Has there ever been a more improbable late-night star than Jimmy Kimmel?  For our money, there was never one less qualified when he got the gig. Think about it:  Letterman and Leno each had several stints filling in as host of The Tonight Show, virtually auditioning for the gig while generating the necessary reps.  Jimmy Fallon had years of live late-night TV under his belt from his SNL days.  Stephen Colbert headlined his own Comedy Central show before shifting to CBS.  James Corden?  Sure, no talk show experience but he did have a Best Actor Tony Award and a comedy BAFTA to his credit. Maybe the closest inexperience analog was SNL writer Conan O’Brien, but at least he had Harvard and Lorne Michaels behind him. 

Kimmel, on the other hand, got the prime late-night spot on ABC based on these highly suspect qualifications:

 * Several jobs on the radio as part of a disc jockey team, most of which found him getting canned for pulling stupid office pranks

 * Ben Stein’s sidekick on Win Ben Stein’s Money.  We know Kimmel wasn’t the main guy since it wasn’t called Win Jimmy Kimmel’s Money.  

 * Co-host on Comedy Central’s The Man Show, goofing around with the much louder and more obnoxious Adam Carolla.  Kimmel’s gone on to have the better career, but Carolla was the alpha of that particular comedy team.  Notice who gets introduced first on the show--it ain't Kimmel.

And … that’s it.  Until Jimmy Kimmel Live!, Kimmel had never even flown solo, always sharing the spotlight with another comic voice that seemed more distinctive than his own. 

ABC’s decision is even more baffling because the network chose Kimmel over his Comedy Central co-worker Jon Stewart, the man behind the highly popular and well-regarded Daily Show. Stewart made sense -- appealing to the same young demographic that you’d hope for with Kimmel, but with much more experience as the guy out front of a comedy television show. You could forgive 2003 viewers for asking:

What the hell?

It’s not as if ABC was proven right, at least not in the beginning.  After the show premiered, The Hollywood Reporter fired up the blowtorch, deriding “the aimlessness of the entire production, the disorganization of the host, and the overall lack of anything remotely resembling humor.”

And Hollywood Reporter was just getting warmed up!  “It’s been reported that Kimmel has a budget for writers, but nothing in the premiere indicated any had been hired. Three taped pieces of comments at the Super Bowl by Arnold Schwarzenegger looked as though they had been picked up from the Entertainment Tonight cutting-room floor.”

Kimmel’s self-assessment wasn’t much kinder. “If you watch the early episodes of my talk show,” he told Vulture, “you’ll see that I was very uncomfortable onstage.” 

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Maybe Kimmel's discomfort was because he dressed like a pimento-stuffed olive?

The show stumbled out of the gate with dumb decisions. Kimmel dressed like a shlub. And he decided to have an open bar so the host, guests, and audience could get ripped during taping. Sure, it sounds like fun until someone nearly yaks all over ABC executives -- which is exactly what happened on the show’s first night. As Semisonic might have sung, Closing time, you don’t have to go home but you can’t puke here.  

And yet.  

Despite Kimmel’s lack of a resume, despite his early missteps, despite a history of lowbrow comedy that involved bikini-clad babes bouncing on trampolines, ABC did get it right.  Kimmel somehow became a dean of late night, gaining polish and panache, pulling off genius comedy bits, and becoming an outspoken advocate for health care and gun reform.  What did ABC see that no one else was seeing?

Maybe it’s what The Ringer’s Bill Simmons noticed when Kimmel lured him from ESPN to write for the new show. It wasn’t just Kimmel’s sense of humor (which was a lot like Simmons’ own).

“He has an innate knack for making people comfortable, regardless of the situation, which is the best possible quality for a talk show host,” Simmons wrote in his Page 2 column. “He has the good sense to surround himself with quality people. His energy is amazing -- there isn't a second of the day when he isn't trying to make somebody laugh, only there isn't the same desperation like there is with someone like Conan O'Brien.”

(Taking a quick Simmons break to say: Wow! What did Conan do to catch those stray bullets?  Anyway, back to Bill …) 

“And it's humanly impossible to dislike Jimmy -- he's the proverbial Guy's Guy, only he's funny enough and creative enough to get paid for it. I love the fact that some were surprised when ABC hired him, thinking that he couldn't do anything beyond a formulaic vehicle like The Man Show or those football segments on Fox. Fine. Think that. You will be pleasantly surprised in a few months.”

And … that’s sorta kinda what happened.  It took more than a few months, but Kimmel’s show slowly gained viewers and grudging critical acceptance. And maybe the network knew a few things before they hired The Man Show guy.

“Hey, I know this sounds crazy,” Kimmel told Playboy back in 2003, “but ABC did some research, and a greater percentage of college-educated people watch The Man Show than Nightline. Smart people can be perverts, too.” 

That research showed ABC that there was an opening for an Everyman.  “He’s a much more raw, blue-collar guy than has ever sat in that seat and done that show,” says former ABC exec Michael Davies.  In that sense, maybe Kimmel’s lack of show-biz experience played in his favor. 

But even blue-collar guys have to clean up after a while.  He eventually put on a tie, noting “if you want to do a talk show on network television, you’re probably going to wind up having a desk and a band, wearing a suit and having a sidekick.”  He got so mainstream that he was chosen to host the craziest Oscars ever, gracefully handling the chaos when Warren Beatty and Faye Dunaway somehow announced the wrong winner. 

He grew a beard, lost weight, and suddenly became handsome. The doofus behind The Man Show somehow became a respected elder statesman. And now that Kimmel has scaled the mountain -- he’s been the highest-rated late-night talk show among the 18-49 crowd for several weeks this year -- he’s thinking about hanging up the spurs.

Kimmel Live! debuted in 2003, so we’re nearly 20 years in--and Jimmy’s contract is up next year.  "I wish I knew (what) I was gonna do," he says.  "I have moments where I go, ‘I cannot do this anymore.' And I have moments where I go, ‘what am I gonna do with my life if I'm not doing this anymore?' It's a very complicated thing.  Eventually, I am going to have to stop doing this. I'm not going to do this forever."

There’s a part of us that hopes Kimmel moves on to whatever comes next, only to see what ABC has in mind for a replacement.  We’re pulling for another outside-the-box oddball who makes absolutely no sense.  They’ll probably be great.

For more ComedyNerd, be sure to check out:

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