You're Killing Me! The Playboy Compendium of Outlaw Humor

After World War II, Americans felt entitled to some old-school funny to go with their peace and crabgrass. They'd just put an end to the worst stand-up act in the checkered history of German comedy, and it was time to whip up a few Boston cream pies and break out the exploding cigars. They wanted Bob Hope to be a fast-talking coward, Jack Benny to be an unyielding skinflint and Milton Berle to put on a dress. But things changed in the 1950s. History did not end. There was communism and McCarthyism, war and nuclear proliferation, Emmett Till and Selma, Alabama, the pill and rock and roll. Uncle Miltie in a dress wasn't cutting it anymore.

Others stepped in, others who wanted to talk about politics, sex and race, about hypocrisy, corruption and selfishness, and who thought the best way, or at least one extremely good way, was to make jokes. Jokes about how we did things. Jokes about what we accepted without challenge. Jokes that upset the status quo. And the status quo usually did not joke back. Instead it replied with the institutional powers at its disposal: condemnation, censorship and incarceration.

For more than 50 years outlaw humorists have led charges that conventional wisdom has had to withstand--or succumb to. Such humor--often caustic, sometimes sick but always defiant of authority--is uniquely American in its nonconformity and independence. We've been there. We know. Here then is a pie in the face of tradition.

Animal House

In a world ruled by rules, why not smear mustard on your chest? Or wrap yourself in a bedsheet and pour grain alcohol over your head? These are the kinds of ontological questions that should be raised in the American educational system. In this campus-rebellion flick set before the era of campus rebellions, the merry, mischievous, anarchistic Deltas strike a victorious blow against the Nixon-like Dean Wormer, the militaristic Neidermeyer and all that is cynical, corrupt, regimented, repressed and mustard-free. It represents the career highlights of Doug Kenney, a co-screenwriter and National Lampoon co-founder, and the film's breakout star, John Belushi. Best bit: Belushi's rousing speech after the dean expels the Deltas: "What's all this lying around shit? We just gonna take this? What? Over? Nothing's over until we decide it is. Was it over when the Germans bombed Pearl Harbor? Hell no!"

Roseanne Barr

"My husband said he needed more space. So I locked him outside." With her deadpan sneer and gimlet eye for male foibles, Barr broke into the public consciousness as a five-foot-four, 215-pound self-described domestic goddess. Her sarcasm evoked the real anger roiling blue-collar Middle American womanhood. Those feelings got a fuller expression in her frequently top-ranked television show, a family sitcom not located in the realm of the cute. "I think people get what I'm saying and doing on the show," she told a reporter. "I don't think the press gets it, that it's really anti-glamour. It's really anti everything that the media tries to shove down our throats."

Sandra Bernhard

The first thing you notice is the mouth--shocking in its size and with lips as thick as truck tires. Food trembles in her midst. And when she opens those lips, you know you're in for it. Hilarious in her first big appearance, playing a crazy fan in Martin Scorsese's The King of Comedy, she has become the mistress of a thin but rich domain--the self-anointed, fully realized diva who nonetheless lives in the shadow of such larger stars as Madonna (who is neither outlaw nor humorist). She is frequently capable of going too far, as when she emceed a fashion-industry show in 1992: As Ralph Lauren left the stage after winning an award, Bernhard said, "There's nothing like the sight of a Jewish cowboy riding off into the sunset. I sure do love your sheets, Mr. Lifshitz." Shocking--at least to people who take themselves too seriously.

Lenny Bruce

This is the *sshole who started it all. This c*cksucker was the Elvis of comedy, a talented aggregater of found techniques and coarse street culture. Before he was done he would significantly alter the cultural landscape with his performances, his writing (How to Talk Dirty and Influence People: An Autobiography) and his First Amendment court cases. He was able to synthesize old-time showbiz razzmatazz, Borscht Belt shtick, the X-rated humor of burlesque houses, and pop cultural and political hipness, process the result through his lightning-quick mind and deliver it in very funny jazz inflected routines. He mocked racism by asking the men in the audience if they would rather fuck Kate Smith or Lena Horne, joked about Hitler ("My name is Ben Meltzer, and I am the agent here. We are trying to find a dictator today") and ridiculed religion by treating the world's religious leaders as though they were business conventioneers ("Hello, Johnny! [Pope John XXIII] What's shakin', baby? When are you comin' to the coast? I'll get you the Sullivan show on the 19th. It's good television. Wear the big ring"). Bruce's style has been so thoroughly absorbed into popular comedy that it's a challenge to recognize how new and different he was. And though his period of influence lasted a mere eight years, he succeeded in being not only a revolutionary humorist but--through the stupid and tragically destructive legal actions against him--a revolutionary cultural motherf*cker as well.

Bulworth

A fearless political satire, this film casts a withering, contemptuous eye on the entire system and finds it cynical, hypocritical and corrupt. A politician who tells the truth? What a gag. Warren Beatty has never been funnier or more radical--quite a statement on both counts.

Luther Campbell

He was horny. Yes, he was very horny and he wanted some pussy. Nothing strange about that. Most guys are horny and want some pussy. But this guy, he wanted it so bad he decided to sing out, and that's when things got weird. As Luke Skyywalker, Campbell led the ridiculously explicit 1980s rap outfit 2 Live Crew, whose simple, sexual rhymes ("We Want Some Pussy" was a typical title from its 1986 album, The 2 Live Crew Is What We Are) and Miami bass sound had garnered a big following even before a 1990 obscenity trial in Broward County, Florida made Luke a crossover player. The trial concerned the multiplatinum 1989 album As Nasty As They Wanna Be, which contained "Me So Horny," the first Top 40 single to deal openly with oral-anal sex. His legal defense relied on the First Amendment, though his staunchest defenders struggled to argue the artistic merits of his juvenile humor (despite its clear ties to a long line of sexually explicit black comics such as Redd Foxx, whom Luke sampled). An appeals court dismissal of the obscenity charges went all the way to the Supreme Court before being upheld. With his newfound notoriety, the self-styled black Hef built a business empire on music, home videos and clubs. Thanks to Campbell, musicians no longer have to say "please" when inviting a woman (in song) to "nibble on my dick like a rat does cheese."

George Carlin

Finally, a man who applied Cartesian rigor to the laws of comedy: "I'm in favor of separation of church and state. These two institutions screw us up enough on their own, so both of them together is certain death." Carlin, the baldest of American cynics, forsook a conventional comedy career in the 1960s when he turned from telling jokes to talking about what was inside his head. Carlin is a ridiculer of religion ("First thing they do is tell you there's an invisible man in the sky who's going to march you down to a burning place if he doesn't like you. If they can get you to believe that, it's all over"), and he has little but disdain for any institution. "Prosperity makes it easy enough for Americans not to go ahead and question things. You get a good five-, six-year depression in this country and you'll see some folks out with torches." His most famous routine, about the seven words you can never say on radio, was banned by the FCC, but the bit was less about propriety than linguistics. "Shit, piss, fuck, cunt, motherfucker, cock-sucker, tits. Those are the heavy seven. Tits doesn't even belong on the list. It's such a friendly word. Sounds like a nickname. 'Hey, Tits, c'mon here, man.' Sounds like a snack. New Nabisco Tits. The new cheese tits. Corn tits. Pizza tits. Tater tits."

Catch-22

Naked guys in trees, homicidal whores, shitheaded parade-loving lieutenants and shrapnel-ridden young men unraveling in planes that couldn't get back to base fast enough. Joseph Heller's classic novel brilliantly portrays what happens when a bureaucratic mentality takes over an enterprise as destructive and terrible as war. The hero perversely insists on clinging to his humanity by acting in ways that seem insane--which only goes to prove that he is in fact sane and therefore not exempt from participating in the give-and-take carnage around him. In the years since the novel's appearance we've heard about having to destroy a village in order to save it and having to torture Iraqis in order to liberate them. Heller didn't write those lines; we only wish he had.

Holden Caulfield

"If you really want to hear about it. ..." So begins J.D. Salinger's comic novel The Catcher in the Rye. Caulfield, the teenage narrator, may not recognize himself as a progenitor of half a century of humor, but all the elements are there: the sarcasm, the faultfinding, the unattractive self-absorption, the disdain for phonies, the dread of growing up. You know, like Seinfeld.

Cheech & Chong

Dropping acid while driving, accidentally urinating in laundry hampers, smoking insects--Noel Coward had nothing on these guys. The two itinerant comics--Richard "Cheech" Marin from East L.A. and Tommy Chong from Calgary, Alberta--met in a Vancouver, British Columbia nightclub in the late 1960s and soon after formed a team and headed off on tour. Their act was largely about dope; it veered between political commentary and bloodshot idiocy, with many "Hey, maaaans" sprinkled liberally throughout. Their 1971 debut went gold; 1972's Big Bambu, packaged with a huge rolling paper, was the number one comedy album of the year (an accomplishment back when comedy was consumed on vinyl, not on HBO). By the time 1978's Up in Smoke hit the big screen, Cheech & Chong had become a countercultural phenomenon, Abbott and Costello with a fat spliff. In the opening scene of Smoke (considered by all astute critics the greatest pot movie of all time), they share a supersize joint and gobble hits of acid. Subsequent flicks Next Movie and Nice Dreams repeated the amiable druggies--vs.--Keystone Kops theme to big audiences, but Ed Meese soon made sure nobody found drug use funny. While Chong has suffered persecution typical of a drug crusader (he went to jail last year for selling bongs), Cheech eschewed drug humor in the 1990s, landing a major role on TV's Nash Bridges and a voice role in Disney's The Lion King. This is your brain on drugs, America.

R. Crumb

One shudders to think what might have become of Crumb, a lanky geek who draws grimy little pictures of big girls with huge breasts and huger asses, had he not become the godfather of underground comix. An eccentric refugee from the American Greetings card company, where he was poisoned by flowery sentiment and tawdry emotion, Crumb has variously been described as the creator of the modern comic book, "an American Hogarth, a moralist with a blown mind" (by art critic Robert Hughes) and a "minstrel, artist, poet and philosopher" (by Crumb himself). His classic satires of social strictures and our neuroses emerged through innumerable strips, the most famous of which feature Fritz the Cat, a hepcat who becomes a political radical; Flakey Foont, who never quite figured out who was running things; the con man--saint Mr. Natural; and Whiteman, a businessman who constantly dreams of sex. Who doesn't? Keep on truckin'.

Larry David

That Seinfeld became a phenomenon despite lacking a single sympathetic character was a testament to its writing. Then co-creator Larry David topped himself with Curb Your Enthusiasm. The show's premise is that a rich man, liberated from all bodily wants, all need, all labor and all care, will nonetheless behave in ways that are mean, cowardly, vain, ignoble and utterly self-serving; that in most circumstances, efforts to overcome that impulse and act with generosity and kindness will be rebuffed, ridiculed and met with behavior that is mean, cowardly, vain, ignoble and utterly self-serving; and that ultimately the best way to counter such behavior is to be more mean, cowardly, vain, ignoble and self-serving.

Doonesbury

For decades Doonesbury has been sharp and sardonic, much like the generation whose attitudes and foibles it recorded so well. During the 1970s and 1980s, when boomer interests and appetites ruled the world uncontested, Doonesbury was essential reading. Now that boomers have been elbowed into sharing the cultural limelight with Gen Xers, Gen Yers and children still too young to be captured in journalistic shorthand, Doonesbury seems more comfortable replacing its undercurrent of outrage with a more resigned--but wiser--outlook on life.

Dr. Strangelove

Or: How I learned to stop worrying and love the bomb

A mushroom cloud, the end of the human race as we know it, utter and complete devastation--now that's funny! The blackest comedy Hollywood has ever produced, Dr. Strangelove plays the insane logic of the Cold War completely for laughs. Stanley Kubrick tells a story that keeps folding in on itself until there's no hope for a happy ending. Even so, the climax is a hoot: The sight of ignorant cowboy Slim Pickens riding a falling hydrogen bomb, yee-hawing his way to our mutually assured destruction, is one of the most iconic images ever filmed. In a movie filled with funny scenes, perhaps the funniest element is the disciplined, deadpan delivery with which the actors discuss nuclear annihilation. It's the same somber, sanitized, euphemism-laden language our leaders so often use to discuss war, except somehow we don't usually laugh; we just nod our heads and agree.

Election

Set in a Midwestern high school, Alexander Payne's 1999 film is the best satire of American politics since The Candidate. Reese Witherspoon's determined, ambitious, ruthlessly nice Tracy Flick is scary--a power grabbing survivor in a ponytail--and Matthew Broderick is also funny as the weak, inept teacher who aims to thwart her.

Flavor Flav

In Public Enemy, one of the most important--and the most stridently political--groups in hip-hop history, Flav was the ghetto clown. With an enormous clock hanging from his neck (counting down to Armageddon, no less) and his signature "Yeeeaaaah, boyeee," he alleviated the menace in Chuck D's Marv Albert baritone and the militarism of PE's Black Panther shtick. His erratic offstage behavior only added to his comic edge and genuine outlaw status. He delivered half his exclamations in a screech or a snicker, and much of the rest were hilariously inscrutable. He recorded "911 Is a Joke" on Fear of a Black Planet--a satire based on a serious problem and, alas, no joke.

Redd Foxx

Much of Foxx's humor was in the delivery--often by default, since half the time nobody could understand what the hell he was saying. Yes, he played Fred Sanford on Sanford and Son--even a big dummy knows that. Foxx was also known as the dean of blue comedy, cutting his first album, Laff of the Party, in 1955; he eventually produced 54 party records, which, without airplay, promotion or a presence in most retail stores, would eventually sell 20 million copies. "Pretty soon, vital-organ transplants will be the thing," goes one joke. "Imagine a white guy in the shower looking like a panda." His humor wasn't all bawdy; it was satirical as well. "See, blacks have had whites fooled for years with one word: boss. 'Good night, boss!' 'Yassir, boss!' See, boss spelled backward is double-s-o-b." Breaking in at a time when blacks weren't allowed to play white clubs, Foxx performed comedy for black people in the vernacular, breaking ground that Richard Pryor and Eddie Murphy would later mine.

The Graduate

"I just wanna say one word to you. Just one word--plastics." With that single line, what would have been a quirky bedroom farce about a mixed-up kid in an unusual love triangle becomes a satire about a young man who feels suffocated by the banality, the boredom--the plasticity!--of his parents' world. How great was this film? We laughed. We cried. We thought extensively about hot mother-daughter combinations. And then we bought the soundtrack. Two thumbs up.

Dick Gregory

"I've got to be a colored funnyman," Gregory would say, "not a funny colored man." A noted comic in the 1960s, he was also a prominent activist; running as a write-in candidate for president in 1968, he received more than a million votes. (Some accused him of taking the election from Humphrey and handing it to Nixon, à la Nader in 2000.) His jokes first and foremost challenged the political order by showing intelligence, a capacity supposedly beyond blacks. "The NAACP asked me to buy a lifetime membership. Told them I'd pay a week at a time. Hell of a thing to buy a lifetime membership, wake up one morning and find the country's been integrated." Often heckled mercilessly, he defused the tension when an audience member called him a nigger by explaining that his contract stipulated he was to get $50 whenever someone shouted the word at him. "Now will everybody in the room please stand up and yell, 'Nigger'?" Now that's courage. Try that in a public place someday and see what happens.

Heathers

Forget Mean Girls. Michael Lehmann's 1989 darkest of dark comedies is sharper, smugger and far more audacious. The popular girls, for example, don't learn any lessons; they simply die. Winona Ryder demonstrates why everyone thought she would become a major star, and Christian Slater offers the best Jack Nicholson performance that Nicholson never gave. Rent it--it'll be a long time before you see another high-school-shootings comedy.

Bill Hicks

Only his 1994 death at the age of 32 prevented the most lacerating comedian of his generation from becoming a major something: cultural force? national conscience? scourge? talent-show judge? "During the Gulf war, intelligence reports would come in--Iraq has incredible weapons. How'd we know that? Well, we looked at the receipt." "Clinton's a liar and a murderer. He launched 22 cruise missiles against Baghdad in response to the alleged assassination attempt of President Bush. Six innocent people in Baghdad are dead, and the U.S. has spent $22 million. What we should have done is get rid of Bush ourselves." "This is my final live performance. I'm quitting because I finally got my own TV show. It's called Let's Hunt and Kill Billy Ray Cyrus." When he died, he left no prisoners.

Abbie Hoffman and Jerry Rubin

Founders of the yippies, they ran a pig for president decades before the thought ever occurred to Karl Rove. Their best gag? Assembling 50,000 people in a Pentagon parking lot and chanting in an effort to levitate the building. They stood in the visitors' area of the New York Stock Exchange floor and threw money down just to watch the traders scramble for the bills. Hoffman titled his book Steal This Book. What he really meant was, "Don't pay the store. Send the money straight to my bank account!"

Hungry I

This joint in San Francisco's North Beach is now a late-night topless club--but it was something to see back in the day. The Hungry I became the Plymouth Rock of outlaw humor when Mort Sahl debuted his act there in 1955. A small, smoky downstairs place, the club--originally the Hungry Id but shortened "to show we weren't white-bread," says owner Enrico Banducci--became the place for offbeat, antiestablishment, "sick" comedians to perform, as well as a stopover for folk music acts such as the Kingston Trio. The club featured one of the chief semiotic signatures of stand-up comedy--the brick wall--and provided a model for the programming at other clubs, including the Purple Onion in San Francisco and Cafe Wha? in New York.

Don Imus

Drugs and alcohol almost ended his successful career as a disc jockey, but the reborn I-Man is a high-on-life news junkie. Resident provocateur on the New York--D.C. shuttle, he's become a bit like Charlie Rose, if only Rose were snarkier and had done more to abuse himself. Imus maintains a wicked wit; in his finest moment, at the Radio & Television Correspondents' Association annual dinner in 1996, he flayed all in attendance. That included President and Mrs. Clinton, whom he teased about Whitewater and sex before cracking wise about others on hand. On Dan Rather: "He's a little tense. Watching Dan Rather do the news, he looks like he's making a hostage tape." On Peter Jennings: "The first place the telecommunications bill should have mandated a V-Chip be placed is Mr. Jennings's shorts." On Tim Russert: "He once worked in New York for Senator Moynihan and Governor Cuomo. His duties included hiding the bottles for Pat and the bodies for Mario."

Jackass

The name says it all. Through their baffling willingness to endure needless pain, this group of geniuses has managed to score a TV show, a movie and (in some cases) embryonic acting careers. As Aristophanes proved, there's really no better entertainment than watching a guy smack his friend in the nuts with a sledgehammer. The Jackass stunts--think Three Stooges for Ritalin users--horrify the audience, which then laughs at its dismay. How better to protest the parents who made you take honors chemistry and sent you to soccer camp than by covering yourself with shit? (Or at least laughing at guys who do.)

Andy Kaufman

Perhaps the only recent comedian to work in metatext, Kaufman strove not to entertain people but to make them wonder what the hell was wrong with this guy. His shows were often a test of an audience's psychological endurance: A so-so riff might become, through perseverance, amusing, then riotously funny, then not quite funny and then just painful to watch. He was the fragile-looking weirdo lip-synching the theme from Mighty Mouse on Saturday Night Live and the nonsensical foreigner Latka Gravas on Taxi. Those were his good days. He challenged women to wrestle, then declared himself broke on the Letterman show and relentlessly panhandled the audience until he had to be removed by security (the sole thankful suppression of outlaw humor). He appeared on the Taxi set as his alter ego, the boorish Tony Clifton, annoying everyone until Judd Hirsch throttled him and security again had to haul him off. (Kaufman considered this particular moment the pinnacle of his professional life.) Kaufman was much more a performance artist than a comedian, which might have been more obvious if he hadn't done all his work in comedy clubs and on entertainment shows.

Sam Kinison

This wild and profane former Pentecostal minister practiced yelling as an art form, delivering blasts of crazed rage infinitely more promising than any Howard Dean yawp. In volcanic tirades, Kinison's anger would rise like lava until he seemed to explode, abandoning words for the say-it-all profundity of "Auuugh-auuugh!" In a subtle parody of the old Troggs hit, the ever-cuddly Kinison shouts "Wild thing /You made me trust you, then stuck the knife in my heart, you lying, unfaithful, untrustable tramp!" On the famine in Ethiopia: "I've figured out why you people are starving. It's because you live in a desert. Yes, a desert! See this? This is sand! Nothing will grow here!" On modern religion: "Jesus is still up in heaven, thumbing through the Bible, going 'Where did I say to build a waterslide?'" At the time of his death, Kinison had just married and appeared to be settling in for the long haul. "How many times do these relevant underground comics have to OD and die?" he once asked. "It's been done. It's cliché. I'm not like that. I come from a relationship with God, which I still have."

Tom Lehrer

For several years in the late 1950s and early 1960s, the bookish Lehrer was considered the equal of Lenny Bruce, Dick Gregory and Mort Sahl. He attained this status by being the most brilliant practitioner of an arcane but high art form: writing and performing satirical songs. Among them: "National Brotherhood Week" ("It's only for a week, so have no fear./Be grateful that it doesn't last all year"); "So Long, Mom (A Song for World War III)" ("So long, Mom, I'm off to drop the bomb. /So don't wait up for me. I'll come back to my home when the war is over,/An hour and a half from now"); "The Masochism Tango" ("Take your cigarette from its holder/And burn your initials in my shoulder"); and "The Old Dope Peddler" ("When the shades of night are falling,/Comes a fellow ev'ryone knows./It's the old dope peddler/Spreading joy wherever he goes. /He gives the kids free samples/Because he knows full well/That today's young innocent faces/Will be tomorrow's clientele"). It's no Tenacious D, but they liked it back then.

Bill Maher

The man who cracked the first AIDS joke on a network (to Carson: "I just want to meet an old-fashioned girl with gonorrhea") later singlehandedly reintroduced political comedy to mainstream TV. Maher usually stayed within the boundaries of acceptably spirited discourse for Politically Incorrect--no one was ever considered sufficiently loathsome or repugnant that they or their champions couldn't appear on the show and break bread with him. Yet Maher was pushed from outspoken to outlaw after September 11, when he not only agreed with a conservative guest that the 9/11 terrorists were not cowards but maintained that America had behaved in a cowardly way. "We've been lobbing cruise missiles from 2,000 miles away. That's cowardly. Staying in the airplane when it hits the building...it's not cowardly." This frankness earned him a menacing slap from presidential press secretary Ari Fleischer, who warned that Americans "need to watch what they say, watch what they do." Sponsors canceled ads, and ABC eventually canceled the show. Maher's martyrdom lasted until early 2004, when HBO hired him.

Mash

Humor is misery distilled, and nowhere will you find more misery than at a mobile hospital near the front lines of a nasty war fought with conventional weapons. Happily antiauthoritarian but at the same time highly moral, Robert Altman's 1970 film cleverly swipes at the madness of war and the mindlessness of the military. It's the ultimate moment for antiheroes. The good guys--the doctors who care--tell misogynistic jokes, get drunk and act like assholes, while the bad guys play by the rules. How dark was MASH? The theme song, which was also used in the TV version, had a name: "Suicide Is Painless." It even had little-known lyrics: (Sing along now) "Suicide is painless./It brings on many changes. ..."

Michael Moore

Moore has proven the master of a particular kind of humor--the it's-funny-because-it's-true kind of joke, the look-at-all-the-dead-people kind of funny. The contentious and weighty documentarian first achieved cinematic success with Roger & Me, a sharp, affecting film about what happens when a dim-witted giant corporation, in this case General Motors, shuts down a plant. Moore reliably takes a left-wing position on issues but often surprises with a bit of blue-collar conservatism--and surprises even more with a wicked wit. Moore's Bowling for Columbine, a look at guns and gun control, won an Oscar. His Fahrenheit 9/11, about President Bush and his foreign policy, won the Palme d'Or at Cannes. This should ensure Moore a long career--look how popularity in France has helped Mickey Rourke.

Eddie Murphy

When Murphy broke, little did anyone expect that Daddy Day Care and The Haunted Mansion would be in his future. Brash, gifted and willing to take risks (example: the 1997 bust in which he got snagged with a 20-year-old Samoan transvestite prostitute...whoops), Murphy seemed destined to do as a movie star what Richard Pryor had done as a comedian (but not as a movie star): use humor to bring light and uncomfortable heat to race relations. It was a shocking, searing sensation to hear him say, in 48 HRS, "I'm your worst nightmare--a nigger with a badge," and the uneasiness between him and white people in Trading Places and Beverly Hills Cop gave those films a distinctive edge. Murphy for some reason decided that he preferred being an entertainer to being an artist, and he now serves the cause of brotherhood by inspiring people of all races to denigrate The Adventures of Pluto Nash.

National Lampoon

Between the decline of the early-1960s topical comic--Gregory, Bruce, Sahl--and the arrival of Saturday Night Live, outlaw humor lived not in clubs or on TV but in the pages of a magazine. Smart, funny and as daring as anything produced by mostly 20-somethings playing with other people's money can be, National Lampoon amused a generation with a combination of scalding irreverence and loopy nostalgia. Though it was happy to take on big targets--Nixon, Agnew, Jesus, sex--it also scored by teasing with affection but without sympathy the pretensions, foibles, zits, sexual inadequacy and lunkheadedness of ordinary Middle American life. In its heyday the magazine had a monthly circulation of 800,000, (more than Esquire has today), produced a series of successful stage shows and albums and eventually launched a movie brand name that produced Animal House and the Chevy Chase Vacation flicks. Eventually, however, the talent drifted away and new recruits couldn't keep up the circus act. National Lampoon waddled through a long, dwindling decline, and the brand now leads a zombie-like (continued on page 150) Outlaw Humor (continued from page 108) existence, popping up with movies such as Dorm Daze and Van Wilder.

Portnoy's Complaint

Long before Philip Roth became a man of letters, he was a very funny novelist who, when his hands weren't busy in his pants, whacked out hilarious stories on the typewriter. Nowhere is this better demonstrated than in Portnoy's Complaint, a novel in which sex-driven, sex-besotted and sex-obsessed Alexander Portnoy bares his psyche and his soul, which America found greatly amusing. American Pie got its pie idea from Portnoy's defiling of the family calf's liver.

The Producers

Today the tune "Springtime for Hitler" is about as shocking as a gay sex scene on HBO. But there was a time--1968, actually--when making a joke of a genocidal dictator who instigated a war that claimed more than 50 million lives was thought to be off-limits. Mel Brooks shattered the taboo with a swastika-draped parody of Broadway musicals, presenting Hitler as a demented hipster. Brooks also deserves recognition for the hilarious Blazing Saddles, though one can't help but think that most of the outrageous racial material was inspired by one of the film's co-writers, Richard Pryor.

Richard Pryor

Pryor on interracial dating: "Don't ever marry a white woman in California. A lot of you sisters probably sayin', 'Don't marry a white woman anywhere, nigger. Shit! Why should you be happy?'" On the difference between how whites and blacks date: "Whites say, 'Good night, dear. Been a pleasure being with you.' Blacks say, 'Nigger spend $34, somebody givin' up somethin'!'" On the LAPD accidentally killing a black man with a choke hold: "Ah shit, he broke. Can you break a nigger? Is it okay? Let's check the manual. Yep, page eight, you can break a nigger." Following a wave of black comedians whose essential message was "I'm black, and I'm the same as you," Pryor broke through by proclaiming, "I'm black and I'm different." Pryor took on police harassment, drug use, crime and sexual attitudes between the races. "Ain't no niggers goin' to the moon, you know that. First of all, ain't no niggers qualified, so you all tell us. If niggers was hip, they'd help you all get to the moon. 'Hey, man, let's organize and help these white motherfuckers get to the moon so they leave us alone.'" Pryor's humor was honest, frank about taboo subjects such as sex, open about blacks' view of whites and blacks' view of themselves.

Chris Rock

Rock is best when, as with his black-people-vs.-niggers routine, he's slamming black orthodoxies: "Niggers always want credit for some shit they're supposed to do. They'll brag about stuff a normal man just does. They'll say something like, 'Yeah, well, I take care of my kids.' You're supposed to, you dumb motherfucker! 'I ain't never been to jail.' Whaddaya want--a cookie?" Rock on single mothers: "It doesn't take a scientist to tell when you're going to have fucked-up kids. If a kid calls his grand-mom Mommy and he calls his mama Pam, he's going to jail."

Mort Sahl

Despite his newspaper and crew-neck sweater, mild-mannered Sahl was the first of the outlaw comedians. Poised against a sea of guys in plaid jackets telling mother-in-law jokes, Sahl drew younger, hipper audiences with his wisecracks about politics, trends and fads. His breakthrough joke was a slap at Senator Joe McCarthy ("Have you seen the Joe McCarthy jacket? It's like an Eisenhower jacket only it's got an extra flap that fits over the mouth"). He was an equal-opportunity satirist, taking shots at the golf-loving Eisenhower ("Ike was going to walk a little black girl to school in Little Rock by the hand, but he couldn't decide whether to use an overlapping grip") and at causes ("I'm for capital punishment. You've got to execute people. How else are they going to learn?"). Rants about the Warren Commission caused a career nosedive in the 1960s, but he continues to perform, his act now enriched by experience: "In the 1960s you had to be Jewish to get the girl; in the 1970s you had to be black to get the girl; in the 1980s you had to be a girl to get the girl. What's left?" (Mort was in fact married to Playboy's Miss August 1964, China Lee.)

Saturday Night Live

The idea alone was brilliant: Round up the funniest, most talented comedians from all over the place, give them a week to come up with material, turn a blind eye as some of them power-snort buckets of cocaine, then push them onto a live stage where the cameras are rolling. "Live from New York, it's Saturday Night!" Written by and starring many of the people (among them Anne Beatts, John Belushi, Chevy Chase, Michael O'Donoghue and Gilda Radner) who had made National Lampoon's magazines, albums and stage shows such successes, the program became an on-air clubhouse for that same spirit, though much watered down. Never as acidulous as Lampoon, SNL nevertheless acquired a reputation for danger just by poking fun at such fat targets as Gerald Ford's clumsiness and the false seriousness of television news, simply because nothing else on TV was doing anything like it.

The Sex Pistols

The band that changed the face of rock and roll was instigated as a fashion-scene joke by oily promoter Malcolm McLaren, whose gift is knowing how to stir things up. McLaren, who had briefly managed the New York Dolls, assembled a band largely from the hangers-on at his clothing store. Fronted by a sarcastic, unemployed rotter and anchored by a proto-loser "bass player," the Sex Pistols took to the stage, snarling and making a racket. Never mind that they weren't good at playing their instruments: The band signed with a major label. They released the album Never Mind the Bollocks, Here's the Sex Pistols, with the singles "Anarchy in the U.K." and "God Save the Queen" ("God save the queen,/ The fascist regime"). The Pistols didn't last long, but their legacy was enormous, as evidenced by countless neo-punk emulators, most of whom, sadly, never got the joke.

Sick, Sick, Sick

Jules Feiffer's cartoon strip, which first appeared in The Village Voice in 1956, dealt with nuclear apocalypse and racial intolerance, as well as sexual inadequacies, romantic anxieties and all matters in between. Feiffer's humor was often ironic or absurdist, leading to the sort of mordant jokes that invited less than hip audience members to say, "That's sick!" Hence the strip's original name, which was applied to many young humorists, including Lenny Bruce. Feiffer was one of the few who made his weird humor work in mainstream movies. Carnal Knowledge, which starred Jack Nicholson, was his vicious--and funny--look at dysfunctional relationships between the sexes, a cynical view best described by a line Feiffer cut from the script: "Boys begin life not liking girls. Later they don't change; they just get horny."

The Simpsons

It's hard to think that a show can be outlaw when ancillary products bearing the leading characters' likenesses are found in so many of the world's emporia. Yet is there a better word to describe a program that, in its good-natured but merciless way, makes such devastating fun of parenthood, business, industry, government, religion, education, the law, science, progress, Habitat for Humanity and old rock stars--to name just a few of the institutions the show has found less than sacred? And by the way, a little gossip: Smithers is as gay as a tree full of birds. You didn't hear it from us.

Kevin Smith

He earned his place on this list with Dogma (1999), a pro-God, pro-faith film that managed to outrage conservatives by suggesting that an abortionist might be a relative of Christ, a stripper might be a kind of angel, a 13th apostle might be a malcontent, and Alanis Morissette (and presumably not Eric Clapton) might be God. Catholics groused, and Disney, parent company of the distributor Miramax, forbade Miramax to back it. But the film came out, and militant godsters were later rewarded with The Passion of the Christ. Now Smith is signing on to hawk products in TV ads and make mainstream films. Hey, even outlaws have to eat.

South Park

Is it funny to kill a tiny, near-mute child? Maybe not the first time, but by the 16th go-round it kind of brings a warm chuckle. Matt Stone and Trey Parker's daringly low-tech animated series about gutterhead fourth-graders in a dysfunctional Colorado town has a good time picking on fat, juicy targets, including the hypocrisy of Americans' attitudes toward race, violence, religion, homosexuality, environmentalism and especially the entertainment media. As one critic put it, "Kids these days say the darnedest fucking things." Stone and Parker's magnum opus is the feature film South Park: Bigger, Longer & Uncut, the most inspired moment of which casts Satan as Saddam Hussein's lovesick boyfriend.

Howard Stern

The King of All Media built his empire on Lesbian Dial-a-Date, Stuttering John and songs about queefs. But now he's defending his domain against an assault from federal bluenoses and craven corporate moralists. The secret of his success: allowing the uncensored voice inside each of our heads--which in his case is cleverer, meaner and more incautious--to escape. It's little wonder Stern has had limited luck on television; his humor is cerebral and verbal and, apart from the strippers undressing, not particularly visual. Stern's ideas spring straight from the id, which has certainly helped him become America's pioneer in radio sexuality. Not bad for a guy who claims to be "hung like an acorn."

Hunter S. Thompson

In 1971, with the hippy-dippy 1960s in full retreat, drugs were no laughing matter. With a meandering tale of an easily distracted sportswriter, Thompson rectified that perception. "We were somewhere around Barstow on the edge of the desert when the drugs began to take hold," begins Fear and Loathing in Las Vegas. "I remember saying something like 'I feel a bit lightheaded; maybe you should drive.' And suddenly there was a terrible roar all around, and the sky was full of what looked like huge bats, all swooping and screeching and diving around the car, which was going about a hundred miles an hour with the top down to Las Vegas. And a voice was screaming: 'Holy Jesus! What are all these goddamn animals?'"

Wag the Dog

How frustrating is it to be a satirist? In 1997 Barry Levinson made a smart, sly movie about a president who starts a war to distract the country from his sexual peccadilloes. Not a year later our president bombed a terrorist base, and many people believed he did it to distract the country from his sexual peccadilloes. Here's the punch line: Many of those who thought that at the time now say he should have done more to fight terrorists.

John Waters

Waters's camp films earned him the title the Pope of Trash from no less an authority than William S. Burroughs. (He's also been called the Prince of Puke.) Pink Flamingos, for example, tells the story of Babs Johnson (played by Waters's muse, the big-and-tall transvestite Divine) and how two jealous perverts (as the script calls them) try to steal her Filthiest Person Alive title by sending her a turd in the mail and burning down her trailer. Pink Flamingos ends with one of the most edifying scenes in film history, in which Divine eats a fresh piece of dogend off the sidewalk. Says Waters, "I'm not interested in using sex to turn people on. If anything I use it to make people laugh. I mean, has anyone ever masturbated to a John Waters movie? I doubt it. If they have, they probably need help."

Will & Grace

God bless American prime-time TV planners: It took them 50 years to figure out that neurotic gay men are the funniest people on the planet. And nothing subverts like success: All but the most ignorant viewers embraced quick-witted queers Will Truman and Jack McFarland, whose innuendo-laden exchanges make the banter on Friends sound like study tapes for third-year dorkese.

The Top 25

1. Lenny Bruce

2. Richard Pryor

3. Howard Stern

4. Andy Kaufman

5. Sam Kinison

6. George Carlin

7. Hunter S. Thompson

8. R. Crumb

9. John Waters

10. Mort Sahl

11. Chris Rock

12. Tom Lehrer

13. Roseanne Barr

14. Bill Maher

15. Don Imus

16. Dick Gregory

17. Michael Moore

18. Sandra Bernhard

19. Kevin Smith

20. Redd Foxx

21. Larry David

22. Bill Hicks

23. Bart Simpson

24. Cheech & Chong

25. John Belushi

And five who will never be outlaws

1. Yakov Smirnoff

2. Jeff Foxworthy

3. Judy Tenuta

4. Gallagher

5. Sinbad