The Middle With Greg Fitzsimmons

Greg Fitzsimmons has won four Emmy Awards, has his own show on Sirius/XM, and has over 50 TV appearances. He's a regular on Howard Stern, Letterman, Conan, and seemingly everything that's ever aired on VH1. His podcast is wildly successful, his book "Dear Mrs. Fitzsimmons" did incredibly well, and he's about to host a new series on the Speed Channel called "Pumped." But all that and he's not a household name.

"I have made it to the middle in show business and I really like it here," Fitzsimmons said. "I'm not sure that more money or fame would bring me more happiness."

Fitzsimmons' happiness comes in part from the career he spent so many years building up. Growing up "obsessed" with standup, his first appearance was at a talent show his senior year of high school.

"There were drugs involved that night," Fitzsimmons remembered about his routine bashing the faculty. "The principal unplugged my microphone half way through."

After the standard demeaning rise ("I once had a woman vomit on me after I followed a comedian dressed up as a clam," Fitzsimmons said.), Fitzsimmons landed a gig hosting Idiot Savants, a game show on MTV that lasted from December 1996 til April 1997.

But that same year, Fitzsimmons landed a sitcom deal, a show on the USA Network, and a number of other TV appearances. The next decade and a half was a steady climb, much of it centered around his long-term relationship with The Howard Stern Show.

"Stern is like required listening for everybody in show business," Fitzsimmons said about the man who gave him his own show. "You cannot explain how someone gets as successful as him, but being near it gives you a confidence that you should go out and do it your own way."

The other part of Fitzsimmons' happiness comes from his family. Fitzsimmons even sent his mother his first Emmy.

"I think she has dinner with it every night," Fitzsimmons said.

But it was Fitzsimmons' father, radio personality Bob Fitzsimmons, that gave him the advice that would help shape him.

"My father told me when I first started that standup is exciting and I should pursue it, but that writing would be the thing that would give me power over my career," Fitzsimmons said. "I never have to take a road gig or a writing gig I don't want because I always have the ability to play one against the other."

Fitzsimmons standup also reflects his writing ability. Much of his set is made up of short and to-the-point perfectly structured jokes.

"I'm not saying [the TSA] was intense at the screening," Fitzsimmons set up during one of his Letterman appearances. "But tomorrow night the guy who frisked me is introducing me to his parents."

Writing for shows like "Ellen" and the Emmy Awards themselves also allow Fitzsimmons to spend time at home with his wife and kids. And to obtain a kind of happiness we all seek.

"Irish parents will try to off-set their low self-esteem by producing successful children so nobody can look down on them," Fitzsimmons only half joked. "My dad was really proud of me. It was a nice thing."

While many stand-ups fill their lives with regret and a desperate desire to achieve whatever is next, Fitzsimmons is content with his "middle." Well, almost content.

"I make a great living doing exactly what I want and have a lot of choices at any given time," Fitzsimmons said. "I would, at some point however, like to do blow in a Porsche with Paulie Shore."

Christian Finnegan’s Humble Beginnings

Christian Finnegan is a regular on “Are We There Yet,” a show with 44 episodes already under its belt and entering its third season on TBS this fall. But talk to him and he comes off like the average working comedian.

“Right now, I’m able to pay my rent and go on the occasional vacation. If I want to order an appetizer, I order an appetizer,” said Finnegan about his success. “Next year, who can say?”

Finnegan credits his wife for his abilities, the only plug he gave me was for his Twitter (@ChristFinnegan – a joke about the hubristic nature of his name), and is even humble about his remarkable weight loss. While many people would throw that in the face of anyone who’d listen (and even some who wouldn’t), Finnegan doesn’t even mention it in his act.

“I don’t talk about it onstage,” Finnegan said of dropping a startling 88 pounds in under a year. “I’ve found that there is nothing less funny than actual accomplishment.”

Which are two words I’d use when discussing Finnegan: funny and accomplishment. A former writer and guest on “Tough Crowd with Colin Quinn,” Finnegan has been on “The Late Late Show,” “Last Call with Carson Daly,” “Countdown with Keith Olbermann,” and dozens more. He was a series regular on “Best Week Ever,” had roles in movies like “Knight and Day,” and has had two very successful albums. But when I asked Finnegan when he turned pro, his answer was, “any day now.”

Even when it comes to “Chad,” his iconic character on the “Mad Real World” sketch on “Chappelle’s Show,” Finnegan cites luck and not his obvious talent.

“How cool is that?” Finnegan asked about of having “Chappelle’s Show” on his resume. “I’ve always felt like a guy in the stands who caught a home run ball.”

Finnegan first started his journey towards turning a hobby into a career in 1997 at an open mic in NYC in “a room full of wacko poets, musicians, drug-addicted ranters and wannabe cult leaders.” And it was these early days of getting knocked around that helped him stay grounded.

Finnegan’s first big goal was to perform on a show called “Eating It,” the most popular live standup show in New York at the time. He finally got his spot the same night that Wanda Sykes dropped by.

“The show went great and I walked out that night foolishly thinking that Wanda Sykes and I were now ‘peers’,” Finnegan said, before explaining that his day job at the time was to dress up like a Christmas elf and take Polaroids at corporate holiday parties.

The next day, Finnegan put on his costume and snapped photos at a party at Caroline’s on Broadway, the biggest comedy club in New York. The featured entertainment that night was Wanda Sykes.

“As I stood there in my green tights and rubber pointy shoes watching her absolutely destroy,” said Finnegan, “I realized maybe Ms. Sykes and I weren’t peers after all.”

Maybe that’s why Finnegan’s comedy is so relatable. Even when he’s a television star, he still manages to be the everyman, going through the same daily humiliations we all face.

“There is no such thing as having ‘made it,’ there is only ‘making it.’” Finnegan said. “A good comedian never stops feeling demeaned.”

The Brighter Side of Myq Kaplan

I asked Myq Kaplan if he could tell me the smartest thing he'd done for his career.

"The smartest thing I ever did," Myq said, "was answer this question humbly."

I'd argue that the smartest thing he ever did was long before he became a comedian - to channel the teasing that many intelligent kids receive into a whip-smart and bankable sense of humor.

Kaplan has gone from making his TV debut on Live at Gotham to sets on The Tonight Show, The Late Late Show, and Comedy Central Presents to almost winning Last Comic Standing in under three years.

"Blowing up quickly comes as the result of many years of not blowing up quickly," Kaplan said of his overnight success that was nine years in the making. "Put yourself out there as much as possible to create the right-place-right-time phenomenon that is more statistically likely to occur the more places you are, and the more time you spend there."

Kaplan's professional right-place-right-time journey started in Boston in 2002, and continues today in New York. While Kaplan can kill in a coffee shop, he's equally as comfortable in a club full of tourists. Both cities have a big nerd-comedy scene, but Kaplan can play both the alternative rooms and the mainstream clubs.

"I prefer dork," Kaplan said, in response to the eternal nerd-dork debate. "Even though the definition of nerd is probably "someone who deliberates over what differentiates a nerd and a dork."

Nerd vs Dork aside, there are two main types of smart comedy. The first is a show like "Frasier," where the audience has to be smart to get many of the jokes. The second is a show like "The Colbert Report" where anyone of average intelligence gets the jokes, but the smarter the audience is, the funnier the show gets.

Kaplan has developed squarely into that second category. His jokes are intelligent, yet accessible. And there's enough funny in his act that you'll still be laughing even if you miss a few of his quicker tags. And there are plenty.

This is a guy who helped me write the best tag I had during a set on the Late Late Show even before he had been on TV himself. This is a guy who is getting such a rabid fan following that his CD ("Vegan Mind Meld") sells an increasing number of copies each month it's out. This is a guy who, when he was still banging around Boston in 2006, impressed me so much on a comedy message board that I hired him a few weeks later.

His intelligence, his relevance, and his patience were all fueled by the same thing many of us faced as children: other people's ignorance.

"I am pretty happy," Kaplan said, when asked about the bullying he received as a kid. "If I had a time machine that could go back and make my childhood different without destroying the universe or creating parallel dimensions or creating any negative effects whatsoever (the most boring time machine movie in history, or in future), I don't know that I would."

I hope not. Because then we'd be left with one less comedian smart enough to tell a good time travel joke.

The Evolution of Doug Benson

Doug Benson's "The Benson Interruption" is comedy progress, and not just in format. A new spin on the tired comedy showcase, the show is simultaneously classic and contemporary, and hilariously different. Just like Benson himself.

The show was born as a live performance in Los Angeles, moved to a 6-episode run on Comedy Central, and now lives on as a successful podcast. Like it's creator, the Benson Interruption is constantly evolving.

"The idea comes from the funny things the comedians standing in the back of the room say," Benson explained. "Surprisingly, all of my comedian friends embraced the idea and love doing the show. Or at least they pretend to like it."

Benson is best known as the guy from Best Week Ever, or Last Comic Standing, or Super High Me, or Doug Loves Movies. The point is that whatever iteration they know, people know him.

"Without any one of those," Benson said, "there might be 25% less people at each of my live shows."

Simultaneously a comic's comic and a draw, Benson is a rarity. His cleverness plays to the back of the room he's so fond of, but he's also cultivated an incredibly loyal fan base over the 26 years he's been on stage.

"My television debut wasn't until '89 or so," Benson said. "I'm not a big fan of any of my early appearances, because back then there was a lot of stand-up on TV, so you'd get to be on a lot of shows even though you hadn't completely found your voice. I may still be looking for my voice, for all I know."

26 years in, and Benson is still searching for the perfect joke. Not because he needs to; regularly selling out clubs and getting a ton of TV time would be enough for most comics. Benson pushes himself further because he wants to.

Benson's ever evolving voice will be on display on his fourth album in as many years, "Potty Mouth," which will be released on August 30th.

Four albums in four years, and none of them a slacker's effort. Benson' prolific nature fuels his popularity; his draw is so strong because of his relentless ability to stay current. How many 26-year comedy veterans have mastered Twitter? How many comedians who appeared on A&E's Evening at the Improv also have successful podcasts? How many comedians on VH1's talking head shows actually love the 80s because that's when their careers started?

Benson doesn't just love movies and love the 80s – he was an extra in Blade Runner and Fast Times at Ridgemont High. I asked him if he used the films as credits as a young comic.

"Didn't even cross my mind to do that," Benson said, ever evolving. "That would be a pretty cool way to introduce me now. I'll tell the emcee to say those movies at my next show."

Marc Maron and His Implausible Garage

Three years ago, Marc Maron was broke, twice divorced, and thinking of quitting. Not the quitting the business – quitting life.

"I thought about suicide a lot," Maron recalled in his trademark neurotic way. "Not because I really wanted to kill myself. I just found it relaxing to know that I could if I had to."

But three days ago, Maron was confident, successful, and coming off one of the better keynote speeches in Montreal Comedy Festival history. What a difference 20 million downloads make.

That's how many listeners his critically acclaimed podcast "WTF" has earned in two years. It's the second most popular podcast in the world, and I can't have a conversation after a show without an audience member telling me I should listen to it.

Of course I listen to it. It'd honest, raw, and brilliantly entertaining even if it weren't about standup comedy. Telling a comedian that they should listen to WTF is like telling a doctor they should consider medical school. And according to Maron, the podcast has a healing agent to it, too. At the very least, it does for him.

"I started to understand who I was by talking to other comics and sharing it with you. I started to laugh at things again I was excited to be alive," Maron said. "Doing the podcast and listening to comics was saving my life. I realized that is what comedy can do for people."

In 2004, Maron was a guest on my own short-lived radio show, and I was beyond intimidated by how sharp he was. In 2005, I was a guest on his shorter-lived Air America morning show, where he took me to task on air for my ability to market my comedy, hinting I might be all smoke and mirrors. In 2006, I used that marketing ability to help him deal with the world of MySpace, and he made me deal with his anger and frustration when, like life, his MySpace didn't work out the way he'd hoped.

In 2010, I ran into Maron on the subway. When I gave him an enthusiastic hello, it was as if Maron barely knew who I was – odd after we'd spent years chatting in clubs and on the air. But just a week later, he walked up to me at a party and said his own enthusiastic hello, asking how I was doing with genuine interest behind the question.

And that's Maron – a person that has always been on the brink of both unbridled success and complete breakdown. In a life riddled with failed projects and failed marriages, you never knew which Maron you were going to get.

Myspace was a microcosm of the entertainment industry. MySpace was built for a young, hip demographic and filled with booms and busts, and with no real place for an uneasy voice of candid reason like Marc Maron.

But Myspace's brief success led to the launch of YouTube. And YouTube's wild success led to the democratization of entertainment on the internet. And the democratization of entertainment on the internet led to talent like Maron seeing the medium as a serious channel for creativity. And Maron's podcast let to him finally finding an outlet in an industry that generally ignored his tortured genius for the better part of a quarter century.

"I started doing a podcast in that very garage where I was planning my own demise," Maron said, almost choking on the relief of his own emotion. "I know my place in show business now. It's in my garage."