The Untold Truth Of Jimmy Kimmel

It's safe to say that Jimmy Kimmel has earned his place among late-night greats Jay Leno, Conan O'Brien, and David Letterman, but the former Win Ben Stein's Money host was an unlikely choice when ABC decided to break into the late-night talk show scene in 2003. In fact, Jimmy Kimmel Live! barely made it past its first disastrous year. The situation got so bleak, Kimmel himself wanted the show to be cancelled. 

Clearly, things worked out. Along the way, Kimmel fell in out and out of love, started a few feuds, and became a surprisingly powerful provocateur in the world of politics. Not bad for a kid from Vegas who was may be a little too obsessed with a particular late-night host. Keep reading to learn more.

Kimmel has often joked that he never planned to be a late-night talk show host, but the truth is, he's been obsessed with Letterman since the fourth grade. 

In a Time tribute to Letterman's retirement in 2015, Kimmel talked about his idol. "Every school night, I watched with the kind of simmering fervor described in newspaper profiles of teens who run away from home to fight for ISIS. First period started at 7:35 AM, but Dave was more important than sleep," Kimmel wrote. "On the day I turned 16, I blew out candles on a Late Night birthday cake. I had 'L8NITE' vanity plates on my first car. Dave smoked cigars, so I smoked cigars."

Kimmel modeled his own career after Letterman's, but he never expected it to work out so well that he'd one day find himself competing against his hero.

Growing up, Kimmel's family encouraged him to pursue a career in art, but his teachers encouraged his natural knack for comedy (despite the inevitable classroom disruptions). According to The New York Times, Kimmel knew he had to work in radio. Why? Because he read in Playboy that Letterman started in radio. While bouncing around Seattle, Tampa, and Palm Springs with a then-unknown Carson Daly as his sidekick, Kimmel eventually landed at KROQ in Los Angeles, where he met a boxing instructor that changed his life.

"Jimmy and Adam (Carolla) were peas in a pod," DJ Gene Baxter (better known as Bean) told Variety. "It was such happenstance that they met at the right place, at the right time. We came up with this crazy idea of a boxing battle between Jimmy and another guy on the show, and Adam was the trainer." Bean said there was "instant chemistry" between Kimmel and Carolla. "They have the comic sensibilities and cracked each other up. The Man Show was an outgrowth of that."

But launching The Man Show wasn't as smooth a ride as Kimmel and Carolla's instant friendship.

In 1997, Kimmel caught a break as the co-host of the Comedy Central game show Win Ben Stein's Money. According to Stein, Kimmel was the show's first audition and "we knew we didn't have to see anyone else after that."

Despite the show's popularity, Kimmel was still auditioning for other television shows, and it wasn't going well. In an interview with The New York Times, Kimmel recalled one producer telling him that he "wouldn't appeal to women," and that's when he got the idea for The Man Show. He worked out the concept with Carolla, and the two pitched it to ABC. The network initially loved the idea of an "anti-Oprah show" with a "heavy emphasis on midgets, explosions and beer."

However, Kimmel and Carolla reportedly delivered "the most poorly received pilot ever," according to an ABC exec, and the network passed. While The Man Show wasn't right for the Big 3, it surprisingly launched a bidding war among cable networks. Comedy Central won, and Kimmel suddenly looked like the channel's golden boy, but he wasn't done trying to find his place on the small screen.

Even while appearing on two Comedy Central shows, Kimmel continued to hunt for other opportunities. He landed a spot doing 15-minute segments on Fox NFL Sunday thanks to his early work as Jimmy the Sports Guy for KROQ. The comedic spots gave the pregame show a ratings bump and gave Kimmel some name recognition when ABC began search for a late-night host. 

However, according to The New York Times, Kimmel's Fox Sports castmates seriously "derided him," and when he landed a meeting with senior Fox executives, he was offended to learn that the brass wanted him to "start a late-night talk show at a Fox station in Minnesota and maybe expand to other local stations from there." 

That wasn't the only relationship going south for Kimmel.

As Kimmel's star continued to rise, his 14-year marriage to Gina Maddy was falling apart. The couple separated in 2002 and agreed to share custody of the children, but ten years later, HuffPost reported that the exes were still "not on good terms."

That might have a lot to do with rumors about when Kimmel's relationship with comedian Sarah Silverman started. According to Fox News, there was some noticeable overlap between the downfall of his marriage and his new relationship with Silverman. Fox called the romance "one of the worst kept 'open secrets' in Hollywood." It was clearly a stressful time for the future late-night host, but he still had a bumpy road ahead.

Despite idolizing Letterman and doggedly building a career in television, Kimmel never believed he'd actually become a late-night talk show host on network television. Even as Jimmy Kimmel Live! neared its premiere, he seemed clearly confused about how all of this was happening and repeatedly joked in promotional interviews that even he wouldn't watch his own show over Letterman's.

In fact, Kimmel reportedly had to be tricked into a meeting with ABC in the first place. The network supposedly began pursuing him after passing on Jon Stewart. (Yes, that Jon Stewart.) During the meeting, which Kimmel's agent made him attend even though Kimmel had no interest in hosting a variety show, ABC President Lloyd Braun talked to Kimmel about late-night television but supposedly didn't mention that ABC wanted a show of its own. When Kimmel returned home, he got a call from his agent saying the network wanted him to be its late-night host.

"I thought, there must be a mistake," Kimmel said. "It happened so quickly. And there was no—it seemed like there was no thought put into it," he added with a laugh.

Kimmel was on his way to following in Letterman's footsteps, but while Jimmy Kimmel Live! obviously became a success, it was an embarrassing trainwreck at first.

When Jimmy Kimmel Live! premiered, it was generally considered to be dead on arrival, according to critics. In Kimmel's defense, he wanted to differentiate himself from Leno and Letterman by going for a less-polished, more everyday guy approach to late-night, which is what endeared to him ABC in the first place. Unfortunately, Kimmel veered a little too close to his Man Show antics, and the late show became a jumbled mess of drunken guests, rowdy audience members, and boring interviews...if and when the show actually booked a celebrity. The situation got so bad, Kimmel reportedly started hoping ABC would cancel the show, which almost happened.

"There was always talk of that." he told The Hollywood Reporter. "And I could almost mark each one of those times because there were probably six or seven times where the show was going to get canceled and I would've welcomed it at that time because I really just was out, I was spent."

Eventually, Kimmel course-corrected, realizing he needed to cater to a wider audience than just 18 to 34-year-old men. "If you want to get women to watch the show, you don't throw darts in Steve-O's a**. We kind of just smoothed some of the edges," he told HuffPost.

With time to grow, Jimmy Kimmel Live! became a dependable hit for ABC, and the ratings kept rising. Kimmel had made his mark, and it wasn't long before he started using that clout.

In 2007, Kimmel filled in for talk show host Larry King and made headlines after calling out Gawker editor Emily Gould over the site's popular "Gawker Stalker Map," which promised to "visually pinpoint the location of every stalkworthy celebrity as soon as they're spotted" by using reader submissions. Kimmel had been spotted by the site and accused of being publicly intoxicated when he was really coming home from a child's birthday party, so he had an ax to grind with Gawker. In the process, he also landed some crucial blows on Gould, who attempted to defend the questionable feature.

"So people are out, and they have their cellphones and they can send a little message to you and say, 'I just saw Gwyneth Paltrow at the movies,' and that way when Gwyneth Paltrow comes out of the movies, there could be at least a dozen psychopaths waiting for her," Kimmel said (via Mediaite).

The incident became such an infamous critique of "citizen journalism" that Aaron Sorkin recreated the exchange on The Newsroom. The situation also highlighted a more mature Kimmel who had some even bigger changes coming down the road.

In 2009, Kimmel and Silverman ended their relationship, but they've remained on good terms and she often appears on his show. A few months after things ended with Silverman, Kimmel began dating his co-head writer, Molly McNearney. You might think that dynamic could be weird, but the three reportedly get along great. No wonder Kimmel put a ring on it and married McNearney in 2013.

A year later, the couple welcomed a daughter, Jane, who began bringing out the edgy comedian's softer side, but Kimmel's life would change dramatically when his son arrived in 2017 with a harrowing condition.

When Kimmel's son, Billy, was born in late April 2017, doctors discovered he had a congenital heart disease that required immediate surgery. The ordeal had a significant impact on Kimmel, who returned to his show early for the sole purpose of delivering an emotional monologue on affordable healthcare.

"Before 2014, if you were born with congenital heart disease like my son was, there's a good chance you'd never be able to get health insurance because you had a pre-existing condition," Kimmel said through tears (via Entertainment Weekly). "If your parents didn't have medical insurance, you might not even live long enough to get denied because of your pre-existing condition. If your baby is going to die and it doesn't have to, it shouldn't matter how much money you make."

On the same show, Sen. Bill Cassidy coined the phrase the "Jimmy Kimmel Test" and promised that "no family should be denied medical care, emergency or otherwise, because they can't afford it." But months later, Cassidy proposed a bill that failed the Jimmy Kimmel Test on every level, and the late-night host wasn't having it.

"This guy, Bill Cassidy, just lied right to my face," Kimmel said in another powerful monologue. The bill died before it came up for a vote, which made little Billy pretty happy! It seems there's nothing this kid can't do, including helping his old man bury the hatchet with a long-time rival.

For years, Kimmel had been relentless about his dislike for Leno. In the lead-up to the premiere of his own late-night show, Kimmel told The New York Times that he knew Letterman's audience was too smart to watch Jimmy Kimmel Live!, but he was pretty sure he could siphon off some of the "stupid" people who watch Leno. Ouch.

The situation reached a boiling point in 2010 when O'Brien took over The Tonight Show only to have Leno take his old job back. It was an uncomfortable situation, and Kimmel jumped right into the fray. According to Entertainment Weekly, Kimmel filmed an entire episode of Live doing a scathing impression of Leno, and that was just the beginning. Kimmel even went on Leno's 10 p.m. show and mocked him via satellite.

When Leno asked about his famous pranks, Kimmel responded, "I think the best prank I ever pulled was, I told a guy that 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. It was hilarious." Talk about harsh. It's no wonder the two didn't speak for years.

All that changed when Leno saw Kimmel's emotional monologue about his son and reached out. In an interview with The Hollywood Reporter, Kimmel was clearly touched and had nothing but nice words to say about his former rival.

He also had bigger fish to fry.

Just a few short weeks after Kimmel's viral takedown of the Graham-Cassidy bill, the late-night host once again found himself wading into political waters after the deadly mass shooting in his hometown of Las Vegas on Oct. 1, 2017. In another emotional monologue, Kimmel said he refused to believe that nothing can be done to prevent future tragedies.

"There are a lot of things we can do about it. But we don't," Kimmel said (via Deadline). "Which is interesting, because when someone with a beard attacks us, we tap phones, we invoke travel bans, we build walls. We take every possible precaution to make sure it doesn't happen again. But when an American buys a gun and kills other Americans, then there's nothing we can do about that. Because the Second Amendment. Our forefathers wanted us to have AK-47s is the argument."

Kimmel also didn't hold back on criticizing politicians, saying "the NRA has their balls in a money clip," and he lambasted White House Press Secretary Sarah Huckabee Sanders for saying that the immediate aftermath of the shooting was not the time for debate. Kimmel's fiery barbs quickly made headlines, and they proved that the late-night host had become a force to be reckoned with in politics.