“My vision of hell is a bunch of monitors with my old shows running on them,” Kimmel told Vulture.

Now Kimmel has gotten a sense of what hell might feel like after blackface impersonations he did of celebrities like Oprah Winfrey and Karl Malone on The Man Show resurfaced in June. “I have long been reluctant to address this,” Kimmel began his apology in a statement obtained by CNN on Tuesday. But rather than focus on the racism of his sketches, referring to makeup artists tasked with making him “look as much like Karl Malone as possible,” Kimmel seems to focus on how these past sketches have been weaponized to specifically hurt his recently built brand of a progressive-leaning television host. “Looking back, many of these sketches are embarrassing, and it is frustrating that these thoughtless moments have become a weapon used by some to diminish my criticisms of social and other injustices,” he said.

“I love this country too much to allow that,” he continued. “I won’t be bullied into silence by those who feign outrage to advance their oppressive and genuinely racist agendas.”

For Kimmel, his blackface impersonations and the frat boy degradation that made The Man Show a hit are just an embarrassing aspect of his past, a blip of immaturity in a career that has since been reformed by his show Jimmy Kimmel Live! and gigs like hosting the Oscars. In recent years, Kimmel has been outspoken about healthcare reform in America and has called out President Trump on his late-night show. But The Man Show—both its racism and sexism—laid the foundation for his current, high profile success. It’s also the reason why viewers, comforted by the reassuring political centrism of late-night television, continue to consider Kimmel an authority.

Kimmel officially broke into television in the late 1990s as the host for Win Ben Stein’s Money, the only game-show on Comedy Central in 1999, after previously working in radio as a sports reporter for Los Angeles’s KROQ. On the show, contestants played against the droll conservative speechwriter turned actor, Ben Stein, answering general trivia questions to win a portion of Stein’s paycheck. And while Kimmel wasn’t the star of the show—Stein was center stage, antagonizing contestants and answering questions—he honed his early comic voice as a TV host. “Did some kind of homo bomb explode backstage?” he asked one episode, remarking on how multiple contestants in one episode were gay.

Win Ben Stein’s Money was a success for Comedy Central, winning six Daytime Emmy awards, and the network continued to bank on Kimmel as a starring host. In 1999, the network debuted the Kimmel-created Man Show, billed as a guy’s program for guys, like a talk show with Hooters-like branding. Beer flowed freely, and women, known as “The Juggy Dance Squad,” ran through the audience, pausing for careful close-ups of their breasts. In their rolling on the street segment, the show sent out its “Man Show Boy,” an actual child, to ask grown women on the street if they’d have sex with him. Meanwhile, Carolla and Kimmel described the show as a truth-speaking “dam to hold back the feminization that is flooding this country” and a “dam to stop the river of estrogen that is drowning us in political correctness.”

Fighting the good fight against political correctness, the show continually criticized Oprah for “brainwashing” women, calling her a “money-grubbing pig.” And Kimmel complained about his now ex-wife Gina frequently. “Is it so much to ask for you to churn a little butter every once in a while?” he says one episode. “Just a few areas I’d like you to look at, jiggle butt, nothing major, we’ll get them taken care of.” Later, Kimmel goes through his wife’s bathroom cabinets to find out what takes her so long to get ready and points to a loofah. “This is supposed to get cellulite off your ass and thighs,” he notes.

The show was a hit and found an immediate audience, especially among men who welcomed a male viewpoint they perceived as being silenced by network television. At the time of its release, The Man Show entered an entertainment industry crowded with popular movies and TV shows that celebrated unbridled masculinity, from dramas like Office Space and Fight Club to comedic fares like American Pie and the MTV prank show Jackass. The Man Show had the shock jock spirit of a radio show like Howard Stern and the goofy immaturity of Adam Sandler movies like Billy Madison, so it’s no surprise that the show found an eager audience ready to lap up its frat boy schtick. “In today’s politically correct society, it’s refreshing to see someone who’s not afraid to be himself and champion the cause of enjoying what men like to do—with tongue firmly in cheek,” wrote Bob Barnes for the website BeerDude.com in an interview with Kimmel.

Kimmel, who also served as head writer for 77 episodes, embraced his Man Show personae in interviews. “I think as a group men are smarter than women, of course, and I will defend that to my death,” Kimmel said in an interview with NYTV in the show’s early days. “There’s a reason why men are in charge of the world and they have been since humans were here, and it’s because we’re just a little more clever than the female of our species.” The excessive, dopey masculinity of the show, the harping on “bitching and moaning women,” led critics to question if Kimmel and Carolla were playing off these stereotypes as satire, or earnestly embodying them. “The Man Show stops being funny once you realize that’s the whole joke,” Variety wrote in 1999.

But it didn’t matter whether or not the two were engaging a self-consciously snickering critique of misogyny, because the show plainly reaped the benefits of its messaging. The Man Show was immediately popular, reportedly drawing more than 2 million households per episode in late 1999 and became Comedy Central’s second most popular show after South Park. Kimmel and Carolla eventually exited The Man Show, making way for comedians Doug Stanhope and Joe Rogan, but the show ended in 2004 shortly after the new hosts took the stage.

In 2003, Kimmel landed at ABC for a new comedy show originally intended as a substitute for the recently canceled Politically Incorrect hosted by Bill Maher (who lost the job after he commented that the hijackers who orchestrated the 9/11 attack on the Twin Towers were not cowards). As he took his spot at ABC, immediately Kimmel was explaining to press that he wasn’t the crass, sexist jerk who occupied the leather recliner at The Man Show. “The idea that I am this guy who runs around snapping people in the ass with a towel, that’s not really me,” Kimmel said in a 2002 Observer piece. “I like to think there is a little more to me than that. I know there is.”

But even as Kimmel distanced himself from The Man Show, his success at ABC depended on viewers identifying with the personae he cultivated for five seasons. What the network really wanted was the 18 to 34 male demographic, which had largely been captured by David Letterman and Jay Leno. And the show tried to infuse stuffy ABC with a little of Comedy Central’s raunch; the show, just as The Man Show did, had a bar for the audience, but after an audience member vomited too close to a Disney executive the bar was nixed from the show in its first few weeks.

The desperation to appeal to young male viewers can be seen in its early guests: Snoop Dogg, who repeatedly flipped the middle finger and had to be censored with ABC stickers on screen, The Rock, and musicians like Coldplay and 50 Cent. A recurring segment in which comedian Andy Milonakis interviewed and pranked people on the street recalled the “Man Show Boy” bit and celebrity-filled video sketches like “I’m Fucking Ben Affleck” defined his voice in late night.

In the beginning, Kimmel joked about how Jimmy Kimmel Live! wouldn’t work out (“I will be fired from this job, it’s just a matter of how long it’s going to take,” he told Diane Sawyer in 2003), it wasn’t a failure, though certainly not a break-out success initially. By 2005 Jimmy Kimmel Live! was averaging 1.8 million viewers, whereas the Tonight Show with Jay Leno was averaging 5.8 million. Critics admired the way in which Kimmel didn’t talk down to his audience and the lack of formality in interviews. The green room for the show was covered as if it were a nightclub, as models and celebrities who weren’t even going to appear on the show tried to get in on weekend nights.

But over the years, Jimmy Kimmel Live! was largely apolitical. While jokes about politics factored into his monologues and persona, they were never the star of the show. It wasn’t until Trump was elected in 2016 that Kimmel’s programming became explicitly more political. The moment that seemed to solidify Kimmel’s image as an activist and not just a jokey commentator was a year later when the late-night host devoted a monologue to a personal story about his son Billy who was born with a heart condition. He used the extremely emotional speech as a springboard for future monologues repeatedly urging viewers to hold lawmakers accountable for healthcare reform and keeping the Affordable Care Act intact, including sparring with elected officials like Louisiana Senator Bill Cassidy.

That President Barack Obama was singling out Kimmel for being well-spoken on issues like the ACA underscored the differences between Kimmel and his late-night counterparts. Competitors like James Corden and Jimmy Fallon, whose shows are full of zany game show bits and family-friendly comedy meant to go viral, were flailing after the election of Trump. After Fallon’s 2016 interview during which he playfully rumpled Trump’s hair, critics and viewers accused him of being too bipartisan. Late-night hosts were suddenly being judged by where they fell on the political spectrum, and amid playful centrists like Seth Meyers and overtly political comedians like John Oliver, Kimmel had decided to not stay on the jokes-only side of the debate.

“How do you walk on stage and ignore it? You can’t,” Kimmel told The Hollywood Reporter in 2019. “It’s hard for me to talk about serious subjects, it takes a lot out of me. I want to be funny and it’s not fun doing anything like that.”

Kimmel is not a political radical, but in late night’s centrism, his voice has emerged as something critics and viewers celebrate. The late-night host believes his past at The Man Show, the gross sketches, the blackface, the sexism, was simply poorly executed satire long behind him; he’s now a reformed political commentator. But Jimmy Kimmel Live! exists because of The Man Show, and Kimmel can only be the down-to-earth late-night dad because he was once a beer-guzzling, sexist, a so-called “average dude,” that complained about his wife and enjoyed gazing at hot chicks. Kimmel seems to know this, as when he told Vulture that “to hear someone like me talk about equal rights for homosexual people hits harder than when people hear [Ellen DeGeneres] talk about it… to hear the guy from The Man Show.” To Kimmel, his straightness, and his history of speaking as a gleeful misogynist, actually makes him more of an authority on something like gay rights because he’s speaking from a place of straight “objectivity” instead of the real, lived experience of a gay person.

The template for America’s late-night host is that of a “regular” white guy in a nice suit, his authority as a commentator, no matter what his background, baked into the program itself. Men trusted and laughed with Kimmel on The Man Show, and they do so today during his late-night slot. Jimmy Kimmel is not successful in spite of his past work but because of it, and all the rowdy audience members who cleaned up and followed him to ABC for a different kind of man show, but a man show nonetheless.