20 Questions: Garry Shandling
July, 1987
Those lips! That hair! And a sense of humor, too. Garry Shandling, though well known for his relationship-oriented comic routines and for guest-hosting "The Tonight Show," has recently resurrected the Burns-and-Allen style with great fanfare. And success. "It's Garry Shandling's Show," on Showtime, has just been renewed for three years. Contributing Editor David Rensin spoke with him between script meetings at the comedian's Los Angeles office. Said Rensin later, "While interviewing Shandling, I realized that I had seen him three weeks before in a restaurant, dining with four very attractive women. At the time, I figured he had to be David Brenner."
1.
[Q] Playboy: On stage, your tales of dating woes seem so genuine we suspect the private Garry Shandling is not much different. Is it you or is it a character?
[A] Shandling: My "character" is an exaggeration. I am basically a single guy who is as normal as you--which is frightening. When I host The Tonight Show, for example, that's Garry. If I look at a video tape and see myself being fake, I get very pissed. Work should be an extension of expressing who you are. Some people need their work to give them an identity. I don't. The act is a little more intense than my real life, because the funniest parts of being single are those lonely, painful moments. The great dates and great relationships aren't funny. So I talk about the bad ones and people assume that I have a horrible dating life--which is, unfortunately, true.
2.
[Q] Playboy: Who usually breaks up with whom?
[A] Shandling: In my early 20s, it was always the woman, which is why I was insecure then. As I grew older, it became half and half. Now I bail out the second I know a woman's gonna dump me.
3.
[Q] Playboy: Have you ever found the ideal woman?
[A] Shandling: I've never been gripped with that feeling that this is the one--even when it comes to a pet. I had to go to The Humane Society once to pick out a dog, and I had to go back three times before I found the dog I wanted.
4.
[Q] Playboy: What if you found Miss Wonderful and got married? Would the act suffer?
[A] Shandling: No, because I would feel just as awkward about marriage and be just as confused about how to handle it. Mostly, I'm confused about women, but I'm also confused about lots of other things in life. I can apply the confusion to anything.
5.
[Q] Playboy: What confuses you about women?
[A] Shandling: Like anybody else in a bad relationship or on a bad date, I wonder how the other person can actually be like that. Friends of mine say, "Well, how can you go out with somebody like that?" and I say, "Well, I couldn't see this coming." Now I can sense right away if it's not gonna work. A lot of guys will just instinctively hit on a woman without stopping to think about whether or not they even like her. But I'm way past that. OK. I'm three days past that.
6.
[Q] Playboy: When was the last time you were surprised while picking up your date?
[A] Shandling: I once went out with a beauty queen who actually wore her crown on our date. She was wearing it when she opened the door. She wore it down the hallway and into the car. Soon, I was driving with her wearing a crown. So I said, "Do you need to wear that crown?" And she said, "Not really, but it's a calling card."
7.
[Q] Playboy: It's Garry Shandling's Show is being touted as the heir of the George Burns and Jack Benny legacy. Imagine for us how you might use Burns if he were a guest.
[A] Shandling: I'd probably have him come on and tell me that I'm doing the whole thing wrong. And then I'd have him say, "And I've met you personally and you're not doing that right, either."
8.
[Q] Playboy: You tried to sell your show to the three major networks. All turned you down, and you ended up on Showtime. But now you're getting such rave reviews that common wisdom suggests that the networks made a mistake. In retrospect, did you make the right decision, going with cable?
[A] Shandling: I wanted to do a show where I talked to the camera and played a comedian. That hasn't been done successfully for many, many years. It was a risk for me and the networks, an understandable risk. Showtime was willing to take that risk. In retrospect, I made absolutely the right decision. Had the show been on a network, I would probably have had to make many more compromises.
[A] The whole idea of my work is to be able to do creatively what I want to do. The reason I switched from writing television to performing was that I was creatively frustrated, not that I wanted millions of people to see me. I'm shy. I get nervous in front of millions of people. Seriously. I could never have performed at Woodstock.
9.
[Q] Playboy: Your show's main set is a replica of your house in Los Angeles. When you made that decision and then realized that it would be seen by millions of people, did you have any second thoughts about your interior decoration?
[A] Shandling: No, I was just pleased that you couldn't see the street address from the inside of the set. I thought it might become confusing, two lives that meshed in an abstract sort of way between reality and the show. But I've never lost track of who I am. I've never caught myself talking to the cookie jar instead of the camera or making love to a woman and suddenly looking up for the red light, thinking, Are we on?
10.
[Q] Playboy: What do women still not get right about men?
[A] Shandling: Women need to know that not all guys are going to hurt them the way that guy did right before they started dating me. I know guys I wouldn't go out with.
11.
[Q] Playboy: Your obsession with your hair is nearly as well known as your dating mishaps. What does a woman have to do before you allow her to touch your hair?
[A] Shandling: A woman is never allowed to touch my hair. It's one of the rules--even if I get married, one of the vows we'll be taking is, "promise to love and cherish and. obey and don't touch the hair." The obsession is only a slight exaggeration. I've always thought I look goofy when my hair is flat on top. I'm not one of those guys who come out of the swimming pool looking cool. I look a little like Jerry Lewis. I even have a shower cap that has hair attached to it. Also, when my hair is full, it makes my lips look thinner.
12.
[Q] Playboy: What's the first thing you do in the morning and the last thing you do at night?
[A] Shandling: I have one bad habit. I take an Excedrin when I wake up in the morning. Waking up puts such a crimp in the day. There's nothing I like more than sleeping, and I wake up sometimes and just ache. Excedrin, I guess, is my equivalent of having that cup of coffee in the morning. I also have a banana and some yogurt and some juice.
[A] The last thing I do before going to sleep is to feel the other side of the bed. Comb every inch of the other side of the bed!
13.
[Q] Playboy: Since women are so crucial to your work, should dating expenses be tax-deductible?
[A] Shandling: Yes. In fact, I should be able to claim some dates as emotional dependents. Either way--me on them or them on me. When the tax people say dependent, they really mean physical, don't they? But there should be an emotional-dependency column. Imagine: They call you in for an audit and not only do you have to see the IRS auditor but they have an IRS psychologist. You take in the people you think are dependent upon you emotionally and, you know, have them break down. I could take a girl who says, "God. I need to be with him!" So the IRS says, "OK, we'll give you this one." That's very close, by the way, to a concept that's usable in stand-up. I'll probably jot that down right now and see later if it works. [Scribbles] In fact, it reminds me of another routine I was working on that came out of a friend's experience with group therapy. I said, "Well, how do you pay for that? At the end of the session, do they give you a check and you gotta go, 'OK, who had the heavy neuroses with the side of narcissism? Who had the dependent personality?' "
14.
[Q] Playboy: Did either of your parents warn you about sex?
[A] Shandling: Yes. My mother came into my bedroom and said, "One day you will feel something when you're with a woman. Just don't." And another time, I asked her how the chemicals mixed between the male and the female. And she said, "Go look at the dogs in the front yard. Have you ever seen two dogs?" To this day, I'm afraid of being hosed down while I'm making love.
15.
[Q] Playboy: Have you ever tried to date any of your Tonight Show guests?
[A] Shandling: No. And I'm not just saying that. Believe me. However, I think Bronson Pinchot was coming on to me, but I'm not positive.
16.
[Q] Playboy: With all your Tonight Show experience, you should be able to tell us some tales of the couch.
[A] Shandling: Once, Larry Hagman and I were guests on The Tonight Show. Suddenly, he turned to me while another guest was talking and said, "You like fishing?" I said, "Yeah, pretty much." And Johnny was interviewing somebody! I don't remember what he said next, because I got nervous and turned away. I felt as if I were in school and Johnny was the teacher who would say, "No talking." Another time on the panel, Shelley Winters couldn't stop talking to me. I knew we were going to get caught. She kept saying things about Norman Mailer--to whom Johnny was talking! Stuff like, "Oh, what he's saying isn't right. That isn't how Marilyn was at all." And there I was, caught in the middle. Of course, it's been many years since I've seen Marilyn Monroe. OK, I've never seen Marilyn Monroe.
17.
[Q] Playboy: Which half of which great comedy team would you like to be?
[A] Shandling: Dick Smothers. It would be interesting to see what it would be like if both brothers were funny. [Almost falls over laughing] I'll stand by that. You publish that. I know Tom. I had dinner with him recently and I kidded him the whole night about the fact that I have to go out and do my act alone. He more or less said he had to do the same thing.
18.
[Q] Playboy: How important is a sense of humor on a date?
[A] Shandling: Sense of humor is big with me. When I moved to California from Arizona in 1973, I went to Marina del Rey, which was a real singles scene. I met a girl and she was wearing the tallest platform shoes I'd seen--they were, like, ten inches high. But we were getting along, so I said to her, "When you take those shoes off, do you use them for coffee tables?" She stared at me and said, totally seriously, "No, they're shoes. Why would you use them for coffee tables?" That was it.
19.
[Q] Playboy: What about women are you so sure of that you'd go on the record with it?
[A] Shandling: That they're good in bed.
20.
[Q] Playboy: What are people going to say when they find out you are such a sensitive, introspective guy?
[A] Shandling: "We'd like to send him a gift."
america's funniest strike-out artist explains his love dos and don'ts and why his dating should be tax-deductible
Like what you see? Upgrade your access to finish reading.
- Access all member-only articles from the Playboy archive
- Join member-only Playmate meetups and events
- Priority status across Playboy’s digital ecosystem
- $25 credit to spend in the Playboy Club
- Unlock BTS content from Playboy photoshoots
- 15% discount on Playboy merch and apparel