Paul F. Tompkins is in pain. Not the kind of psychological suffering that plagued him for much of his adult life, but palpable, physical pain. Right now every tooth in Tompkins' mouth is emitting a sharp, incessant throbbing, periodically building to a crescendo so great that he involuntarily yelps.

At the behest of CBS, Tompkins spent an hour this morning holding perfectly still in a Beverly Hills dentist's chair, his mouth propped open by a device straight out of "A Clockwork Orange," while a laser burned off years of accumulated plaque and nicotine.

"As I was sitting there, I was mad at CBS," says Tompkins, 39. "I kept thinking, 'What's wrong with my teeth?'"

Then another dentist made a mold of the prominent gap between Tompkins' two front teeth so that a piece of orthodontia called a "flipper," which he would be required to wear on set, could be fashioned. CBS said it was either make his teeth TV presentable, or lose the role on a pilot.

Dealing with networks is nothing new to Tompkins. He is a two-time Emmy-nominated writer for his work on the HBO programs "Mr. Show with Bob and David," and "Real Time with Bill Maher," and a regular commentator on both VH1's "Best Week Ever," and MSNBC's "Countdown with Keith Olbermann." He is in the upcoming Paul Thomas Anderson film "There Will Be Blood" for Paramount, and has appeared in a handful of other features, including the hit "Anchorman: The Legend of
Ron Burgundy," and "Tenacious D: In the Pick of Destiny." As one of the most respected and popular alternative comedians, Tompkins is flown all over the country — he never learned to drive — to perform to sold-out comedy club crowds.

Tonight, he is the headlining comedian at the Upright Citizens Brigade Theatre in Hollywood, and is expected to speak for at least half an hour.

Tompkins already owns a flipper — its creation also mandated by a television studio a few years ago. He brought the archaic, inorganic tooth with him to the dentist's office, and, after sliding it into place, the dentist laughed and laughed, even calling in a colleague to share the joke.

"It's not homemade," says Tompkins later that night to a delighted audience as the events are transformed into a 13-minute story. "It's not like, 'I don't need you guys. I made this in my basement.'"

Tompkins, looking newly slim, runs a hand through his tousled auburn hair as the laughter builds.

"I didn't bring this in thinking, 'Wait until they get a load of me.'"

The Realization

Fifteen years ago, at the age of 24, Tompkins left his home in Philadelphia and found exactly what he was looking for in the back of a coffee shop on Vermont Avenue in Los Feliz.

Tompkins had discovered The Onyx Cafe, and, by extension, the burgeoning alternative comedy scene of the 1990s that was breaking all the rules of the comedy clubs he had spent so much time in. Comedians like Mary Lynn Rajskub (now playing the oft-beleaguered Chloe O'Brian on FOX's "24"), Doug Benson (currently contributing to VH1's "Best Week Ever"), and Greg Behrendt (co-author of the bestselling "He's Just Not That Into You: The No-Excuses Truth to Understanding Guys") were glancing at notebooks, recounting auditions that failed, and mining their lives for material. They may not have succeeded every time, but the style was daring and honest in a way that appealed to Tompkins.

"It was tremendously inspiring," says Tompkins of the alternative scene, "and got me to a deeper place. It was the kind of thing I wanted to do, but was afraid to."

The First Los Angeles Friend

Before Tompkins headed west, Adam McKay, a friend since college who would go on to direct "Talladega Nights: The Ballad of Ricky Bobby" in 2006, suggested he meet up with Jay Johnston, another comedian who was also moving to Los Angeles. Johnston called Tompkins, but before the two got a chance to chat, they ran into each other at a show in Los Angeles.

"That was a big moment," says Tompkins of meeting Johnston. "We hit it off right away, and started writing together within a week of knowing each other. He was my first Los Angeles friend."

The two brainstormed a series of sketches, including one in which Johnston attempts to sell Tompkins a magic carpet. They haggle over the price of the carpet, take it for a test flight, and promptly become marooned. The sketches were quickly cobbled together for a show called "The Skates," that, at the urging of McKay, was attended by Bob Odenkirk and David Cross, the creative masterminds behind HBO's "Mr. Show with Bob and David."

"Their show was, and remains," Cross says of "The Skates," "one of the funniest sketch shows I've ever seen. I knew immediately that they were people I wanted to work with."

A year later, when HBO ordered a second season of "Mr. Show with Bob and David," Johnston and Tompkins were hired as writer/performers, and worked on the program until its cancellation three years later. "Mr. Show with Bob and David" became the most critically lauded sketch show since "Monty Python's Flying Circus," and today, a decade after its demise, is enjoying a healthy cult status.

"It really felt like," Tompkins says of the offer, "'This is happening so fast. I've only been here for two years and now I've been hired to write on this show with these two guys that I respect enormously.'"

Tompkins' professional life was coming together. His personal life, however, was teetering on ruin.

Self-Loathing

In addition to leaving Philadelphia for a shot at stardom, Tompkins also followed a girl.

"I was head over heels in love with her," says Tompkins, "and in love with all these girls who did not love me back."

Tompkins was convinced that if they returned his adoration, all of the self-loathing, insecurities, and self-recrimination he was carrying around would fall away, and he would be happy.

With his love life in shambles, doubts began creeping into his professional career.

Tompkins convinced himself that his peers on "Mr. Show with Bob and David" did not think he was funny enough to work with them. Unbeknownst to him, most of the writers — save for Odenkirk who had already worked on "Saturday Night Live" and "The Ben Stiller Show" — had similar doubts.

"Paul has a very unique voice," says Odenkirk in a recent interview, "and maybe he didn't feel that strong on 'Mr. Show' because I think the best, purest place for his voice is in his monologue."

Tompkins' doubts only grew as time went on. It wasn't until years later, while recording the commentaries for the "Mr. Show with Bob and David" DVDs, that he finally felt comfortable around the other writers.

"When I look back on it," says Tompkins, as he sips a cup of tea in a coffee shop near his Hollywood apartment, "I know that there was a lot of fun, and a lot of laughing, but I also cringe in embarrassment at the guy that I was. I was punishing myself for no reason and didn't realize it. I wished I could have pointed a finger at somebody else
and said, 'You're the reason I feel like I don't like myself.'"

Critical Reception

"I think most of us that do stand-up," says Tompkins, "have a common ground in that we start out from a place of pain — and wanting to be liked and loved and heard."

As the fifth of six children, in a house that had a revolving door of older siblings coming and going, the idea of harnessing attention appealed to Tompkins. He is quick to point out that his parents — a former secretary at a piano tuning company and a retired rail road break inspector — were not neglectful, but that he was a very needy
child.

On July 11, 1986, a month after he graduated high school, Tompkins performed stand-up for the first time and discovered what he wanted to do for the rest of his life.

His family has been dutifully supportive of his career, though they ask more about the celebrities his profession has allowed him to meet than anything he has done.

Recently, Tompkins' relatives expressed an interest in seeing "Tenacious D: In the Pick of Destiny" with him while he was home for Thanksgiving. Tompkins and his girlfriend bought a ticket for the film, but his family paid to see a different movie that began hours earlier. Then, 15 minutes into the film, as he cowered in his seat, the Tompkins clan loudly sneaked in to the movie theater and gave a half-hearted cheer when Paul's name graced the screen.

"I would like them to get it," says Tompkins, "and be the funniest person they've ever seen, but at a certain point I had to accept that I am not my family's favorite comedian."

These Days

Last year, Tompkins stopped smoking — one month shy of a 20 year addiction — and started working out. He figured it was time for a physical as well.

"So you're changing your life?" the doctor said matter-of-factly to Tompkins after learning of his recent changes.

"Wow, I really am," Tompkins thought to himself. The realization washed over him like a wave, and all the things that he never thought he could do flashed through his mind.

On stage, Tompkins recently admitted he would marry an elliptical machine if possible. "I think, legitimately, that that is what the far right is afraid of," Tompkins told a laughing audience. He visits a local YMCA nearly every day, and is in better shape now than he has ever been.

And he's found love — the mature kind, with his girlfriend of over a year. Arguments no longer lead to a period of avoidance, but to thoroughly discussed solutions that have allowed him to better understand himself and the relationship.

The past has stopped being a source of pain and regret, but one of learning. And in 2002, Tompkins began regularly attending therapy sessions.

"It's great to see how comfortable and strong he's become," says Odenkirk. "I'm very happy for him artistically."

During the taping of last year's Comedy Central Presents special, Tompkins, clad in a navy blue, double-breasted, pinstripe suit, felt more alive and in control than he has in a long time. As he calmly walked around the stage, a broad smile etched on his face, the
audience's attention never wavered. Tompkins considers the performance not only a highlight of his career, but of his life.

"I'm not going to say that I absolutely have it all figured out," Tompkins says through slightly whiter teeth, "but I'm making the effort."