The War for Late Night (21 page)

But the demands of radio helped define his work ethic. With no staff and no resources, Kimmel had to put together hours of material for the daily schedule on his own. He arrived each morning terrified because he was making $25,000 and supporting a family of four. If he got fired, he would have to move them all again, because there really was no other radio station in any of these towns that would want what he did. So he planned and wrote and somehow produced five or six hours of content a day. Every waking hour had to be devoted to gathering material for the following day. He didn’t even have time to relax and watch Letterman for an hour—not when he had to be up and at the station by five a.m.

When Kimmel finally landed at K-Rock (KROQ-FM) in LA, he found a niche that stabilized his peripatetic career, becoming “Jimmy the Sports Guy” for a popular morning drive team, Kevin and the Bean. Finally somewhat secure, he sought out side gigs for extra money. Among others, he won a spot as a writer for a would-be game show that the legendary former programmer for multiple networks Fred Silverman was putting together.

“Gossip” had the rather preposterous premise of asking contestants to watch a series of bizarre events involving celebrities, only one of which was real. Kimmel thought the show had no shot at ever seeing the light of a TV screen—they were going to shoot it six months in advance and expect the real gossip items either to be still unknown or still relevant? But it was a paying job, so he didn’t care.

At the time of the initial run-throughs, “Gossip” had no host, so the producer asked Kimmel to stand in for a day. Within a few minutes of taking charge of the stage, Kimmel got it into his head that he could surely lead this stupid thing—a suggestion the producer dismissed when Kimmel offered it. But Jimmy raised his energy level and performed in the run-through as though the show belonged to him. Silverman was sitting in the empty audience seats sipping a glass of iced tea. This kid suddenly got his attention; he watched for a while and then called out:

“Cancel the host auditions! This guy’s the host!”

Silverman brought the show to a series of meetings with potential buyers, with Jimmy fronting the presentations. A young executive with ABCʹs production studio named Michael Davies sat in on one of them. Davies, an Englishman who knew from British television that game shows were not the lowest form of TV life, as most American producers believed, didn’t care at all for “Gossip.” But he recognized a game-show host when he saw one.

From that moment on, Michael Davies became Jimmy Kimmel’s unofficial career placement officer. Convinced of his talent, Davies laid a series of potential projects out for Kimmel, who shocked Davies by rejecting them all. Jimmy, just hitting thirty, needed money desperately, but he knew the next move was a crucial one for him. He couldn’t jump into television in some throwaway slice of processed cheese. That was a ticket back to radio, maybe forever.

Then Davies showed up with an offbeat project called
Win Ben Stein’s Money
. The premise was a spin on a quiz show in which every week contestants played against Stein, the dry and wry conservative commentator, writer, and actor, for (supposedly) his own money. Davies set up Kimmel to audition, and no one needed to see any other candidates. During the presentation for network buyers, Kimmel lit up the stage, providing a comic edge that made the show distinctive. Comedy Central outbid other networks. Kimmel suddenly had a television career.

He didn’t exactly fit the usual physical prerequisites of a TV star. Not really overweight but always slightly puffy, Kimmel looked less like a leading man than a relaxed-fit jeans model. Medium height, often rumpled around the edges, with a thatch of black hair that always trailed off this way or that and hooded eyes that made him look perpetually sleepy (perhaps because he actually suffered from narcolepsy), Jimmy didn’t figure to win a lot of face roles from casting directors—or style points from the fashion police. But he made up for those shortcomings with spirit. Outgoing, boisterous, and far, far smarter than a first impression might convey, Kimmel exuded a sense of fun that never seemed faked. He plainly enjoyed what he was doing, which seemed to consist largely of taking any and every opportunity to spread the fun around. He also had that Vegas penchant for daring, which could lead to both breakthrough comic ideas and occasional transgressions in taste. Mainly he seemed on television to be exactly who he was in life: the wiseass kid grown up. Deeply into sports and music (he even played bass clarinet), he was a guy’s guy, up for anything that had a shot to be either laugh-your-ass-off funny or just outrageous enough to disturb the universe in some way.

The Davies connection came into play again two years later when Kimmel and his pal Adam Carolla devised a show aimed to be “the anti-Oprah.” Kimmel had been told by a producer that he would never appeal to women, so he and Carolla, another radio-based comic, planned a show to appeal to the most basic (and debased) instincts of guys. Davies loved
The Man Show
and pushed it to the ABC programming division. But the network was appalled. “It was the most poorly received pilot ever,” Davies recalled.

Given the British executive’s classy deportment and accent—not to mention suits—his advocacy for this project, as well as for an apparently rude character like Kimmel, may have seemed unexpected. But Davies, who went on to import and then produce for ABC the biggest game-show hit of all time,
Who Wants to Be a Millionaire?
, simply got Kimmel. Once
The Man Show
was on Comedy Central and a hit, he never lost contact with his discovery, and that connection would pay off again, bigger than ever, for Jimmy.

In the meantime Kimmel climbed another step up on his own. Playing off his sports-guy persona on K-Rock, Kimmel worked a deal with Fox Sports to provide a comedy sketch for the network’s pregame show every Sunday. While making half-serious picks on the games, Kimmel found ways to tweak both the NFL and the roundtable of ex-jocks that populated the show. The bumptious crew, led by Terry Bradshaw, quickly came to sneer at Kimmel’s weekly presence, but the quarter hour when he appeared demonstrated a clear ratings uptick.

Kimmel, whose deal with Fox was freelance, got a call out of the blue from CBS Sports, the other network with a Sunday NFL show. Surprised but intrigued, Kimmel quietly flew to New York to meet with Sean McManus, the president of the division. McManus, son of the legendary ABC sportscaster Jim McKay, pitched Jimmy hard about coming on as a regular on
The NFL Today
. When Kimmel got back to LA, still mulling the CBS offer, Leslie Moonves, the capo of capos at CBS, asked to meet with him, a gesture that signaled an overture of real substance. After explaining how ardently CBS wanted him for the football package, and all the great things Jimmy could do on the Sunday football show, Les, who had clearly done his homework, came at Kimmel in the place where his deepest dreams resided.

“I know you love Letterman,” Moonves told Jimmy, surprising him with that little bit of research. “Maybe we could put something else on the table for you down the road.”

Moonves told Kimmel that he didn’t much like what Craig Kilborn was doing in the 12:35 show. (Moonves seemed to have a different take on late-night talent than the experts at Worldwide Pants.) He tried to tempt Kimmel by suggesting that Kilborn was not going to be around forever. And if Jimmy was in the CBS family when that 12:35 show opened up, it would certainly be something Les and the network would consider for Jimmy.

If Moonves meant to flatter Kimmel, he succeeded—maybe a little too well. Kimmel had a lifetime of reasons to want to be in the CBS lineup behind Letterman. Instead, the gauzy promise that Moonves had floated failed to send even a shiver of anticipation up his spine. To the contrary, here he was, a total stranger to CBS, and the network boss had a plan that sounded like he was taking candy away from one baby and offering it to another. Something about it put Kimmel off, and he declined.

A few other offers drifted in: the funny neighbor/boyfriend/bartender in that year’s crop of pedestrian sitcoms. Jimmy talked them over with his agent—the same James Dixon who worked with Jon Stewart—and both agreed that they were not the right fit, not the direction they wanted for Jimmy’s career. Then Fox came at them with an idea for what Jimmy really wanted: a late-night show. There was one catch. Because Fox had such a dismal history in late night, it couldn’t just launch a new entry with a virtual unknown as the star. Fox offered to start Jimmy off at a local station the company owned in Minnesota. If he worked out there, they could expand station by station until he was ready for the network.

Kimmel and Dixon thought the Fox offer was insulting, not to mention borderline insane. How was this better than trying a sitcom?

He had no reason to mention it to Jimmy, but about the same time Dixon found himself in the middle of a late-night chess game going on elsewhere. In the wake of the failed mission to land David Letterman, ABC had in 2003 made contact about a possible post-
Nightline
slot for Stewart.
The Daily Show
had elevated Jon’s profile immensely by that point. Still, this would be a network show, which meant more cachet—and more money. Jon was at least interested enough to listen.

The man at ABC plotting the late-night moves was Lloyd Braun, the same executive who had led the charge to win Letterman. Like everyone else in television, Braun was hugely impressed with how Stewart had transformed
The Daily Show
into a nightly must-see for news (and comedy) junkies. The circumstance seemed like it might be a simple game of pitch and catch. ABC had only to toss the offer out there in a formal way, Stewart would pull it in, and they would be in business.

But Braun hesitated. As great as Jon was in this new show, it was still cable. And some might argue that it was, of all things,
too
smart. Would Jon’s scintillating wit and scalpel-sharp puncturing of politics and media play at a network level? Was he too New York and LA?

And given the public strikeout with Dave, would anyone who could be identified as a “usual suspect” in late night escape a label of second choice? Would a totally new name be better? In his late forties, Braun was a onetime entertainment lawyer who had climbed up the Hollywood ladder from management company to studio head to the top of ABCʹs entertainment division, and he could not afford to make a choice that flopped. With ABC’s prime time near moribund, he had to make this move work.

Roiled by uncertainty, Lloyd went to play golf at the Riviera Club with a friend whose views he had come to trust. Braun waited until midround to bring the issue up. As they stepped onto the ninth green, Braun laid out his late-night dilemma and hit his playing partner with the question he had been waiting with:

“Knowing it could be anyone, someone I’ve never heard of—someone without a name—and knowing I have the luxury of offering the midnight show, if you could pick anyone, anyone at all, who would it be?”

With no hesitation at all, Michael Davies said, “I know the guy.”

By the end of the day, Davies had sent Braun a cassette with Kimmel highlights on it, including an appearance with Letterman. Braun found himself charmed. He needed to learn more about this guy quickly, but there was a troublesome problem. Braun couldn’t simply ask Jimmy’s agent for material, because that agent, Dixon, also represented Stewart, and Braun did not want to spook a guy who was still his first choice. It was an awkward situation, even for the frequently conflicted business of showbiz agenting.

So Braun accumulated the material he needed elsewhere. Even amid the depths of taste the comedy sometimes reached on
The Man Show
, Braun thought he detected a real intelligence at work. Kimmel seemed much cleverer than the material. He needed to talk to him.

The feint was that ABC might consider Kimmel for a show at one a.m. That was better than a show in Minneapolis, so Jimmy went to lunch with Braun. He knocked Lloyd’s socks off with his “wicked smarts” and his blue-collar charm.

At home with a stack of tapes, Braun tried to weigh the options. He watched fifteen minutes of Stewart followed by fifteen minutes of Kimmel—back and forth, most of the night. He kept reaching the same conclusion: Both great; Kimmel had a more everyman appeal. Braun surprised himself with that conclusion, so much so that he asked a question out loud: “Am I really going to pass on Jon Stewart?” The answer came when he invited Kimmel to his office and broke the news: ABC wanted Jimmy Kimmel to host its midnight show.

The news stunned Kimmel—this time in a good way. The offer also put James Dixon in a potentially touchy position, because ABC had chosen one of his guys over another. When Braun called Jon to let him know, Stewart did not hold back his displeasure—he was especially consternated by how ABC had gone about the process, jerking him around. Remarkably, considering how personally hosts had taken such tugs-of-war over late-night shows in the past, Stewart blamed Kimmel not at all. He praised Kimmel’s talent, saying he was happy for him to get this chance, “even though I was disappointed for myself.”

Perhaps more remarkably, Stewart never wavered in his continued allegiance to James Dixon. One deal that didn’t happen was hardly going to disarrange what had become the closest and most important professional partnership of Jon’s life (Dixon’s as well). One thing it did mean, though: James Dixon, now with two clients installed as hosts—and other assorted late-night players on his roster, including Winstead and Smithberg, the creators of
The Daily Show
, and Stephen Colbert, then emerging as the hottest comedy correspondent on that show—was positioning himself as a kingmaker for late night. Dixon, a savvy, aggressive Cornell graduate seemingly escaped from a Damon Runyon tale, spoke like a New York cabdriver from a 1940s movie—both in accent and colorfully descriptive vocabulary. A contemporary of Stewart in age and a match in physical stature, Dixon engendered an unusual degree of loyalty and actual, identifiable fondness from his otherwise cynical comic clients. He routinely called them all “Baby Doll,” to a point where that became his own nickname. It occasionally turned heads when a client like Kimmel addressed the darkhaired, always moving, often smoking Dixon as “Baby Doll.”