Late Night’s Late Bloomer

Famous athletes have their bizarre pregame rituals, and so, it seems, do comedians. It’s minutes before Jimmy Kimmel Live!’s 7 p.m. taping June 9, and half a dozen members of the host’s staff are huddled around him in his sprawling Hollywood office. An associate producer has crafted a tongue-in-cheek line that the group has planned to chant before Kimmel takes off, a tradition that dates to Kimmel’s first show, eight-and-a-half years ago.

As Kimmel nods along, the group singsongs in unison, “Every night we send Jimmy on his way … and then we rummage through his shit.” Several of them glance up for the host’s approval. He cracks a smile. They continue the chant: “Best show ever! Best show ever! Best show ever!” Kimmel, now heavily made up and camera-ready, extends his fist and bumps it against those of everyone gathered before darting out the door. “It’s the most nonmotivational motivational chant,” the host will later say with a laugh, acknowledging that he often enters the theater still scratching his head.

On this night before taking the stage, Kimmel, 43, slips into edit bay No. 3 to take one final look at a new Schwarzenegger taped spoof, starring Kevin Nealon as Arnold and Kathy Griffin as his mistress, prepared only hours earlier. He suggests an editor reorder the two-and-a-half minute video’s ending so that viewers get their first glimpse of the former governor’s love child — a diapered dwarf nestled in Griffin’s arms — after he grunts, “Hasta la vista, baby.” From there, Kimmel pushes into a cramped elevator headed for stage level. He stops briefly to greet his guest and friend J.J. Abrams — there to plug his new film Super 8 — in the greenroom. Two producers trail him as he enters the cozy 200-person El Capitan Theatre to thunderous applause.

After riffing on the week’s NBA Finals, he settles in on his target of choice: disgraced Rep. Anthony Weiner: “Is it too late for him to tell people it’s pronounced Why-ner?,” Kimmel deadpans. Sixty minutes later, after a viewing of the Schwarzenegger skit, some hearty banter between guests Griffin and Abrams and an ear-piercing performance by musical guest Friendly Fires, it’s over.

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If David Letterman is late-night’s elder statesman, Kimmel is his goofier, prank-prone little brother. He isn’t going to delve into pointed political commentary like Comedy Central’s Jon Stewart, but he’ll stand up to late-night’s bully, Jay Leno — on Leno’s show — when he feels it’s deserved (more on that later). And he’s been that way since 2003, when ABC — desperate to get into the lucrative late-night comedy business and to replace Bill Maher’s Disney-unfriendly Politically Incorrect — hired him after failing to lure Letterman. Lloyd Braun, who was entertainment chairman at the time, wanted a fresh face that could draw young men, an elusive and desirable late-night demographic. Kimmel, a likable “regular guy” fresh off of Comedy Central’s testosterone-fueled Man Show, fit the bill.

Now, despite an estimated $8 million salary and a far larger profile nearly a decade later, Kimmel appears to remain that same guy who once trotted out without a script and served alcohol to his studio audience: the funniest frat boy in the house. His everyman shtick differentiates him from Letterman (arguably crankier), Leno (phonier), Conan O’Brien (smugger) and Jimmy Fallon (sillier). But mixed in with Kimmel’s irreverent, even smart-ass sensibility is a sweetness and decency that plays to a broad network audience, both male and female. And it’s growing. Kimmel recently wrapped his most-watched season in four years and his best May sweep yet. According to Nielsen, 1.7 million viewers regularly tuned in this past season — a far cry from late-night leader The Tonight Show With Jay Leno, which lures 3.7 million viewers a half-hour earlier, but up 4 percent from Kimmel’s show last year. In the all-important 18-49 demo, Jimmy Kimmel Live! ticked up 3 percent.

In a world of high-strung crash-and-burn hares, Kimmel has played the part of the tortoise, quietly staying out of late-night’s musical chairs to cultivate a hit show. “You’re looking at a broadcast world where people are struggling to stay flat,” says ABC Entertainment Group president Paul Lee, “and here’s a guy who is actually gaining audience.” Advertisers who are treated to his famous industry roast at ABC’s annual upfront presentation in New York have taken notice. The show generated $85 million in commercial ad revenue last year, not including fees for Kimmel’s throwback live ads and many web tie-ins, reports Kantar Media. (An insider suggests the figure is closer to $100 million.)

Of course, Kimmel has been helped by an extra few minutes and audience heat from red-hot Nightline that allowed him to start right at midnight, instead of 12:05 a.m. — a vote of confidence by ABC brass — and a steady string of clever celebrity-packed videos that have zoomed around the web. (This year alone, the videos have been viewed 103 million times on YouTube.) But perhaps the biggest game-changer came in early 2010, when Kimmel proved that he had the gravitas, guts and chops to go head to head with Leno. As is now late-night legend, Leno had reneged on an earlier decision to move on from his post at Tonight Show, leaving his short-lived replacement O’Brien jobless and Kimmel — who had once seen Leno lobby for his spot at ABC — fuming.

Kimmel did an entire show dressed as Leno, complete with a wig and fake chin. The parody elicited a call from the then-10 p.m. host, who invited Kimmel on his show the following night, perhaps attempting a keep-your-enemies closer approach. “I had just made fun of the guy,” recalls Kimmel, a smirk now peaking through. “I had exaggerated everything that’s annoying about him and physically looked like a clown. It’s bad enough to run into somebody if you’ve just made fun of them, but to be on television with them?”

Kimmel says he agreed to appear on Leno’s program because he assumed — wrongly — that they were going to discuss what had just happened. “I didn’t know that it would be one of those, ‘Oh, we’ll mention it quickly at the top and then move past it types of things.’ That’s what I objected to. I didn’t want to be marginalized like that,” he says of the uncomfortable segment in which Kimmel consistently turned the tables on Leno.

Not long into the interview, Leno innocuously asked him what was the best prank he had ever pulled, to which Kimmel said, “I think the best prank I ever pulled was, I told a guy once, ‘Five years from now I’m going to give you my show,’ and when five years came, I gave it to him, and I took it back, almost instantly.” Kimmel’s response to Leno’s follow-up about whether he had ever ordered anything off the TV had even more bite: “Like NBC ordered your show off the TV?” And then came the question, “Is there anything you haven’t hosted that you want to host?” Kimmel took a second and then fired: “Oh, this is a trick, right?” he asked. “Where you get me to host The Tonight Show and then take it back from me?” Leno returned from the segment stunned, telling Oprah Winfrey weeks later that he had been “sucker-punched” by the ABC host. The two men haven’t spoken since.

The experience reminded Kimmel of his radio days, when everything, he says, was a battle. “I would be lying if I said it wasn’t a lot of fun,” he admits, the smirk back on his face. “I was very nervous, but it was thrilling, it really was.”

For Kimmel, a devotee of Leno’s No. 1 rival, Letterman, the performance got the industry as well as the public’s attention in a way he never before had. But to hear his longtime agent James Dixon tell it, Kimmel, a lifelong student of late-night, was destined for this kind of success.

Some children obsess over cars, others over dolls. As a kid growing up in Las Vegas, and before that in Brooklyn, Kimmel did so over Letterman, the man for which he now competes for viewers for a half-hour Monday to Friday. (At the time, Letterman was hosting Late Night on NBC.) Kimmel would wear a Late Night With David Letterman jacket and celebrate his birthday with a Late Night cake. By the time he reached driving age, Kimmel’s first car, an Isuzu I-Mark, had a L8Nite vanity plate and his friends would come to his house for Late Night viewing parties. “I mean, I’d draw Dave’s face on every book cover. I was like a teenage girl in love with him,” Kimmel laughs, likely only half-kidding.

Letterman declined Kimmel’s invitation to be his first guest — a letter that is now framed in Kimmel’s office. Asked for his thoughts on Kimmel, Letterman, who has yet to appear on the ABC show, responded to The Hollywood Reporter with a few humorous words in an e-mail: “Jimmy Kimmel, a lovely man, really. Always kind to me, which means more than you could know to a man of my age. Did I mention likable? Well, Jimmy wrote the book (on likability). Did I mention funny? Well Jimmy wrote the book (on likability). I can’t tell you what a shock his passing has been to me and my family. We won’t see the likes of him again anytime soon.”

Perhaps knowing the importance of his son’s late-night fixation, Kimmel’s father — along with his mother — is now a fixture at the show. (The host’s staff is filled with other family members, including his brother, cousin and uncle.) “I’d be proud of him if he was a plumber,” says the senior Kimmel, a retired IBM executive. “But Jimmy did exactly what he said he wanted to do at 14: be David Letterman.” (Since 2000, Kimmel has been a guest on Letterman’s show six times, and each time he is terrified. “Dave’s approval is so important to me,” he explains. “When you’re a teenager, you don’t know people in Hollywood, so the way I judged them is, if Dave seemed to like them, I liked them. I felt like as an adult, I have to abide by that because if Dave didn’t like me, I must be an asshole.”)

Knowing that Letterman, along with his other idol, Howard Stern, had used radio as a launchpad, Kimmel jumped at the first radio offer that came his way. A program director for the local college station in Las Vegas set the still-in-high school Kimmel up with a Sunday-night slot during the mid-1980s and left it to him to find the guests. Kimmel still remembers leafing through the Yellow Pages looking for “funny things in Vegas” for his first show. “I came up with this man who in his Yellow Pages ad said he was a hairstylist to the stars, so I brought him in and interviewed him about some of the hairstyles,” says Kimmel, his smile growing wider. “When I got home, my parents, my sister and all of my friends had listened to it, and they were so excited. I was just so turned on by that.”

He would spend the next 12 or so years bouncing around from one station to the next, pissing off program directors at every stop. Larry Sharp, Kimmel’s boss at his first paying gig at Seattle’s KZOK, remembers him being “unwilling to listen to an old guy telling a 20-year-old what to do.” Able to chuckle about it now, Sharp recalls Kimmel putting his feet up on his boss’ desk — an infuriating and frequent move, says Sharp — with two words directed at him scribbled on the bottom of his shoes: “F– You.”

Although Kimmel maintained some of that brassy confidence — he still regularly prank calls his parents (they fall for it every time, he says) and sends out infamous Christmas cards on behalf of his agent as an annual gag — he has matured. “Believe me, I can now understand why that didn’t fly,” he says, shaking his head.  “But at the time, I didn’t know any better, and when you’re in radio, you’re getting paid $20,000 a year to get fired every 10 months or so.” Along the way, he’d drop out of college, get married (and later divorced) and have two kids (now in their late teens).

By 1994, he had landed at Los Angeles’ KROQ, where he became the sports guy on The Kevin & Bean Show. It was one of only two radio gigs that Kimmel wasn’t fired from, and it caught the attention of  TV producer listeners. Among them was Michael Davies, then an ABC studio exec drawn to Kimmel, who was being pitched as a game show host. “Despite a fairly weak format and awkward attire — he was wearing the worst suit ever worn in the history of men wearing bad suits — Jimmy was just brilliantly funny, spontaneous and really able to hold an audience,” says Davies. But Kimmel kept turning down projects Davies offered. “I was weirdly picky for someone who was making $50,000 a year,” says Kimmel, now sartorially improved and 20 pounds lighter. (“I’ve been trying not to eat like I’m competing in a Nathan’s hot dog-eating contest.”)

But then came Win Ben Stein’s Money, a quirky Comedy Central hit that earned Kimmel a Daytime Emmy. Next was The Man Show — a raucous and hugely popular comedy series featuring such segments as “girls on trampolines” and a “Juggy Dance Squad” of buxom models co-hosted by Kimmel and fellow radio personality Adam Carolla — that Davies originally developed at ABC. The network balked. Six or so cable channels swooped in with offers, and Kimmel and his partners settled on Comedy Central.

Crank Yankers (also Comedy Central) and The Andy Milonakis Show (MTV and MTV2), both of which Kimmel co-created and produced under his Jackhole Industries banner, followed. Although he is tight-lipped about details, Kimmel is working on another comedy series with Milonakis.

By 2002, with Braun looking to move ABC into late-night, Davies suggested Kimmel as host. (Stewart and Greg Kinnear were among other names bandied about.) Within hours, Braun was in stitches as he watched Kimmel tapes. Says Braun, “He was different from everybody else who was on late-night television at the time because he was going to speak to a younger, male demographic — a very attractive and lucrative demo — and his whole sensibility was just different.”

His only fear was that Kimmel wouldn’t connect with ABC’s distinctly female-skewing audience. “The big edict was, do what you do, but do not do The Man Show,” recalls agent Dixon. Interestingly, Kimmel’s show now is the most female-skewing of the late-night offerings, with women comprising 64 percent of his viewership. (For Kimmel, that has meant fewer dwarf jokes, though casting one as Schwarzenegger’s love child was too good to resist, he says.)

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 “Booking the show was hell,” recalls Braun of the early days, leaving the host to rely on his relationships. Says Kimmel: “There were many days when I’d get a call like, ‘We have no guests tonight.’ Thank God for people like Adam Carolla, [then-girlfriend] Sarah Silverman, Ben Stein, David Alan Grier and Kathy Griffin. I knew we could always get one of them to come on the show.”

Although there’s still a pecking order among the late-night guest bookers — Leno and Letterman’s shows remain at the top — Kimmel comfortably inhabits a space as an insider in an insider’s world, where he continues to add industry types as friends. His greenroom — with a fully stocked bar, pool table and many celebrity occupants — is considered one of the best hangouts in Hollywood; ditto for the many parties at his West Hollywood home, where Kimmel frequently doubles as host and chef. (Cookbooks and a kitchen fill his office, another common gathering place.)

Interestingly, the A-listers he knows least well — and, in some cases, not at all — are his late-night rivals. He’s met O’Brien and Craig Ferguson only once and has never met Fallon. Kimmel says he doesn’t watch any of their shows for fear of being influenced but claims, “The shows are more competitive than the hosts are.” (He knows and shares an agent with Stephen Colbert and Jon Stewart and will watch their Comedy Central series when he has time.)

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Unlike many of his late-night peers, Kimmel didn’t come up doing stand-up, a detail that has likely given him his sharpest point of differentiation. Rather than stand before a studio audience rattling off jokes for eight minutes the way a Letterman or Leno will do, Kimmel has long laced his monologue with several preproduced comedy bits  — be they doctored clips or celebrity-heavy productions — that he and his producers realized early on could live and thrive on any platform.

On this night, he turns to the projector to poke fun at Weiner. After displaying a suggestive carrot — “We can’t show you the photo because of strict anti-penis laws” — he rolls a clip, a politically themed PSA for “No Testicles, No Problem.” After flashing pictures of other disgraced politicians and a closing line, “Hillary Clinton approved this message,” the clip wins even more than laughs it did at the day’s 1 p.m. run-through. (At that time, the jokes, which Kimmel has been whittling down since his writers turned them in at 11, are cut still more, depending on how they play.)

“He really has his finger on the pulse of the culture,” says ABC’s Lee. “He doesn’t sit there as some late-night icon; he’s actually creating these viral videos and other stuff that live beyond the show.” Kimmel recognized quickly that the web was a way to reach the younger viewers who don’t watch late-night TV, and by 2008, he and his team were badgering ABC to give them their own YouTube channel, citing the millions of views the show’s pirated fare was garnering there. Eventually ABC executives agreed to let them control and update an official Jimmy Kimmel Live channel. The ads that Kimmel’s staff, along with YouTube, is out selling will add between $1 million and $2 million in revenue to ABC-owned Jimmy Kimmel Live! this year.

Still, the host has mixed feelings about the digital prowess that might be the barometer for late-night’s future success. On the one hand, Kimmel is thrilled with the audience he’s been able to garner. “If you look at the number of views we get compared to any other show — not just late-night shows, any other show — we’re way ahead,” he says. “We have as many people watching on the Internet as we have watching on television.” On the other, he has as many people watching on the Internet as he does on television. “I think ultimately it hurts our ratings because people know that they can look at it online,” he admits.

Not that Kimmel has any plans to slow down. The site adds nearly 50 new videos a week, a mix of show clips and pretaped videos, which can cost between $5,000 and $100,000 to produce (the majority fall within the $5,000 to $20,000 range). It’s enough to draw close to 5 million video views on some weeks, with such early standouts as “I’m F–ing Matt Damon” and its response, “I’m F–ing Ben Affleck” — which included cameos from the likes of Cameron Diaz and Harrison Ford — having generated more than 30 million views each over the last three-and-a-half years.

“I think celebrities saw that they could be part of something that was a big deal and they got to be funny. Everybody wants to be funny,” he says, adding that publicists get calls from their clients asking why they weren’t in the videos. That explains how he gathered everyone from Rob Lowe to Sting to Matthew McConaughey for “Handsome Men’s Club,” another gag video about an exclusive fraternity for the industry’s most attractive men, from which he is expelled, shot over several weeks in multiple parts earlier this year.

On this night, Griffin, who has played everyone from Martha Stewart to Justin Bieber in Kimmel videos, had requested that his staff whip up another one for her to do. Before she knew it, she was squeezing herself into a fat suit and wig to play Schwarzenegger’s housekeeper/mistress, Mildred “Patty” Baena. Says the comedian in the green room after the show, “I rarely let someone write for me, but they’ve got this down.”

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The show is over now, and outside Kimmel’s studio, the audience is filing onto buses headed for an advanced screening of Abrams’ Super 8. Instead of relief to have gotten through another show, Kimmel will tell anyone willing to listen that it wasn’t — as the preshow chant suggested — his best show ever.

But to know Kimmel is to know he is never fully satisfied and is always looking to make the next show better. “Fear of failure drives me more than anything,” he acknowledges. “At the end of the day, every day, I have to go onstage in front of a bunch of people and be funny. I work nonstop because I don’t want to go downstairs and bomb. I hate it. I hate it a lot more than I enjoy succeeding.”

The couches in his office are lined with people — visitors, friends, staffers, family — but Kimmel lacks the enthusiasm he displayed on camera for the past hour. As the postshow drinks begin pouring and laughter fills the room, Kimmel’s mind appears to be elsewhere. Probably on the next show.

— Marisa Guthrie contributed to this report.

JIMMY’S GREATEST DIGITAL HITS: Known for his viral videos, Kimmel has seen his sketches on YouTube glean 103 million total views this year

• I’m F–ing Matt Damon: More than 30 million video views
• I’m F–ing Ben Affleck: More than 30 million video views
• Jimmy Surprises Bieber Fan: 31.1 million video views
• The Jersey Shore Saga: Friggin’ Twilight: 6.1 million video views
• 11-Year-Old Girl Interviews Justin Bieber: 5.8 million video views