The Stunning Transformation Of Jimmy Kimmel

Funnyman Jimmy Kimmel has been a fixture on television's late-night landscape for two decades as host of his eponymous talk show, "Jimmy Kimmel Live!" Not only has Kimmel interviewed public figures, but he has also demonstrated a fearlessness at poking fun at them — some of whom have bitten back. That somewhat lengthy list ranges from back-and-forths with NFL quarterback Aaron Rodgers to ex-president Donald Trump, and each time Kimmel has spun these feuds into comedy gold.

Becoming a late-night host may have been the fulfillment of his boyhood dream, but nobody is more surprised that it actually came true than Kimmel himself. "I still feel like the altar boy who is goofing on the priest," he mused in an interview with the Los Angeles Times. "I'm as surprised as anyone could be in this position — even to have a really good job is a surprise to me."

Having carved out his niche in late-night television, Kimmel's trek from comedy-loving teen to irreverent radio deejay to late-night legend has had plenty of unexpected twists and turns along the way.

Jimmy Kimmel was born in Brooklyn, New York, but was just 9 when he, his parents, and two siblings moved to Las Vegas. Growing up, the future comedian didn't feel there was anything out of the ordinary about living in a place nicknamed "Sin City." "I didn't know it was a weird thing to grow up in Las Vegas until I moved," he related to People. 

Looking back at his childhood, Kimmel remembered an abnormally normal upbringing, with typical experiences like little league and attending church being offset by the more offbeat aspects of the city. "But then there's all this craziness around you," he said, recalling once seeing Sammy Davis Jr. while shopping for clothes and bumping into Liberace at the supermarket. "When I was in high school, our marching band was hired to go to Wayne Newton's house and play 'Happy Birthday' to wake him up in the morning," Kimmel remembered. "So we had a 100-person marching band on Wayne Newton's front porch playing 'Happy Birthday.'"

There were some other unorthodox Vegas experiences that, to young Kimmel, felt normal at the time. "Instead of nine to five, your mom or dad might work midnight to 8 a.m.," he explained during an episode of "Jimmy Kimmel Live!" (via ABC News).

Jimmy Kimmel discovered comedy as a teenager, thanks to David Letterman and his groundbreaking "Late Night" talk show. Kimmel became a devotee of Letterman and his show, and describing his fandom as hardcore would be an understatement. Not only did his car sport a vanity license plate that read "L8NITE" (which his mom recreated for him on his birthday cake), he also took to wearing a "Late Night with David Letterman" jacket.

"I watched the show every night and little did I know that many years and many pounds later that watching the show was a great education for me," Kimmel said while paying tribute to Letterman on his show (via Business Insider) when Letterman ended his late-night run in 2015.

When Kimmel launched his own talk show in 2003, he reached out to Letterman to be his first guest — an offer Letterman refused. "I'm glad Letterman wasn't my first guest because you're already nervous enough doing your first show," Kimmel told The Hollywood Reporter in 2011. "But I would have been an absolute basket case." Letterman has, in fact, dropped by "Jimmy Kimmel Live!" a few times over the years. "David Letterman is to me what Beyoncé is to everyone else," Kimmel said before his idol's 2017 appearance on his show (via Entertainment Weekly).

David Letterman wasn't the only comic to capture the imagination of teenage Jimmy Kimmel, who also listened to the outrageous radio antics of Howard Stern (he and Stern would later wind up becoming close friends). "My Uncle Vinnie used to tape him when he was on WNBC in New York and then send me cassettes," Kimmel told The Hollywood Reporter, revealing it was Stern who inspired him to become a disc jockey at his college radio station. "I started doing a half-hour Sunday-night talk show on college radio station KUNV. That excited me more than anything I'd ever done," Kimmel recalled in an interview with Variety.

After graduating, he decided to pursue a radio career, following the familiar radio trajectory of moving from one market to another as he found work in cities ranging from Seattle to Tucson. Working his way up the radio ladder, Kimmel eventually landed at LA's KROQ in 1994, working for the "Kevin & Bean" show. The station's higher-ups hired him as a writer, envisioning a behind-the-scenes role for Kimmel, but hosts Kevin Ryder and Gene "Bean" Baxter wanted him on the air, leading him to become known as "Jimmy the Sports Guy."

"We had to fight to get him as an on-air guy. I think Jimmy looked at sports as a way to get comedy on the air. It was a great jumping off point for him," Baxter told Variety.

Jimmy Kimmel's LA radio exposure on "Kevin & Bean" opened the door to television when he accepted an offer to appear in promos for the Fox network. "It never was my plan to get into television," he told Variety, but decided to step into the industry. That gig led to further television work, and an opportunity presented itself in the form of a new quiz show for Comedy Central. "When I heard about 'Win Ben Stein's Money,' I thought okay, that sounds like a good idea," Kimmel recalled. "I was the only one who auditioned for that show. 'Ben Stein's Money' was definitely the breakthrough." 

Host Ben Stein remembered things a bit differently in a 2013 interview with Variety, claiming that he and the show's producers felt they didn't need to see anybody else after Kimmel auditioned. "We all knew Jimmy was a genius long before we were on the air," Stein said. Kimmel proved to be a standout as a sidekick, with his quick-witted wisecracks serving as the perfect counterpoint to Stein's bone-dry delivery on the game show, which debuted in 1997. 

Stein ended up taking at least partial credit for Kimmel's eventual jump to late-night television. Upon hearing that ABC was looking to launch its own late-night show, Stein called up Michael Eisner — then head honcho of ABC's parent company, Disney — and recommended Kimmel. "He called me back a long time later and said, 'Ben, you saw it first,'" Stein gushed.

Jimmy Kimmel exited "Win Ben Stein's Money" to launch a new show on Comedy Central. Teaming up with friend Adam Carolla — whom he had known since his days in LA radio — the duo created "The Man Show" in 1999. The show's title pretty much summed up the premise; a comedy that simultaneously celebrated male culture while also parodying it.

"Is this funny? My husband, whom I greatly respect, thinks so," The Globe and Mail's Leatrice Spevack wrote at the time. " I think it makes 'Saturday Night Live' look like an evening with Noel Coward." Despite — or perhaps because of — its somewhat Neanderthal nature, "The Man Show" ran for six seasons, concluding in 2004 (Kimmel and Carolla departed in 2003, with controversial comedian Joe Rogan and fellow comic Doug Stanhope tapped as replacements for the final two seasons).

Appearing on "Watch What Happens Live with Andy Cohen" in 2019, Kimmel was asked whether he felt the show would be able to survive in a more politically correct era. "I think not only would it be possible, I think it would be more popular than it ever was," Kimmel responded. "There's a certain portion of society that is outraged by the outrage and I think that they would probably find it to be exhilarating." So would Kimmel be onboard for a potential "Man Show" reboot? "No, I would never do it, no," he insisted.

When Jimmy Kimmel began shooting "The Man Show," he was married, and by the time he exited the show, he wasn't. He and his wife, Gina, wed in 1988, but split up in 2002, and their divorce was finalized in 2003. Around the same time Kimmel's first marriage fell apart, he began dating standup comic Sarah Silverman. The pair met in 2001 when she mocked him as he hosted Hugh Hefner's Comedy Central roast. "Jimmy Kimmel everybody, he's fat and has no charisma — watch your back, Danny Aiello!" Silverman recalled during an interview with "Conversations with Michael Eisner." According to Silverman, they didn't start dating until two years after that.

Kimmel jokingly praised his then-girlfriend when he told People, "Sarah is funny and smart and good to look at. Plus, she likes fat guys. What more could I ask?" In 2008, they split up after five years of dating, but got back together just a few months later. About five months after that, in March 2009, the couple broke up once again — this time for good.

The two have remained on good terms, with Kimmel lovingly roasting her when she received her star on the Hollywood Walk of Fame in 2018. "Sarah and I dated for seven years. She mentioned me in her 300-page autobiography four times," Kimmel joked (via ET). "She mentioned farting 13 times. It has always been her first love."

Replacing Bill Maher's "Politically Incorrect," Jimmy Kimmel was chosen to launch his own late-night talk show. Premiering in 2003, Kimmel promised a program like no other. Not only did he not wear a tie, but audience members could also loosen up with a drink or two at a bar in the lobby outside the studio. That, by the way, lasted all of one night, with ABC shutting down the bar after a member of the audience reportedly barfed in the view of a network executive. "Yeah, that was probably for the best ... that was unquestionably a bad idea," Kimmel mused in a 2023 interview with Variety, celebrating the show's 20th anniversary. 

Looking back on the first night of "Jimmy Kimmel Live!," the host admitted he had no idea what he was doing. "I was totally unprepared for the show itself," Kimmel recalled. It didn't help that "JKL!" struggled to book guests in the first few months, and it took Kimmel a while to find his footing as a late-night host.

"Those first few years, I still don't understand why they kept me on the air," he said. "It would have made perfect sense to remove me. But thank God they didn't have sense." Since then, of course, the show has gone on to become a huge success, racking up countless viral moments and spawning such wildly popular signature bits as "Mean Tweets."

Jimmy Kimmel made it a tradition to end each episode of his talk show by apologizing to Matt Damon for running out of time, implying that Damon is sitting in the "Jimmy Kimmel Live!" green room fuming, night after night. Of course, it's all part of a long comedy bit in which Kimmel and Damon pretend to be arch-nemeses. Over the years, Damon has appeared on "JKL!" numerous times to perpetuate the feud, including the Sarah Silverman-sung ditty "I'm f***ing Matt Damon," him crashing Ben Affleck's interview, and the coup-de-grace when Damon hijacked an entire episode.

In a 2011 interview with Parade, Damon revealed that Kimmel had been using his name to end the show for more than a year before he actually guested. When the actor met Kimmel for the first time backstage, he asked for an explanation. Kimmel told him that he had just completed a dull show lacking in star power, and he joked that Damon — the first celebrity who popped into his mind — had to be bumped to the next episode, making Kimmel's producer break out into laughter. The host repeated the bit the next night, with the inside joke eventually becoming an ingrained part of the show.

That was evident in Damon's appearance in a "JKL!" primetime special, in which Kimmel offered a long, flourishing introduction — and then told the star that they had run out of time. "I'm sorry, Matt," Kimmel said with mock sincerity. "Can you come back tomorrow night?"

While Jimmy Kimmel's feud with Matt Damon is fake, there was nothing bogus about his anger toward late-night competitor Jay Leno. It stemmed from NBC's botched handling of Conan O'Brien replacing Leno as host of "The Tonight Show," a deal that forced O'Brien to wait years until finally ascending to the late-night throne. When the time came in 2009, Leno stuck around for his own talk show, "The Jay Leno Show," at 10 p.m., with O'Brien's "Tonight Show" bumped to much later in the night.

This debacle ended up being a ratings disaster that resulted in O'Brien being ousted after just seven months while Leno resumed hosting "Tonight." When Kimmel appeared on Leno's show, Leno asked him to recall his best prank. "I think the best prank I ever pulled was, I told a guy ... five years from now, I'm gonna give you my show, and then when the five years came I gave it to him and then I took it back almost instantly," Kimmel quipped.

There was more to the story than Kimmel avenging O'Brien. Appearing on Bill Maher's "Club Random" podcast, Kimmel divulged that Leno had been in serious meetings to launch an 11:30 p.m. show on ABC, which would become the lead-in for Kimmel's show. The two had numerous discussions, with Kimmel assuming they'd become friends — until Leno announced he was remaining at NBC, without bothering to let Kimmel know. "I suppose I should have called Jimmy and explained to him again," Leno told Deadline. "But I didn't."

Molly McNearney has been on the staff of "Jimmy Kimmel Live!" since the beginning, initially hired as a writer's assistant before eventually being promoted to head writer. It wasn't exactly love at first sight for McNearney and her boss. "When I first met him, he insulted me!" she said in a 2014 interview with Glamour, recalling when he learned she'd competed in triathlons, "Jimmy looked up at me and said, 'That is really stupid! What a waste of time.' That was the first and only thing he probably said to me the entire first year of working there."

A few years later, they began dating, when Kimmel discovered the way to McNearney's heart was through her stomach. "He cooked for me, and that was it," she told Glamour. "It sealed the deal."

They got married in a star-studded 2013 ceremony that included such A-listers as Howard Stern, Ben Affleck and then-wife Jennifer Garner, Jennifer Aniston and then-fiancé Justin Theroux, Ellen DeGeneres and wife Portia de Rossi, and many more. The couple welcomed their daughter, Jane, in 2014, and then their son, Billy (who required heart surgery when he was just three days old), in 2017. Kimmel is also the father of daughter Kate and son Kevin from his first marriage.

During his two decades as a late-night host, Jimmy Kimmel also managed to establish himself as one of television's most sought-after award show hosts, graduating from the American Music Awards to the Emmys, then being tapped to host Hollywood's biggest night, the Academy Awards. Clearly, he did something right; Following his debut in 2017, he was invited back in 2018.

When producers asked him to host, Kimmel was well aware that he wasn't the first choice; "Which I was okay with — I understand it," he told the Los Angeles Times. After hosting a second time, Kimmel felt he did what he set out to accomplish. "I did not think I would ever do it again," he explained. "I know how much work goes into them, so I thought, 'Yeah, I don't necessarily want to do this ever again.'"

But, much like Michael Corleone in "The Godfather Part III," just when he thought he was out, Kimmel got pulled back in to host the 2023 Oscars and did it again in  2024. He decided to return because there had been some popular movies nominated, which he figured could help him connect with viewers. "I made a joke about 'Moonlight' that made it clear to me that the vast majority of the room had not seen the movie, even though it won best picture," he recalled, referencing his first stint as host.

In 2022, Jimmy Kimmel extended his contract with ABC, signing on for three more years of "Jimmy Kimmel Live!" With the end of that contract looming, could that mark the end of his career in late-night? "I think this is my final contract," Kimmel told the Los Angeles Times in 2024, but admitted that he expressed similar sentiments in the past, only to return. This time, though, the timing felt right. "I still have a little more than two years left on my contract, and that seems pretty good," he added. "That seems like enough."

There's no escaping the simple fact that producing a one-hour TV show five days a week is a serious grind. However, whenever Kimmel has been away from it, he has found himself missing the action. "It's hard to yearn for it when you're doing it," the host added. "But then, I take the summer off or I go on strike, and you start going, 'Yeah, I miss the fun stuff.'"