Wizards of Wit – Part 3


by Arie Kaplan

PART III: 1990-2002

From the Margins to the Mainstream

In the early 1990s, the children of America’s baby boomers–the second generation raised on television–came to be known as Generation X, a label that signified their unsure place in the world. Unlike their parents, they deferred marriage after college to pursue their dreams of lucrative and glamorous careers. The Jewish comedy writers of this period played on the “Gen X” mentality of self-fulfillment and indulgence in scripting films and television programs which spoofed their self-centeredness. And Jewish performers in the ’70s and ’80s who had been largely relegated to supporting roles now emerged as the leads in popular TV sitcoms such as Seinfeld and Friends. So, too, some of the principal characters had Jewish identities, such as Grace Adler in Will and Grace and Kyle Broflovski in South Park–a stark contrast to the ’70s, when Jewish characters, such as Archie Bunker’s Jewish niece Stephanie, had only supporting roles. The public’s acceptance of this phenomenon affirmed that “Jewishness” had finally become an integral part of America’s pop-culture landscape.


“If I’m the best man, why is she marrying him?”   –Jerry Seinfeld

In November 1988, comedian Jerry Seinfeld (a frequent Tonight Show guest) sat across from his longtime friend Larry David (a former writer for Saturday Night Live) at the Westway Diner in midtown Manhattan and bemoaned his inability to create a sitcom vehicle that reflected the “Seinfeld brand of humor”–astute observational comedy. They conceived of a sitcom which would recall classic television: Jerry Seinfeld, like fellow Jewish comedian Jack Benny before him, would play himself, a comedian beset by life’s trials and trivialities.

Seinfeld premiered in May 1990 to a tepid response. “We were fortieth in the ratings,” recalls Seinfeld writer Tom Leopold, “but network execs just left it on. Now they’d kill it after six episodes–but because it stayed on and it was funny, word of mouth did the rest.”

Spearheaded by Jewish head writer Larry David (the inspiration for Jerry’s friend George Costanza, portrayed by Jason Alexander), assisted by Jewish writers Tom Leopold, Carol Leifer (the model for the character of Jerry’s friend Elaine Benes, portrayed by Julia Louis-Dreyfus), and Dave Mandel, Seinfeld soon emerged as the hippest sitcom in America. “People said it was ‘a show about nothing,'” says writer/performer Robert Smigel (SNL, TV Funhouse), “but it had the most dense plotlines. It was about the minutiae, the minor annoyances that define our everyday lives.” Seinfeld’s character reflected the ambitious Jewish man of the ’90s who is unable to make a commitment to a woman, breaking up with girlfriends for trivial reasons; in one episode he dropped a woman for wearing the same dress every day. Lawrence J. Epstein, author of The Haunted Smile, sees Seinfeld’s indecisiveness in matters of love as a metaphor for the inability of many American Jews to affirm their Jewishness. “The longstanding tension between Jewish and American identities is partially overcome in Seinfeld,” Epstein writes, “by having the characters not choose at all, by refusing to be grown up enough to have to choose.”

Seinfeld‘s brand of humor was “a neurotic Jewish craziness and narcissism that just captured America,” comments comedy legend Carl Reiner (Your Show of Shows, Oh, God!). In one episode, Jerry’s friend Kramer (Michael Richards) meets Jerry’s Jewish girlfriend, who keeps kosher (“Wow! You’re so pious…when you die, you’re going to get some special attention”). Later on, Kramer stops her as she is about to succumb to the temptation of eating lobster. “You saved me,” she says. “I knew you’d regret it for the rest of your life,” he replies. In the end, however, George (Jason Alexander) tricks her into eating the forbidden food. This twist reveals the essence of Seinfeld: comedic interplay between kindness and cruelty.

Seinfeld‘s writers, however, did not condone heartless behavior. In the final episode, Jerry and his friends land in prison for standing idly by as a man is robbed of his car. The show’s closing message: even in Seinfeld‘s amoral universe, one cannot escape ethical responsibility.

With its openly Jewish leading man and Jewish themes, Seinfeld, the most successful sitcom of the ’90s, was a watershed in the portrayal of Jews on TV.


“Um, because if Santa and the Holiday Armadillo are even in the same room for too long, the universe will implode!”
–Santa Claus (Matthew Perry), when Ben (Cole Sprouse) asks why the Holiday Armadillo (David Schwimmer) has to go away, on Friends

In 1994, a new sitcom focused on six single New Yorkers, two of them Jewish. Created by Jewish comedy writer Marta Kauffman and her writing partner David Crane, Friendsexplores the lives of these twenty- and thirty-something platonic friends, lovers, roommates, and siblings who form an extended family. In a classic episode, Ross Geller, a single Jewish father (played by David Schwimmer), tries to teach his young son Ben (Cole Sprouse) about the meaning of Hanukkah. Ben, who’s been celebrating Christmas (Ross’s ex-wife is Christian), can’t imagine not having a visit from Santa. To please him, Ross sets out to buy a Santa suit, but can only find an Armadillo costume. Dressed as the “Holiday Armadillo,” he wishes Ben a “Merry Christmas” and “Happy Hanukkah.” Ben then asks, “Are you for Hanukkah too? Because I’m part Jewish!” Elated by his son’s reaction, Ross tells his friends: “I’m finally getting him excited about Hanukkah!” The episode’s message: with so much intermarriage, divorce, and assimilation, it isn’t easy for a young Jewish single in a state of limbo to raise a child with his Jewish identity intact.

Interfaith couples became commonplace in ’90s sitcoms. In The Nanny, an outspoken, self-spoofing Jewish nanny (played by Jewish actress Fran Drescher) eventually married her proper English employer. Dharma and Greg explored the comedic contrasts between a new age Jewish hippie and her button-down WASP businessman husband. Mad About You delved into the lives of Jewish filmmaker Paul Buchman (Paul Reiser) and his beautiful non-Jewish wife Jamie (Helen Hunt). In stark contrast, a generation earlier, the 1972 series Bridget Loves Bernie (about the relationship between a Jewish man and his Irish Catholic wife) had to be cancelled because of protests from both the Jewish and Catholic communities.


Grace: “Well, what makes you think that you have the better candidate?”

Will: “Grace, he’s gay.”

Grace: “Well, mine’s a woman and Jewish. That makes two victims to your one.”

–Will (Eric McCormack) and Grace (Debra Messing) arguing about political candidates, Will and Grace

Will and Grace, a comedy series featuring a gay male lead, broke new ground when it premiered on network TV in fall 1998. Created by David Kohan and Max Mutchnick (both Jewish), the show explores the platonic relationship between Will Truman (Eric McCormack), a gay WASP lawyer, and Grace Adler (Debra Messing), a heterosexual Jewish interior designer. In addition to its honest portrayal of homosexuals, the series is trailblazing in its depiction of a beautiful, proudly Jewish female lead who is refreshingly free of negative stereotyping. In the “Cheaters” episode, for example, Grace discovers that Will’s married father George (Sydney Pollack)has taken a mistress, Tina (Lesley Ann Warren). Grace informs a disbelieving Will, who then invites his father and Tina to dinner. Frustrated by the triviality of the conversation, Grace takes Will aside and explains that, in her Jewish family, a matter of such gravity would have been put on the table before the appetizer. Will counters by saying that, in his family, that’s not the way things happen. Finally, as a result of Grace’s prodding, Will and his father engage in a long-overdue heart-to-heart. The show’s portrayal of a Jewish woman as emotionally forthright and honest contrasts sharply with Woody Allen’s depiction of Alvy Singer’s loud and outlandish Jewish family in Annie Hall.


“Hanukkah is the festival of lights,

Instead of one day of presents, we have eight crazy nights!

When you feel like the only kid in town without a Christmas tree,

Here’s a list of people who are Jewish, just like you and me!”

–Adam Sandler, “Hanukkah Song”

In 1993, Saturday Night Live producer/writer Lorne Michaels (born Lorne Lipowitz) tappedSimpsons and SNL writer Conan O’Brien to host NBC’s Late Night. Renamed Late Night with Conan O’Brien, the revamped show was built around comedy sketches rather than celebrity interviews. Conan’s handpicked head writer Robert Smigel seized this opportunity to add Jewish content, casting himself as Ira, Conan’s ineffectual, sleazy agent, satirizing the stereotypically Jewish Hollywood powerbroker. Later, Smigel introduced perhaps the show’s most successful character, Triumph the Insult Comic Dog, a talking-dog puppet (with a Russian accent reminiscent of Smigel’s immigrant Jewish family) who conducted celebrity interviews while parodying such Jewish Borscht Belt comedians as insult comic Don Rickles and Yiddish dialect comedian Myron Cohen.

In the ’90s, Jewish parodies on Saturday Night Live reflected two contrasting comedic impulses: the audacious Lenny Bruce and the amiable Adam Sandler. In the Brucian tradition, Jewish writer Hugh Fink satirized network TV’s rush to air Christmas specials while ignoring Chanukah. In his SNL sketch “And So This Is Chanukah,” Fink had pop icon Britney Spears (played by Christina Ricci) deliver the line: “Chanukah is a special holiday, where we as Christians take time out to think about forgiving our Jewish friends for killing our Lord.” Reaction was swift. “The head of the Anti-Defamation League was all over the national press,” recalls Fink, who attributes the backlash to the politically-correct climate of the ’90s. “Al Franken had done jokes about Jews killing Jesus years earlier, but back then, Jewish groups didn’t bat an eye.”

In contrast, Adam Sandler’s ethnic-pride anthem “Hanukkah Song,”–a celebratory “who’s a Jew” in song (“Some people think that Ebenezer Scrooge is / Well, he’s not, but guess who is? / All Three Stooges!”)–set off no alarms at the ADL. “Adam takes his role as a stereotype-breaker very seriously,” says longtime friend and collaborator Robert Smigel. “He grew up in New Hampshire, where he had to deal with antisemitism; now he likes being a strong role model for Jewish kids. A lot of Jewish role models in comedy have been the nebbish, the nerd, the loser, the self-deprecating guy. Adam feels really good about saying, comedically, you don’t have to be the geek; the fact that you’re Jewish doesn’t mean you’re any less cool.”


“Thou shall not kill. Thou shall not commit adultery. Don’t eat pork. I’m sorry, what was that last one? Don’t eat pork? Is that the word of God, or is that pigs trying to outsmart everybody?”

–Jon Stewart

On January 11, 1999, Craig Kilborn, the smarmy host of Comedy Central’s late-night news parody The Daily Show, turned over the reins to whip-smart writer/comedian Jon Stewart (a.k.a. Jon Stewart Liebowitz). Stewart, who is also executive producer, writes much of his own material for the revamped show, which was renamed The Daily Show with Jon Stewart.

An adept and witty political satirist in the tradition of Mort Sahl and Lenny Bruce, Stewart lampoons news media trends with a stream of wisecracks and a team of on-location correspondents whose buffoonery recalls the residents of Chelm, the fabled Jewish village of fools. Recently, for example, correspondent Stephen Colbert went to Maryland to interview homeowners who were being harassed by members of a gun club. “Why can’t you live peacefully with the firing range?” Colbert asked. “They live peacefully with you, er…except for all the shooting.”

Jon Stewart often refers to his Jewish identity on The Daily Show. He opened one show by saying, “I had a discussion with a Southern gentleman today, and we were trying to find common ground…about legalizing drugs. And he said to me, ‘I think ham should be legalized.’ And I said, ‘I think ham is legal. Now, I’m Jewish, when I eat it, I don’t feel so good about myself, but I eat it.’ And it turns out, he said, ‘Hemp.’ But in a way that made me say, ‘Ham.’ And I thought to myself, ‘So that’s how the Civil War started.’ It’s the misinterpretation.”

Stewart’s love of clever wordplay, a Jewish comedic tradition, also colors his prose fiction. Like many comics of the ’90s, he wrote a book of short humorous pieces. Released in 1998, his Naked Pictures of Famous People includes a number of pieces in which protagonists wrestle with their Jewish identity. In “Breakfast At Kennedys,” for example, a timid Jewish boy who has befriended the young John F. Kennedy in 1935 quietly endures the future president’s antisemitic abuse. In a sly, non-didactic way, this story exposes what historians have known for decades: though touted as a champion of the underdog, Kennedy, in his youth, was a spoiled brat who did not hesitate to make racist remarks.

Another comedy trend of the ’90s–“sick humor”–owes its inspiration to Lenny Bruce. Turning the tables on the politically-correct mindset of the ’90s, comedians like Dave Attell and radio “shock jocks” like Howard Stern–both Jewish–transformed taboo into titillation. Equal opportunity offenders, they smashed the sacred cows of the right and left wings with equal fervor. “Sometimes, for lack of a better word, people call [this comedy] ‘sick,'” says humor writer Tom Leopold, “but, in fact, it’s just so purely honest it’s hilarious, because it says what we all think, but can’t say. Lenny Bruce did that.”

Dave Attell, acclaimed by The New York Times magazine in 1994 as one of the thirty most brilliant artists under thirty, performs the “Ugly American” segments on The Daily Show with Jon Stewart and now writes and stars in a new Comedy Central series,Insomniac with Dave Attell–exactly the kind of television Lenny Bruce would have craved. Each thirty-minute show follows Attell as he enters America’s nocturnal world, populated by hookers, strippers, and junkies.

Comedy Central is also the home of South Park, an animated satire of small-town America from the perspective of a quartet of foul-mouthed children. Created in 1997 by Trey Parker (non-Jewish), and Matt Stone (Jewish), this “sick comedy” largely appeals to Generation X and their younger peers precisely because of its blunt satire of the hypocrisy employed by adults to achieve selfish ends. Stone, who writes many of the show’s scripts, is the voice of Kyle Broflovski, son of the only Jewish family in South Park. (His father wears a red kipah, and his mother is a typical yenta.) In a recent episode, Kyle questions the existence of God when he becomes deathly ill with hemorrhoids, while his cruel friend Eric Cartman (voiced by Trey Parker) inherits a million dollars and buys his own amusement park. In South Park Synagogue, Kyle stuns his best friend Stan Marsh (Trey Parker) with the following soliloquy:

“…All my life I was raised…to believe we should all behave a certain way, and good things would come to us. I make mistakes, but every week I try to better myself….And what does this so-called God give me in return? A hemorrhoid!”

To comfort Kyle, his parents tell him the story of Job, whose faith was similarly tested, but Kyle is unimpressed. By the end of the episode, however, Cartman loses all his money, and Kyle’s health–and faith–is restored. The lesson: the meek (and the faithful) will inherit the earth, while the Cartmans will fall victim to an unbending moral universe that does not tolerate evil. This is, in fact, the moral of many a South Park episode. Cartman, who represents evil incarnate, regularly schemes to victimize the more goodly residents of South Park; by the end of the episode, he ends up with nothing.

Another critically acclaimed Comedy Central show in the Lenny Bruce tradition is Robert Smigel’s TV Funhouse, a series of subversive animated shorts (for example, “The Ambiguously Gay Duo,” a homoerotic parody of Batman and Robin, was inspired by Bruce’s landmark adult cartoon “Thank You Masked Man,” which portrayed the Lone Ranger as gay). TV Funhouse comes in two versions–one on SNL and a second, even more outrageous one on Comedy Central, which shares the spot with a half-hour live action series delving into the sleazy behind-the-scenes antics of a children’s show and cartoons too racy for SNL. In one of these cartoons, an adorable yet antisemitic muppet named Mischievous Mitchell (a parody of Dennis the Menace) tricks his well-meaning non-Jewish neighbor Mr. Wilton into dressing like Hitler–then leaves poor Mr. Wilton to take the rap for the tasteless charade when his Jewish neighbors arrive on the scene. In an edgy, dark way, Mischievous Mitchell exposes the veiled pockets of antisemitism in America’s heartland.


“The Jewish concept of God is too difficult to fathom. An omniscient, omnipotent Peeping Tom who loves us and smites our enemies. Although recent history suggests he’s a little slow on the smiting.”

–from Naked Pictures of Famous People by Jon Stewart

The golden age of standup in the ’70s and the comedy club boom in the ’80s began to decline in the ’90s as audiences turned to cable TV for comic relief. Many standup comics quit the business, but those who were in it for the art, not the money, stuck around and honed their craft, helping to create an alternative comedy movement in the mid-’90s. New clubs, such as Rebar and the Luna Lounge in New York, featured Jewish comedians Marc Maron (Almost Famous, The Late Show with David Letterman), Sara Silverman (There’s Something About Mary), and Jeffrey Ross (Comedy Central Presents: The New York Friars Club Roasts), among others. In these alternative venues, comedians rarely performed rehearsed, “safe” TV routines. Sara Silverman, for example, once came onstage with fellow Jewish comedian Sam Seder dressed as Seder’s teenage nephew, a bar mitzvah boy who complains: “My friends don’t even know who you are! Adam Sandler is funny, and you are not funny! I wish that Adam Sandler was my uncle! You suck, and Adam Sandler rocks!” Industry bigwigs began flocking to these alternative spaces, hoping to cash in on what might become “the next big thing.” Silverman soon landed a spot writing and performing on Saturday Night Live, which led to film roles; Ross became a regular presence on Comedy Central; and Marc Maron’s one-man show, The Jerusalem Syndrome, enjoyed a sold-out Off Broadway run and, in 2001, was published as a book.

The more mainstream standup comedy clubs continued to headline Jewish comedians–including Susie Essman, Lewis Black, Hugh Fink, and Judy Gold–who were influenced by their counterparts in the alternative movement. Gone was the era of simple, Seinfeldian observational comedy. A new type of edgy, intellectual humor was on the rise, one that still made observations but also crossed the line into a more philosophic realm. Consider Hugh Fink’s “Pizza” joke: “I don’t like the way people are now using September 11th as an excuse. I was in Phoenix last week, and I ordered a pizza. I said, ‘Half pepperoni and half cheese.’ The guy came in half an hour later, and I said, ‘Hey, this is sausage. I said half pepperoni and half cheese.’ And he goes, ‘Um, due to the recent tragedy of September 11th, we forgot to put pepperonis on.'”

For Jewish women comedians, many of whom had encountered gender discrimination in the ’70s and ’80s, the playing field began to level out in the ’90s. “I’m treated more equally now,” says Susie Essman (Curb Your Enthusiasm, Dr. Katz, Professional Therapist). “My group of comedians–me, Judy Gold, Joy Behar–broke a lot of barriers. I took the discrimination as a challenge. I became so good that they couldn’t deny me–and now they don’t.” Like their male counterparts, Jewish female comics began incorporating more Jewish references into their acts, such as this recent Judy Gold routine:

“My mother just got an answering machine for her house: ‘You have reached 478-____. I live at 310 Gibson Boulevard. On Tuesdays from 8-11:30 I go to Bingo at the synagogue to help out. The money is in the top drawer of my dresser in the bedroom; the key is under the mat….'”


“Jake and I used to talk about how we needed to kick the dust off our faiths, bring ’em up to speed with the times. No more of the old routines. Jake said we’re gonna give ’em an old-world God with a new-age spin.”

–Father Brian Finn (Edward Norton), speaking about Rabbi Jake Schram (Ben Stiller), Keeping The Faith

The TV and film persona of Billy Crystal–funny, cute, and indelibly Jewish–helped pave the cinematic path for SNL comic and proud Jew Adam Sandler. But unlike the wisecracking Crystal, Sandler has shed the self-deprecating vaudeville and Borscht Belt humor of the past. As a result, he has been offered roles previously unavailable to Jewish men. He wrote and starred in Billy Madison (1995) and Happy Gilmore (1996), then tried his hand at films with more serous themes, such as 1998’s The Wedding Singer (about a struggling songwriter obsessed with marriage) and 1999’s Big Daddy (in which he’s forced to raise a small child). Later this year, Sandler’s most explicitly Jewish film will be released–Adam Sandler’s 8 Crazy Nights (taken from a line in his “Hanukkah Song”). This animated musical starring Sandler, as well as Jewish SNL alumni Jon Lovitz and Rob Schneider, tells the unlikely story of an aging coach who teams up with the head of marketing for the New York Knicks to coach a basketball team. The film is set to premiere in time for Hanukkah 2002.

Another writer/performer who is also filling these new “cool” Jewish shoes is Sandler’s pal Ben Stiller (they appeared together in Happy Gilmore). The son of Jewish comedians Jerry Stiller (born Jewish) and Anne Meara (a convert to Judaism), Stiller has played a number of openly Jewish roles in feature films. In the 1998 drama Permanent Midnight, he starred as the heroin-addicted Jewish comedy writer Jerry Stahl (Alf, Moonlighting), on whose life the film is based. In Keeping The Faith (2000), written and co-produced by Jewish writer Stuart Blumberg, Stiller plays Rabbi Jacob “Jake” Schram, a hip, handsome, charismatic Jewish spiritual leader who sports leather jackets and dark sunglasses and remains devoted to both his rabbinic duties and his mother. But the rabbi has a problem–he has fallen in love with a non-Jewish woman. To complicate matters, his close friend Father Brian Kilkenny Finn (Edward Norton) has also fallen for Anna Reilly (Jenna Elfman), their childhood friend who works as a high-powered corporate troubleshooter. The film stresses that an interfaith relationship is an issue of contention among Jews, just as celibacy is controversial among Catholics. After much turmoil, Rabbi Jake wins Anna’s affections and resolves to bare his soul to the congregation. He confesses in his Yom Kippur sermon: “Over the past few months, I have been violating [your] trust…because I haven’t been sharing my life with you….I’ve been seeing a woman who isn’t Jewish….Tonight, I stand before you and ask you to forgive me.” At the end, he realizes that the relationship might work after all–Anna has been studying with his mentor, Rabbi Lewis (Eli Wallach), and might convert. Ben Stiller’s portrayal of Rabbi Jake as a “cool” rabbi is a watershed event: it’s the first time a rabbi has been depicted in mainstream American cinema as hip, fashionable, attractive, and, perhaps most importantly, as a romantic lead.

Jewish comedy writers and performers have made great strides since World War II, advancing from self-caricature to self-confidence. Blessed with their “outsider” vantage point, street-smart creativity, and outsized chutzpah, they have pushed the boundaries of comedy to the outer limits, compelling audiences to confront persistent prejudices and question received truths. The current level of mainstream acceptance they have achieved says as much about America as about the art of making people laugh.

Arie Kaplan is a freelance writer who has written for MAD magazine, Entertainment Weekly, and Time Out New York, among other publications. He has also written jokes forMTV’s Total Request Live. Illustration by Fred Harper.


Richard Lewis: 
“My family wasn’t very religious. On Hanukkah they had a menorah on a dimmer.”

Jon Stewart: 
“I celebrated Thanksgiving in an old-fashioned way. I invited everyone in my neighborhood to my house, we had an enormous feast, and then I killed them and took their land.”

Rita Rudner: 
“Why are women wearing perfumes that smell like flowers to attract men? Men don’t like flowers. I wear a scent called ‘new-car interior.'”

David Steinberg: 
“Fortunately, my parents were intelligent, enlightened people. They accepted me exactly for what I was: a punishment from God.”

Jackie Mason: 
“My grandfather always said, ‘Don’t watch your money; watch your health.’ So one day while I was watching my health, someone stole all my money. It was my grandfather.”

Jonathan Katz 
“My dad called me up the other night, very excited. He said, ‘Jonathan, when I get up to go to the bathroom in the middle of the night, I don’t have to turn on the light, the light goes on automatically. When I’m done, the light goes off automatically.’ I said, ‘Dad, you’re peeing in the fridge, and it’s got to stop.'”

Jerry Seinfeld: 
“I once had a leather jacket that got ruined in the rain. Why does moisture ruin leather? Aren’t cows outside a lot of the time?”

Gilbert Gottfried: 
“I went up to Jackie Kennedy at a party and figured I’d try to break the ice by getting a little conversation going. So I said, ‘Do you remember where you were and what you were doing when you heard that Kennedy was shot?'”


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