Funnier Than Thou

In my quest to find out what I want to do with my own life, I've often sought counsel and guidance from guys in careers ranging from hedge fund managers to baseball GM's to union steamfitters—people that have found some measure of happiness and success with their respective stations in life.

What's made these interactions worthwhile is that regardless of career, by digging into the nuances of the decisions made by other guys I've always learned something that I could apply to my own career choices.

Recently, I had the pleasure of sitting down with Nathaniel "Than" Bryan, an up-and-coming comic who came to my attention during his time as an eminently competent producer for Opie and Anthony on XM Satellite Radio as well as a cohost of the Than and Sam show, which aired as part of XM's Saturday Night Virus lineup and always made for great listening on weekend road trips.

More than anything else, speaking with Than provided me with keen insight into the fact that so many of life's challenges and decisions almost invariably come attached with an equal number of paradoxes.

Paradox 1: Comedy and Tragedy

The 30-year-old New Canaan, Conn., native graduated with a degree in economics from Middlebury and started out at as an analyst working for Morgan Stanley in Times Square. While the job looked impressive on a business card, he always felt a little out of place and soon found himself searching for something else.

Comedy and tragedy, French absurdist playwright Eugène Ionesco noted, are inseparable. Appropriate of this paradox, one of America's great tragedies ironically paced Than in his pursuit of a career in comedy.

On 9/11, Bryan wasn't near the towers, but he was working in the City. Like anyone working in New York at the time, the event caused Than to do some soul searching.

If this building was on fire and I knew that this was going to be it; would I want to be here in my cubicle?... I never wanted to find myself in a position wondering, "what else could I have done with my life?"

For Than, that what else was readily apparent.

"There came a point at Morgan Stanley where I wasn't interested in my job and spent the day listening to O&A and Ron and Fez and decided that's where I wanted to be—on the radio," he said.

With this goal in mind, he enrolled in the Connecticut School of Broadcasting, graduated and soon found himself on Opie and Anthony's staff. After nine months as an unpaid intern, Than was then brought on hourly and eventually became a salaried employee as associate producer in 2006. During Than's tenure, the show grew to have among the most listeners in America, reaching both a satellite audience that some estimate at a million listeners in addition to a widespread terrestrial radio following in many of America's largest markets.

Paradox 2: Be careful what you wish for…

The next paradox came when Than realized that he finally got what he wished for. In effect, the dog caught the proverbial car and was all of a sudden forced to ponder, what now?

Feeling he couldn't give enough to his comic aspirations while working full time for O&A, Than left the show last May to focus on a career in standup. The classically-trained pianist had always enjoyed performing (although he admits being deathly afraid of recitals) and soon found himself on stage working for laughs.

"I enjoyed it when I would write a line for the guys and it would get a laugh," he said. "However, I would much rather be on stage and get the laugh myself."

Paradox 3: No Laughing Matter

Since leaving the show, Than has worked hard on tuning up his act, highlighting the next paradox: a career focused on being funny is often anything but.

In an ideal day, Than spends two hours watching video of himself and writing and at least a half hour practicing and rehearsing his material. This would be followed at night with a 5-15 minute set where he works on building a comfort level on stage.

"I always strive to be more present on the stage; I want to have a conversation with the audience as opposed to yapping at them," said Than. "There's a delicate balance where I have to incorporate the audience's reactions while at the same time trying not to care, or at least convincing myself that I don't care. Any time the audience thinks you're pandering to them, they tend to clam up. You have to develop a relationship with them, and it's not easy because if you're phony, they really can see through you."

For now, he's fine-tuning his material, hoping to find that joke-telling nirvana where the comic gives the audience no choice but to laugh. "What separates the really good comics is the ability to get a laugh even when they feel like the audience hates their guts," said Than.

I caught Than performing one night in a Times Square club where it was apparent that he knew what he was doing. More than his dry humor—which provided some genuine laughs—it was interesting to see how comfortable he appeared on stage, moving with a sense of purpose and chatting up the audience like a pro.

On the flip side, in exchange for stage time at this particular club, Than had to hand out fliers to pedestrians on the street, something he no longer does on principle.

"(Handing out the fliers) is tough for a number of reasons," said Than. "Instead of getting mentally ready and focused, you're standing outside getting rejected most of the time, and the people sitting in the audience are the same people you were just handing fliers to in Times Square. That doesn't lend itself to a good relationship with the audience."

Than's recently focused on finding organic experiences to hone his presence on stage. Typically, comics spend time on stage at open mics, but this too is often an imperfect laboratory to hone one's craft.

"Typically, there are only other comics in the audience, and it's difficult to get a real, spontaneous moment in front of them," said Than. As he improves and progresses, the young comic hopes to make progress en route to the top of the comedy pyramid :

• Open mics (In New York, there are 20-30 smaller clubs where young comics can work as they get their chops. )
• Guest Spots (performing several times during the week at the good clubs for free; however not doing anything for the clubs, eg. handing out fliers.)
• Paid Spots (playing NYC spots like Caroline's, Comix and Gotham)
• Tour Headliner
• Jerry Seinfeld/Ray Romano/Chris Rock

On the way up, Than's thankful for the support of his wife, family and friends. "Most of them think I'm going to end up back into the business world," said Than. "But we're finally at a point where my loved ones recognize that while this may not work, they're no longer waiting for me to come to my senses."

Than says he's glad he made the leap now, because "You can't be 40 and trying to break into the business," he said, recognizing that the trip to the top of comedy Olympus isn't always lined with laughs.

Paradox 4: An Embarrassment of Riches

Than's experiences working for O&A exposed him to some of the biggest names in standup. "Headliners like Louis CK, Bob Kelly, (Rich) Voss, Patrice (O'Neal), and Jim Norton have all given me terrific advice and opportunities," said Than who considers the high point of his comedic career when he opened for Jim Norton at the Hammerstein Ballroom in front of 2,000 fans. "What I've learned from Jimmy—and from all the best comics—is that they're all incredibly driven. They can't wait to try it again and do it better. "

While working at XM gave Than exposure to these top-line talents—a blessing in virtually every way—in some ways it represents yet another paradox in that it's proven to be an embarrassment of riches in some ways.

"These guys all have strengths I can learn from, and are great to new comics," said Than. "But at the same time, they're all headliners, touring the country; they're not necessarily able to drag me around with them. It's funny to think this way, but the comedians that haven't quite made it to that level yet would be better for providing opportunities around here."

Undeterred, Than plans to continue improving and climbing to the top. He recognizes that his dream is no laughing matter. "I've always known that it's going to take a long time; I never thought it was going to be overnight," he said.

From you're damned if you do, you're damned if you don't to a rolling stone gathers no moss, reflecting on Than's decision and drive brings to mind a million different clichés. I admire his willingness –in the face of a slew of challenges and all the bullcrap life throws in one's path—to chase the dream, and think he's got a genuine chance of making it to the top.

I wish him the best of luck in his endeavors and am eternally grateful for his openness in taking the time to talk with me.



Catch Than at a Touch of Laughter-- a fundraiser for the Touch Foundation-- at New York's Comix Comedy Club (53 W 14th St, just east of 9th Ave) on Thursday, March 5. Call 212-524-2500 for more details.