Jon Stewart, Louis C.K., Chris Rock, Stephen Colbert, Conan O'Brien and the behind-the-scenes secrets of comedy's '90s glory days

Before they were famous, today's brilliant comics toiled on "SNL" or elsewhere -- and despaired of making it big

Published November 24, 2015 12:00AM (EST)

Jon Stewart, Louis CK, Chris Rock, Conan O'Brien   (AP/Reuters/Salon)
Jon Stewart, Louis CK, Chris Rock, Conan O'Brien (AP/Reuters/Salon)


The hack comedians of the Comedy Boom abandoned their Jack Nicholson impressions and returned to their former lives. Creative comedians who kept at it emerged as the top comedy stars of the new millennium. Mainstream comedy was in a slump, but two ancillary scenes—the Alternative Comedy world and a new genre of predominant African American comedy—created some giants.

Eddie Murphy’s monumental success in the 1980s inspired a new generation of Black comics to enter the game. It created a parallel stand-up scene that flourished in the early 1990s while white comedy clubs were imploding. “Before I came out you had Richard [Pryor] and Bill Cosby and Flip Wilson and Redd Foxx and a handful of people,” said Murphy. “After I came out it was just a fucking explosion of comics. Because I was so young it made the art form accessible to a lot of people.”

Eddie Murphy was arguably the biggest comedy star of the 1980s. Stand-up, television, records and movies—he was dominant in every genre. His concert films Raw and Delirious inspired untold numbers of African American youth to try stand-up, and by the early 1990s they were seasoned professionals. While stand-up programming of the Boom era disappeared from television, new shows geared specifically to an African American demographic were successful. Eddie Murphy had created an entire movement.

“Eddie was the biggest star,” said Chris Rock. “Anybody who says different is making a racist argument. Eddie Murphy has the biggest numbers in the history of movies. Grosses are people; it’s not dollars marching in, those are people.”

Murphy was Chris Rock’s earliest champion, altering his life on a chance night at the Comic Strip in New York. “I just came in, like I always did, not on the schedule, just to hang out,” said Rock. “I remember a bunch of Porsches and great cars out front. I come in and they say, ‘Eddie Murphy’s here.’ Eddie wanted to see a black comic. I was the only one around so they put me up. And it was a Friday night, prime time, and the place was packed. I had never been onstage in front of more than like twelve people or whatever, and here the place was filled, and I went on in front of Eddie Murphy and I did great. Eddie liked it and I knew that because you could hear that distinctive laugh of his all through the room.”

At the time Chris Rock’s act sounded a lot like Henny Youngman:

My father is so cheap when we go to bed he unplugs the clocks.

Murphy loved him and told Rock to phone him on the weekend. Murphy invited Rock to join him for a screening of the Spike Lee film She’s Gotta Have It. “This whole thing happened really, really quick. I met Eddie on a Friday, went to the movies that Sunday . . . after the movie Eddie says to me, ‘We’re going to L.A. tomorrow so if you wanna come, just come.’ I had never been on a plane before, certainly never went to L.A. before, and never stayed at a hotel before. Eddie was doing re-shoots for The Golden Child. Eddie Murphy took me out to L.A. and was putting me in his movie.”

Rock was part of Saturday Night Live by 1990. At the same time Fox, HBO and Showtime started using several Black comedians for sketch, sitcom and stand-up programming. Three shows in particular—Showtime at the Apollo, Def Comedy Jam and In Living Color—buoyed what was turning into a Black comedy boom.

Keenen Ivory Wayans and his brother Marlon had been stand-up mainstays at the Improv in New York when they sold their sketch series to Fox. In Living Color was the first Black-oriented sketch series in television history. Jim Carrey was its sole white cast member, Larry Wilmore was one of its writers and it got attention from important people. Jonathan Winters said, “To me one of the funniest shows that went way out was In Living Color with the Wayans Brothers and Jim Carrey.”

Rock was frustrated watching Black performers with so much screen time while he was stuck with little to do on SNL. “The black comedy boom was happening and I wasn’t part of it. In Living Color was a big show and Def Comedy Jam was on HBO and Martin Lawrence was on. So there was all this stuff happening and I was over here in this weird world, this weird, Waspy world.” Rock left SNL in 1993 and joined In Living Color. Ironically, it was on the Black-centric program on which he was able to do comedy not about race. “On SNL, I either had to play a militant or a hip-hop guy. Living Color allowed me to talk about other shit.”

Def Comedy Jam premiered on HBO July 1, 1992, and ran five years. It was by far HBO’s most successful comedy program. The critical favorite on HBO was The Larry Sanders Show, starring Garry Shandling, Jeffrey Tambor and Rip Torn. And although Shandling’s program gave early jobs to Judd Apatow, Todd Barry, Janeane Garofalo, Mary Lynn Rajskub, Bob Odenkirk, Jeremy Piven, Sarah Silverman and Jon Stewart, its ratings were below expectations. Brillstein-Grey producer Kevin Reilly said, “I used to get the numbers every week and Def Comedy Jam had like four times the ratings of Larry Sanders.”

Def Comedy Jam was an offshoot of Russell Simmons’s enormously successful Def Jam Recordings. “Russell always had a love of comedy and he would frequent comedy clubs,” said the program’s talent coordinator, Bob Sumner. “When it was mentioned that an African American comedy series might be cool everybody was in agreement to do it. I took some executives from HBO around to some comedy clubs and they could see black comedy was really popping. Then they allowed us to do a pilot. That pilot turned into eighty-two shows.”

Def Jam had several hosts, but its first—Martin Lawrence—was the breakout star. On the heels of In Living Color’s success, the Fox network cranked out more African American talent than any other channel in television history, before or since. Martin Lawrence was the cornerstone from which Fox built its succession of Black sitcoms, and the network used Def Comedy Jam as its casting call.

Down the ladder in terms of quality, but almost as successful, was the BET channel’s Comic View. This stand-up program, originally hosted by D. L. Hughley, endured despite its frequently amateurish approach. Hughley was a cut above the guests, but he had a reputation along the Black stand-up circuit as a joke thief and he bothered BET executives with his on-air cussing. BET replaced him with Cedric the Entertainer, who accepted the gig despite being warned against it. “A lot of my contemporaries were telling me not to do BET,” said Cedric. “They were telling me that doing Comic View for me would have been a step in the wrong direction. They wanted me to wait and do my material on the next season of Def Comedy Jam. Comic View was a nightly show back then. It came on five nights a week, so I knew it would give a lot of boost to my career. It was a great run. It put me on the map.”

As with the shows Make Me Laugh and Star Search that came before, many comedians decided frequent exposure on Comic View was more important than the actual quality of the show. It boosted the drawing power and income of many of them when they took to the road.

The frequent airing of Comic View created an insatiable need for new comics, and the program often used comedians who weren’t television-ready. “Comic View threw on every comic that submitted a tape in ’98,” said Darryl Littleton, author of Black Comedians on Black Comedy. “If it turned out that they weren’t funny, the production staff dubbed in cricket sounds and showed an impassive audience staring at the performer in a state of disgust with a nasty phrase encased in a comic strip bubble inserted above the comedian’s head.” Comic View lasted a remarkable eight years, longer than any other entity of the Black comedy boom.


White comics, even those who were established, struggled to sustain themselves with stand-up gigs alone in the early 1990s. Louis C.K., Jon Stewart and many others started writing for television to cover their expenses.

Jon Stewart entered the business during the height of the Comedy Boom. His first gig in front of a live audience was working “disabled puppets” in an ensemble called the Kids on the Block. The group played school assemblies in an attempt to teach children empathy. Stewart said he operated “a cerebral-palsy puppet, a blind puppet, a deaf puppet, a hyperactive puppet—and a puppet who couldn’t commit to a relationship.”

He did his first stand-up gig at the legendary Bitter End, still a historic but no longer great comedy venue. Bitter End manager Paul Colby said Stewart “bombed atomically. It was terrible to watch.” Nearby was the Comedy Cellar, the club later made famous by the FX series Louie. Stewart made it his homeroom. “I went on for two years at the Comedy Cellar at 2:30 or 3 A.M. as the last guy. It was me and the waitstaff and a table of drunken Dutch sailors. And in that place, I learned how to be myself.”

His gigs improved. Stewart opened for veteran comedian Alan King, warmed up the crowd for a Showtime special and was Sheena Easton’s opening act in Las Vegas. In 1989 he joined fellow comedians as a staff writer on Caroline’s Comedy Hour, the four-season A&E stand-up program. It resembled most Boom-era stand-up shows, distinguished only by its scripted, interstitial sketches. Michael Patrick King, the writer who later shaped Sex in the City, oversaw the sketches. King assembled an impressive staff and at one point the writers room included Jon Stewart, Dave Attell, Susie Essman, Colin Quinn and Louis C.K.

When the show was canceled in 1993, King moved to the fledgling Comedy Central and brought Stewart along to write some of the flagship programs. Stewart was soon named host of the low-budget Short Attention Span Theater, a show that utilized old comedy footage from the Viacom library. That led to a hosting gig on a cheap MTV program. (Comedy Central replaced Stewart with comedy’s future podcast champion, Marc Maron.)

In March 1993 Stewart was booked as a stand-up on Late Night with David Letterman. Stewart was the last of many comic stars to get a break from Letterman’s NBC show before its run ended. Letterman’s production company expressed interest in Stewart, and because of that MTV started treating him more seriously and green-lit Stewart’s idea for a talk show.

The Jon Stewart Show premiered on MTV on October 25, 1993, and it was soon second only to Beavis and Butt-Head in channel popularity. A few months later, when comedian Arsenio Hall announced he was leaving his syndicated talk show, the Stewart program was revamped for syndication, expanded to an hour and hustled in Arsenio’s former markets. Comic Howard Feller was the sidekick on The Jon Stewart Show. “Jon Stewart was seen as this rising star and was doing fairly well on MTV. Arsenio Hall left. They needed a replacement, but a lot of the African American audience loyal to Arsenio wasn’t going to watch Jon Stewart. It didn’t get the black audience, although it probably would have if not for us replacing Arsenio. It almost looked like Jon Stewart kicked Arsenio off the air.”

Stewart’s writing staff at various points included comedians Dave Attell and David Cross and former Comedy Channel hosts Dave and Steve Higgins. Airing four nights a week for nine months, the program was frequently described in the press as a talk show for Generation X. When it was canceled on June 23, 1995, and a newbie named Conan O’Brien remained on the air over on NBC, critical backlash said it should have been the other way around.

New York magazine ran an article titled “The Man Who Should Be Conan” and chronicled Stewart’s cancellation: “Stewart staff members, busy boxing up their belongings, blamed the cancellation on everything from lame promotional support by the show’s syndicator . . . to the inevitable internal debates about whether Stewart should be a talk show with comedy sketches or a comedy show with talk, to Stewart’s coming across as just too damn nice.” Rumors speculated that Stewart would move to one of the major networks, but in the end they proved wrong. He figured his career was over. “I’m compiling rationalizations now,” said Stewart. “It’s hard not to take it as a personal rejection. I was looking for a hug—and America spit in my face.”

From the ashes of the Comedy Boom came a DIY scene on both coasts, a new forum for comedians with a creative impulse. Alternative Comedy was an early 1990s antidote to the brick-wall conformity symbolizing stand-up in the 1980s. Innovative television like The Larry Sanders Show, Late Night with Conan O’Brien, The Ben Stiller Show, The Dana Carvey Show and Mr. Show was cast from the ranks of the Alternative Comedy scene.

The phrase “Alternative Comedy” was an offshoot of the 1990s record store category “Alternative Music,” the catchall under which you’d find Nirvana and Pearl Jam cassettes. The difference between alternative comics and regular stand-up comedians usually had to do with the venues where they performed—alternatives to commercial comedy clubs.

“You would go to the Improv, which was, supposedly, a place you could work on material,” says comic Dana Gould. “But every night Jim McCawley from The Tonight Show was there or the president of show business was there. You couldn’t work on stuff because if they saw you bomb they thought, ‘Oh, he’s not very funny.’ We wanted a place where you could go and bomb, a place to do new material. There was a real cool place on Beverly Boulevard called the Big and Tall Books. It had a loft, a little upstairs room, that seated forty people. We started to do shows there and devised a thing where you couldn’t do material you’d already done—everything had to be new. It was a magical time—like when the grunge scene came together in Seattle. A bunch of things coalesced, a lot of great comedians: Andy Kindler, Janeane Garofalo, Bob Odenkirk, David Cross, Patton Oswalt, Julia Sweeney, Taylor Negron, Andy Dick. Beth Lapides would book the show and it became the cool night out.” Surrounded by the alternative literature that defined the decade, like Peter Bagge’s Hate, Alternative Comedy became a legitimate genre that attracted a cerebral audience.

Ben Stiller was the son of comedy team Stiller & Meara. Anne Meara and Jerry Stiller played the hip Village venues of the 1950s and 1960s as part of the New Wave comedy scene. Now, thirty years later, Ben Stiller was part of the like-minded Alternative Comedy world. “I met Ben Stiller through Janeane Garofalo in New York,” says Gould. “Then Ben moved to Los Angeles and I introduced him to Judd Apatow. Janeane knew Bob Odenkirk. Judd knew Andy Dick. It was a social group.”

Judd Apatow was contributing material to the stand-up acts of Jim Carrey, Garry Shandling and Roseanne while performing his own material on shows like An Evening at the Improv. “I used to tour a little bit with Jim Carrey. I wrote for Roseanne—wrote her stand-up act with her. I would take brief gigs here and there.” After Gould introduced them, Apatow and Stiller started to collaborate. They sold comedy sketches that MTV aired between music videos, and that led to a deal with Fox for The Ben Stiller Show. It signaled the end of Apatow’s stand-up career and the start of his life as a writer-producer. “When The Ben Stiller Show was picked up, I realized there was no way for me to do stand-up three or four nights a week and run this television show with Ben. So that was the moment.” The program had a cult following during its only season and was the first steady TV gig for Andy Dick, Janeane Garofalo and Bob Odenkirk. As with David Letterman’s morning show ten years before, it won an Emmy after cancellation.


Bob Odenkirk was shepherded into professional showbiz by Robert Smigel, a key Saturday Night Live writer best known today for his caustic puppet Triumph the Insult Comic Dog. In 1985 Smigel was hired with future Kids in the Hall members Bruce McCulloch and Mark McKinney to write on SNL. It was an impressive writers room that included Al Franken, Tom Davis, A. Whitney Brown, Jim Downey, Jack Handey, Carol Leifer, George Meyer, Don Novello, Herb Sargent and John Swartzwelder. Within two years Smigel was upstaging most of them. “He wrote a lot of sketches that were definitive for our time, for our generation,” said Odenkirk. “The Star Trek sketch from 1986, in which William Shatner tells the Trekkies to ‘get a life.’ ‘Da Bears’ was his idea. He gave that show the strongest and smartest sketches that it had for a couple of years.”

Odenkirk was working at Second City and fed Smigel ideas by proxy. “I would sort of work with him on the phone every week and pitch him ideas . . . sometimes they would do a joke of mine on Weekend Update. I came in and did an interview the following year, which was Robert’s second year. I was hired a few months later.”

SNL hired the writing team of Greg Daniels and Conan O’Brien for the 1987–1988 season, but that spring a Writers Guild strike brought the program to a halt. With nothing to do, Smigel and Odenkirk returned to Chicago, where the comedy scene was nurturing talents like Steve Carell, Stephen Colbert, Chris Farley, Jeff Garlin, Jane Lynch, Andy Richter and Amy Sedaris. “Bob and I decided to go back to Chicago and do a sketch show together,” says Smigel. “We invited Conan to do it with us. Some famous sketches came out of that show, including ‘Bill Swerski’s Super Fans’ and ‘In the Year 2000.’” The latter became one of the signature segments on Late Night with Conan O’Brien. SNL returned the following season and won an Emmy. Robert Smigel, Bob Odenkirk and Conan O’Brien had their names on an Emmy Award—long before anyone had ever heard of them.


Late Night with Conan O’Brien was born out of a network crisis. Johnny Carson’s retirement in 1992 and the battle between Jay Leno and David Letterman was big news, chronicled in detail by journalist Bill Carter in his book The Late Shift. When Letterman fled to CBS it left a vacancy in NBC’s post–Tonight Show time slot. NBC needed to appease advertisers and affiliates across the country.

The affiliates were pleased with Saturday Night Live, which had become a very profitable franchise. The success of a film based on one of its sketches, Wayne’s World, made Lorne Michaels a powerful mogul. When it came time to fill the post-Letterman void, NBC looked to Michaels for guidance.

“They had to sell the late night time slot to their affiliates before they were able to put a show in place,” says comedian Paul Provenza. “They didn’t have anything—they just had the time slot. So their idea was to make a deal with Lorne Michaels and make him the star of the time slot for the buyers.”

Conan O’Brien was by then writing on The Simpsons and punching up the screenplay for So I Married an Axe Murderer. He heard about the opening before anyone else. His sister tipped him off. “I was working at William Morris,” said Jane O’Brien. “[I] had access to the confidential e-mail when it was announced that Lorne Michaels was given the Late Night time slot. I called Conan and told him. I just knew it was his.”

NBC president Warren Littlefield wanted comedian Garry Shandling for the job. Late Night with Garry Shandling looked like it might happen, and Michaels even asked O’Brien to produce it. “I wasn’t interested,” said O’Brien. “I did not think, ‘No! Not Garry Shandling. Me!’ But I told Lorne I wanted more performance.” In reality, Shandling didn’t even want the job, but used the offer to frighten HBO into implementing demands he had regarding The Larry Sanders Show.

Shandling gone, others tested for the job. Dana Carvey, Drew Carey, Michael McKean, Paul Provenza, comedian Rick Reynolds (whose stand-up special on Showtime had just got an Emmy nod), Ray Romano, Jon Stewart and O’Brien all auditioned. Using the Tonight Show set in Burbank, they were required to do a mock interview for NBC executives. NBC asked Jay Leno for his input, and he leaned toward Provenza, who was doing a talk show on Comedy Central called Comics Only. Provenza says, “NBC was holding out for me. Lorne Michaels was really offended that NBC used Jay Leno as a consultant. Because of that there was no fucking way anyone Jay suggested would get signed.”

Dana Carvey became the front-runner. “Lorne wanted Dana to do it,” says Robert Smigel. “Dana talked to me about it. Carvey knew how much I loved to work with Conan. He said, ‘Yeah, you guys could both be featured players!’ I immediately formed a lot of ideas. I pictured a late night sketch comedy show with characters and guests—and guests who were characters.” Carvey ultimately changed his mind, deciding the grind would be too stressful and time-consuming.

Lorne Michaels used his persuasive powers, and NBC went with the least experienced candidate: Conan O’Brien. Smigel desperately wanted to be part of the project. “I weaseled my way into doing the show with him. I was one of the senior writers at SNL and Lorne didn’t want me to go. To me, it was a dream. I knew who Pat Weaver was and I cared about that kind of thing. My dream was creating the show. Conan’s dream was hosting the show.”

Michaels had O’Brien tape two weeks of practice shows to assure NBC it wouldn’t be a disaster, while Smigel went through the process of assembling a staff. Comedian Jeff Garlin recommended Andy Richter, whom Smigel knew through Chicago sketch comic Beth Cahill. O’Brien and Richter met at Canter’s Delicatessen in Los Angeles, and their chemistry was immediate. Jeff Garlin further recommended Louis C.K. “We watched Louis’s stand-up and watched two of his short films,” says Smigel. “Jeff Garlin recommended him and [comedian-writer] Dino Stamatopoulos pushed hard for him, so Conan and I went with it.”

Louis C.K. was reeling from the implosion of the Comedy Boom at the time. “I was going broke. I was just devastated. I wasn’t making a living. I remember calling Marc Maron, who was living in San Francisco. I was up until dawn talking to him on the phone. I was so fucking depressed. And then I got a phone call out of nowhere from Robert Smigel. He said, ‘I’d like to take a chance on you. I’m writing for Conan.’ I didn’t even know what that was.”

Michaels sent Smigel on a scouting mission to Second City, in particular to check out the buzz surrounding a kid named Steve Carell. “We went to a Second City show and Steve Carell wasn’t even there that day,” says Smigel. “There was an understudy doing his part. I thought, ‘Oh, well.’ I saw the show and I thought the understudy was hilarious! The understudy was Stephen Colbert.”

Smigel arranged a meeting with O’Brien and Colbert, expecting the same chemistry he’d enjoyed with Andy Richter. “I wanted him to meet Colbert. It was just the three of us at a bar, but there wasn’t anything comfortable about it like when he met Andy.” Colbert said, “We met at a bar, had a couple of beers, talked. I submitted some jokes—and didn’t get hired.”

Late Night with Conan O’Brien premiered on February 13, 1993, and Louis C.K. quickly put his stamp on it, creating recurring pieces that were used for years. “Louis was the most prolific and probably the best writer on the show,” says Smigel. “I created a fair amount, but Louis created more than anyone. He created bits that were done for years, like ‘Actual Items,’ ‘Staring Contest,’ ‘Bad Fruit Theater’ and ‘Patterns.’ He was super-strong.”

Smigel created a signature bit that was done the first week on the air. O’Brien conducted phony “via-satellite” interviews with people like President Clinton, in reality a photo with Smigel’s human lips superimposed over the mouth, a takeoff on the low-budget Clutch Cargo cartoon of the 1960s. “We did the Clutch Cargo bit on the second show. The audience laughed so hard—it was such a thrill. Everything I wanted was happening. We were doing something different from any other talk show.”

The program’s comedy was decidedly weird. While the people responsible for it would become critical favorites in another fifteen years, reporters at the time were dumbfounded. They dismissed Late Night with Conan O’Brien as a lousy Letterman knockoff and dismissed O’Brien as an inept personality. Rick DuBrow at the Los Angeles Times wrote, “In the wee hours after Letterman and Leno, NBC’s new Conan O’Brien series was an awkward, fumbling yawn.” Tom Shales at The Washington Post wrote, “O’Brien’s show just lies there, as lifeless and as messy as road kill.” TV Guide said, “[Conan is] a twitching frat boy who thinks he’s much cuter and funnier than he actually is.” The bad press affected the studio audience itself. “December 1993, our first winter, was the worst time I will ever have,” said O’Brien. “I’d go out to do the warm-up and the back two rows of seats would be empty.”

Late Night with Conan O’Brien remained on the air against all odds, a testament to the power of Lorne Michaels. Critics did not let up. “They hated it the whole time I was there,” said Louis C.K. “We just fought to stay on the air, constantly faced with extinction. Every Friday the word would come, ‘This is probably our last week,’ and everybody would call their agents.”

New hires were signed to hesitant thirteen-week contracts and writers quietly inquired about other gigs. Louis C.K. continued to do stand-up. “We’d be there until three in the morning working something out. So I’d literally say, ‘I’m gonna go to the bathroom,’ and I’d go downstairs, hop on my motorcycle, run to the Comedy Cellar and do a set, then come back and try and play it off like I took a big shit.” Late Night with Conan O’Brien cast many of its sketches using people out of the Upright Citizens Brigade, a new sketch collective that was considered hipper than its precursors. Founded by Amy Poehler, Ian Roberts, Matt Walsh and Matt Besser in Chicago in 1991, it acted as an alternative to Second City, which was by then touting itself as a tourist destination. “We had no respect for any other comedy enterprise in Chicago,” said UCB member Horatio Sanz. When the collective moved to New York in 1996, members started to show up with regularity on The Daily Show and Late Night with Conan O’Brien. “They were like a repertory company for us,” says Late Night with Conan O’Brien writer Brian Stack. “The first sketch I wrote at Conan was called ‘Andy’s Little Sister,’ and Amy Poehler starred in it.”

While critics complained about Late Night with Conan O’Brien, David Letterman was impressed. He told the staff, “The more I watch the show, I realize you guys do an incredible amount of comedy, and the stuff that is produced is at a very high level. The volume and quality of the stuff just knocks me out.”

So much so that Letterman wanted Louis C.K. for his own. “I was trying to get on Letterman as a comic,” said C.K. “My manager approached Letterman’s show for the fiftieth time. They said, ‘Would he write here? ’Cause that would really make us interested.’ And we said only if I could do stand-up. I didn’t want to write on Letterman. I hadn’t even been on the show yet and I’m meeting David Letterman. He said, ‘Look, I saw your Conan reel. You’re really, really great. We really feel like this show needs to go somewhere new. So the idea of having you come here and shaking things up is exciting to me. So will you write for me?’ He just asked me point-blank. And I just said, ‘Yeah.’ What am I gonna do? And it was a miserable three months. I had a rotten time there. So I quit.”


Meanwhile Smigel left Conan to write a “Da Bears” screenplay with Bob Odenkirk. It was commissioned by Paramount, but the studio shelved the project. Dana Carvey was going through an equally frustrating period. After having passed on his late night opportunities, his intention was to make quality comedy films, but those hopes were quickly dashed by studio interference. Carvey recalled, “After these horrible movie experiences I said, ‘Oh, man, I really would love to do something with Smigel, who I enjoyed so much. Maybe we’ll do a variety show somewhere.’”

Carvey, C.K. and Smigel joined forces and devised a sketch comedy program. “I had really wanted to do it on cable, HBO,” said Carvey. “Robert and other people really believed, ‘You have the face for prime time. You should be with a big audience.’” In order to cast The Dana Carvey Show, Smigel acquired the rejected audition tapes from Saturday Night Live and went through them. Among the people he looked at were Jimmy Fallon, Ana Gasteyer and Tracy Morgan.

Out of the tapes only comedian Jon Glaser was hired, as his weird sensibility seemed to fit. “My celebrity impression was the head coach of the Detroit Lions and my political impression was King Hussein of Jordan,” says Glaser. “I didn’t get SNL, but Robert Smigel liked my King Hussein and told me he wanted me to do it for The Dana Carvey Show.”

At Second City, Stephen Colbert had been Steve Carell’s understudy and Jon Glaser had been Stephen Colbert’s understudy. Smigel hired all three of them.

Adding to the roll call of future giants was a taciturn writer named Charlie Kaufman. It was the first job for the man who went on to write Being John Malkovich, Adaptation and Eternal Sunshine of the Spotless Mind. “His writing submission was not fantastic,” said Smigel. “[It] was up and down, but kind of interesting. There was one sketch that was a very meta treatment of Unsolved Mysteries. It was one of the most brilliant sketches I had ever read, and it was enough for me to hire him.”

With future giants like Louis C.K., Stephen Colbert, Steve Carell and Charlie Kaufman all involved, how could it miss? The Dana Carvey Show premiered on ABC on March 12, 1996. Within seven weeks it was canceled.

The Dana Carvey Show had Tim Allen’s high-rated sitcom Home Improvement as its lead-in. For anyone else this would have been an asset, but unfortunately these two programs had completely different temperaments. The Dana Carvey Show was on Disney-owned ABC, but its approach was more in line with Carvey’s initial HBO ambitions.

The very first sketch of the series featured Carvey playing President Bill Clinton, telling the American people he “felt their pain” as the “compassionate president” and would nurture them. He then opened his shirt, exposing six nipples and breast-feeding a litter of kittens. “The president breast-feeding was probably the worst decision I’ve ever been involved in,” said Smigel. “It was Louis C.K.’s idea. I foolishly got very excited about it, and Louis even said, ‘You know what’s great about this? We’ll be able to really draw a line in the sand for people. Are you with us or aren’t you?’ For some insane reason, just a purely naïve moment of thinking about nothing but making myself laugh, I agreed with him. I was so stupid. I didn’t even watch Home Improvement. I should’ve taken a second to watch five minutes of it. I’d heard Tim Allen had done coke and gone to jail. Then, about five shows into it, after a horrendous ratings drop-off, with every week getting worse and worse, I finally tuned in to Home Improvement. I was absolutely mortified. Not just for myself, but for the audience to whom I’d subjected The Dana Carvey Show.”

Louis C.K. lamented that it was an “amazing pool of talent and we just couldn’t turn it into anything. And the network hated us. I was so depressed.”

Excerpted from "THE COMEDIANS: DRUNKS, THIEVES, SCOUNDRELS AND THE HISTORY OF AMERICAN COMEDY." Copyright © 2015 by Kliph Nesteroff; reprinted with the permission of the publisher, Grove Press. All rights reserved.

By Kliph Nesteroff

Kliph Nesteroff is a former stand-up comic turned writer. A longtime contributor to WFMU, writing about the history of comedy, Nesteroff’s latest project is hosting the Classic Showbiz Talk Show, a live series in Los Angeles that has welcomed comedy luminaries like Mel Brooks, Fred Willard and Laugh-In creator George Schlatter. He tweets at @classicshowbiz.

MORE FROM Kliph Nesteroff