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Dues unpaid, Net jock goes Hollywood

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Times Staff Writer

OK, we’ll stipulate you’re a talented, funny writer, and somebody in late-night TV should hire you for his staff. But how to make it happen?

You might do it old-style, paying your dues in heckler-infested comedy clubs and lugging dog-eared spec scripts to endless appointments. Or you could take a lesson from Bill Simmons, who made his own breaks on the Internet and rode victoriously into Hollywood a couple of months ago.

Simmons, a 32-year-old sports columnist from Boston without a shred of TV experience, has come west to join the writing staff of “Jimmy Kimmel Live,” ABC’s heavily promoted venture into late-night comedy. Kimmel’s show, which premieres after the Super Bowl on Sunday, will occupy the 12:05 a.m. weeknight slot formerly held by “Politically Incorrect.”

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Resentful outsiders in the comedy-writing community can be inspired by Simmons’ tale. Or they may brandish it as an example of the lunacy that transpires when a network turns over a coveted time slot to a marginally known entertainer like Kimmel, whose last job was hosting the girl-ogling “The Man Show” on Comedy Central.

Simmons started his sports column six years ago on a Boston Web site limited to America Online subscribers. He eventually hooked up with another local site, and over the next few years developed a following by creatively blending his addictions to local sports teams and pop culture. In mid-2001, espn.go.com, which regarded Simmons as a natural for its young male readers, hired him to write three columns a week.

There, he blossomed. Speaking as “The Sports Guy” rather than a guru, writing out of his apartment rather than a stadium press box, reveling in the Internet’s lack of space limitations, he invented hip new styles of fandom.

There were the 10 rules for women who wanted to watch sports on TV with their boyfriends. (Rule 3: “When your boyfriend’s buddy calls to discuss a game in progress, don’t shake your head and definitely don’t mutter spine-crumbling comments like ‘God, I hate your voice when you’re talking to your friends.’ Needless phone calls are a crucial part of the viewing experience. They remind us we aren’t the only ones wasting our Sundays.”) There were the “13 Levels of Losing” to help you categorize heartbreak. (Example: The third-worst level, “The Guillotine,” occurs when your team is hanging tough, but you know a tragic moment is coming, and you’re proved right. “These are the games when people end up whipping their remote controls against a wall.”)

Simmons was so consumed by the 1996 young-men-on-the-make film “Swingers” that he built his annual NFL awards column around 37 quotes from the movie, each illustrating a different virtue. He created an “Unintentional Comedy” scale to numerically rate the most glaring absurdities of athletes and celebs. (Level 86 on the scale of 100 included “Any Wimbledon interview where Bud Collins tried to say something foreign to a non-American champion like ‘danke shein.’ ”)

The thrice-weekly column had been on espn.go.com less than a year when Entertainment Weekly put it on its “It” list of “who’s hot and getting hotter,” proclaiming Simmons “destination reading for anyone who worships at the twin altars of pop culture and sports.”

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Which was when Kimmel came calling.

To appreciate the symmetry of that moment, let’s go back to the mid-1980s, when a couple of teenage boys in New England and Las Vegas would stay up until 1:30 a.m. to watch “Late Night With David Letterman.” The boy in New England -- Simmons -- fantasized about writing for Dave. The boy in Las Vegas -- Kimmel -- fantasized about being Dave.

Kimmel went into radio (because that’s how Dave began his career) and eventually broke into TV. Simmons, who grew up in Boston and then moved to Connecticut with his mother after his parents divorced, became a sportswriter in college at Holy Cross, where he had his own column on the student paper. “This was the one thing that I thought I could do better than other people.”

After graduating he was tempted to drive to L.A. to try to break into comedy writing but didn’t have the nerve to go by himself. So he got a master’s degree in journalism at Boston University, then took a reporting job on Boston’s tabloid, the Herald, hoping to rise to a columnist but instead enduring “three long, horrible years. You’re fetching coffee for some 300-pound copy editor and everybody’s fighting with each other. I got really discouraged.”

He quit, tended bar for a year, then decided to give a column a shot on the Internet. Even a few thousand hits a day can do wonders for a young man’s ego. And there was the thrill of e-mails from readers who were getting attached. “People would tell me they’d take printouts of the column into the bathroom.”

Kimmel, whose gigs include Fox’s pro football pregame show, became a fan once Simmons moved to espn.go.com. Then, last April, Simmons offered a minute-by-minute dissection of a pay-per-view roast for Shaquille O’Neal, bludgeoning all the roasters except Kimmel for being too timid to taunt the guest of honor. Kimmel, who noted that Shaq’s rapping was worse than his free-throwing, “gets an A-minus, bonus points for nearly saving the roast and my undying respect and admiration,” Simmons wrote.

Within hours, Kimmel e-mailed his thanks and the two kindled a friendship. All the while, ABC was offering Kimmel his own show to follow “Nightline.” Once the deal was sealed, Kimmel asked Simmons to join his writing staff. Simmons balked, unwilling to give up the column he’d nurtured so long. Kimmel flew Simmons and his fiancee to L.A. in September to court them.

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Simmons, raised in a culture where the Boston Celtics-Lakers rivalry was the ultimate struggle between good and evil, felt the SoCal stereotypes melt away. “All you hear about L.A. are the girls

Because ESPN and ABC both have Disney as a corporate parent, Simmons was able to broker a compromise in which he’ll write his Internet column once a week.

Nevertheless, his announcement in November that he was cutting back left many fans crestfallen.

Kimmel, who went so far as to phone Simmons’ mother to offer reassurance that the writer would be in good hands here, says he was struck by the closeness of the two men’s sensibilities.

“When he talks about [the 1979 basketball movie] ‘Fast Break’ staring Gabe Kaplan, I can’t believe anybody outside my circle of friends knows that. He’s not trying to be funny by guessing what people laugh at. He’s writing about what’s funny to him.”

Simmons has already received the Easterner’s official welcome to L.A. -- a jaywalking ticket. He’s wrestled with the difference between working solo without an editor and the endless filtering of ideas that goes on with nine co-writers on the sixth floor of a Hollywood Boulevard production office. He’s gained confidence. A few weeks ago he acknowledged, “I’m probably the show’s biggest gamble.”

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Kimmel, who emphasizes he is less interested in scripted joke-writing than the ability to turn reality on its ear, agrees. The show’s party line is that the 50-ish Letterman and Leno have lost the edge that made them funny, that this show will have a looser, spontaneous feel, like a talk-radio show.

“Right now,” says Simmons, “I feel like there’s not a talk show for someone like me. Barring Jimmy getting caught in a minivan with 13 transvestites, I feel this is gonna work.”

“And just for the record,” he added several sentences later, “the transvestite thing will never happen.”

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