anything but two upstarts who got overpaid for a screenplay in the first place and had the audacity to think we could act in it too, when it was well known that we could probably get Johnny Depp or Brad Pitt or somebody like that to do it. Studios said they didn’t want to do it because we were encumbering the movie. That’s what we were told over and over again. And then we said we wanted to make it for $6 million or $7 million, $15 million tops. The people at Fox said, “We don’t make movies at that budget. We don’t make those kinds of movies.” Why don’t they fucking do those movies? Since it only cost $15 million and grossed $200 million, seems like those are the movies to do.

Playboy: The fact that you got Robin Williams helped.

Affleck: It became easier for everyone to believe in it once he signed on. It became a Robin Williams movie, so it didn’t matter who we were or who anyone else was. Robin is possibly the most commercial actor in the world. To his credit, he cut his price—Robin made a deal where he would only profit in the success of the movie. He believed in the movie, he showed up and worked incredibly hard in rehearsals. I thought that was rare then, and I realize it now even more. Robin Williams worked harder on that movie than anyone I’ve ever seen.

Playboy: Shortly thereafter, you got the part in Armageddon and worked side by side with Bruce Willis. It was the first time you held your own with a big star.

Affleck: It was an education. I mean, Bruce ended up being really nice to me, but he could have made my life hell on that movie. I wasn’t accustomed to the idea of a power struggle on a movie. There’s a kind of alpha dog thing that goes on between the studio, the director and the star. And this kid shows up who no one knows. Well, is this kid the real thing? There was a certain amount of tension, which I didn’t understand. Later I figured out it was all the interested parties trying to figure out who was going to end up running the show. Michael Bay [the director] is headstrong. Bruce is headstrong. I was cooperative and amiable, but proud. I didn’t want to be told to go fuck myself and sit in the corner. As long as no one was going to tread on me I was going to be perfectly amiable. Then you had the whole Dirty Dozen thing with a bunch of other guys in the movie. So that added to the testosterone. Everybody was sniffing around. I ended up getting along with Michael and Bruce, and I still talk to Bruce. He turned out to be just a normal guy.

Playboy: After Armageddon, you took a small part in Shakespeare in Love, when you could certainly have taken a big-bucks, high-profile part in another studio film. Why?

Affleck: Everybody told me to pass on that. Michael Bay said, “Don’t do some Shakespeare movie in tights.” People said, “It’s not a lead. You’re doing somebody else’s movie, and this is like some art movie, and you got to build a career as a leading man, and you’re coming off Armageddon and on and on. And besides Gwyneth, there are a bunch of British actors in it, and nobody has heard of Joseph Fiennes.” But I loved it. I saw Joe’s screen test and thought that he was (continued on page 204)Ben Affleck(continued from page 80) tremendous. I loved the script and I loved all those actors, like Judi Dench, and it was intimidating. I thought, At least I’ll get the chance to prove to people that I can do this. A lot of people could have done Armageddon, but this was a stretch. I was going to do a British accent. And to be in the company of some of those extraordinary actors and not be completely wiped off the screen was what I wanted. I am so glad I did it. People cautioned me about doing Dogma, and I’m glad I did that one, too.

Playboy: What sort of parts are you offered now?

Affleck: There’s no shortage of parts for a leading man between 25 and 35; probably 80 percent of the movies are written with that guy as the protagonist. So I get comedies and action-adventure movies, superhero movies, weird independent movies, bad independent movies, good independent movies. I even get scripts where the lead is a Black woman, but, “We can change it and rewrite it if you’re interested.”

Playboy: With your career going so well, do you appreciate what’s happening to you?

Affleck: I don’t think I have appreciated enough the good fortune I’ve enjoyed. I get the opportunity to do incredible things and sometimes I just feel numb. I’ll be with my friends, and they’re pointing to a woman and saying, “She’s really beautiful and she’s looking at you and she wants to come over here.” And there are times I just don’t have the interest or the energy to pursue all those things, be it women or the opportunity to travel somewhere or meet someone. Sometimes I just want to stay at home. Then I think, This is going to go away and I’m just going to be sitting on my porch and I might wish I’d enjoyed it more. But you can’t make yourself do that. I don’t know why.

When I was 16 I got my own money and bought a four-door 1977 Toyota Corona station wagon. It leaked, it was a shitbox. This was in Boston, so when water would collect on the floorboards it would freeze, so there was ice in the car. It just sucked. But I had a car and I got around. I was always so envious of the guys with the Lexus and Mercedes and the big SUV. They’re always middle-aged guys. I said, “This is wasted on this guy, this is unfair, he doesn’t appreciate this car and I would really, really appreciate it.” So in a weird way I feel like I’m that guy. I feel like fame is almost wasted on me. I already don’t want to have sex five times a day. It’s kind of depressing.

Playboy: Are you writing another screenplay with Matt?

Affleck: Well, the trick now is that we’re writing two movies at once. So whichever one turns out better will be the one we turn in first. We also happen to have been paid by two separate movie studios to write something. Not much money, by modern screenplay standards. But we’ve cashed the checks anyway, so we owe scripts. We’ve put off doing them because both of us, I think, wanted some time between Good Will and our next movie. We were sick of hearing about ourselves. And I assume everyone else was sick of hearing about us.

Playboy: Are there strains in your friendship with Matt?

Affleck: Matt and I have strains in our relationship the way I have strains with the rest of the friends I’ve known my whole life. I mean, Matt’s a fucking slob and he won’t clean and he can be annoying. He comes over and he leaves his shit around and I say, “I’m not your fucking maid, pick up your dishes.” It’s the same way my friend Aaron will leave the newspaper all over the bathroom floor of my house, no matter how many times I say, “Don’t do that.” But actually, with Matt, it’s probably helped to have somebody who is going through the same experiences. We were always around each other. We’re probably better friends now. We’re able to bounce stuff off each other. I think we value our friendship more and understand how rare it is to have a good friend. There’s a small group of guys I’ve known since I was a kid. I value all those guys more. Obviously Matt in particular, because we have a common experience. We can say, “You know how weird this is?”

Playboy: How competitive are you with Matt?

Affleck: It’s always been an issue, ever since we were teenagers. Always, every single movie. So that’s something we came to terms with a long time ago. Same with my brother, who’s an actor and is working a lot now. I think the way that we’ve dealt with it successfully is to be really straight up about it. We’re both auditioning, we both want to get the part, we both want to do well. But we both feel, If it’s not me, I’d rather have it be Matt than somebody else. I think that’s the secret to a good friendship—you always root for the other person and support the other person, whether it is Matt or my brother or whoever. If you have a good friendship with somebody, you enjoy his success. You know you’re not good friends with somebody if his success pisses you off. Sure, there have been times when I’ve gotten something and Matt hasn’t or Matt’s gotten some part that I haven’t, but it’s never been difficult and we’ve never been exclusionary about it. It’s interesting to share experiences, and even if my career totally falls apart or I have one of these tragic PR disaster things—get arrested with a male hooker or something—or if I just do 15 shitty movies and no one wants to hire me again, I still really hope Matt does well. I wouldn’t associate my failing with his success. We’ve always helped one another. My brother gave Gus Van Sant the script for Good Will Hunting, because he got to know Gus by doing To Die For, which Matt auditioned for. They said, “You’re too old.” And he said, “You’ve got to hire Casey Affleck, he’s brilliant.” It’s always been that kind of thing. Frankly, I’m uncomfortable if my friends aren’t doing well. I feel like I have to do something to help them out. We’ll sit around and talk like, “We got to do something about so-and-so. He’s not working and he’s unhappy, let’s think of something.”

Playboy: Do you ever get tired of talking about your friendship with Matt?

Affleck: I understand the questions. Ben Affleck and Matt Damon, they’re friends, they’re pals, they grew up together, isn’t it great and cute? I get all kinds of questions, like, “So how’s Matt?” or “What’s Matt like?” And I don’t know what sort of answers are expected.

Instead of saying Matt’s fine and he’s doing his thing, I’ll be like, “Well, let me tell you about Matt. Matt can give a blow job in a way that’s incredible, really special.” Most of the time it’s like Entertainment Tonight, and they can’t air it. But then sometimes you think you’re safe, but sometime writes it down and it ends up being taken out of context in Out magazine.

Playboy: Does Matt ever get pissed off about that?

Affleck: Matt gets it. We have a similar sense of humor, which I think is the main reason we’re compatible as friends and in terms of writing. He always thinks it’s funny. It’s just a question of the rest of them.

Playboy: Let’s see if you’ve learned your lesson: What is Matt Damon really like?

Affleck: [Laughs] He gives a really great blow job.

Most people are like me. Not that I’ve lost my sex drive. There’s just a difference between the fantasy and when it really happens.