Like the title of his first CD Everything’s the Best!, things are going pretty good for Josh Gondelman. A self-described well mannered comedian, Josh is as comfortable in front of a packed house as he is in the classroom.  At just 26 he has a decade of teaching young kids under his belt.  It’s fodder for a style of comedy that’s as accessible as it is funny.

“I try to write what’s true to me.  So if I have a wide appeal I guess it’s because I’m an easy going, easy to relate to person,” explains Gondelman.  “I’m an easy to get along with person I think, and I think that translates to onstage.  I don’t put on a character like someone that’s a jerk.  I’m a pretty polite dude and I try not to put people off or not upset people with my day to day activities.  I apologize for things constantly.”

Gondelman used to describe his style as “some holds barred comedy.” There’s plenty of adult material in Everything’s The Best!  Girlfriends who cut themselves, teaching preschoolers about gay marriage, shopping for morning after pills and racist stereotypes are all on the menu.  But instead of beating people over the head with an expletive-laced shouting frat boy style that seems to be standard fare at open mics across America, Gondelman takes a more real, more nuanced approach.

“It’s not an issue of censorship or consciously trying to be accessible or mainstream,” says Gondelman.  “I try to have my comedy reflect how I feel about things in the world.  I’m just generally a positive guy and that’s what I want people to take away.  George Carlin wanted to speak social truths while making them laugh.  I think my goals at this point are a little less.  I just want people to feel good and like people.”

In The Beginning

Gondelman was a 19-year-old student at Brandeis University in 2004 when he got hooked on standup.  Soon it would take over his life.

“The first couple of years it was like, ‘Oh I’m in college still. I’ll go out once a month or twice a month when I can,’” Josh remembers.  “But then by the end of college homework was a secondary priority.  I was leaving campus to go into Boston and I would go into the city like twice a week to do sets.”

Nearly eight years later, Gondelman is reaping the rewards.  In 2010 he won the Laughing Skull Comedy Festival in Atlanta, an event that draws well over 100 comedians. This past weekend he was back co-headlining with 2011 winner Sam Morril.  The breakthrough win opened a lot of doors.

“It sort of introduced me to the industry side of meeting more bookers and agents and managers and stuff.  It really helped.  It expanded my reach.  I can go more places, talk to more people, so it’s very exciting.”

You know things are going well when your ex-girlfriend’s boyfriend is getting you work with comedy legends.  It happened to Gondelman last year when a phone call connected him with one of his heroes.

“I get a call from my ex-girlfriend’s boyfriend and he’s like, ‘Hey I booked a theater in Massachusetts’ and ‘Would you drive up to Western Mass to open for Steven Wright?’ I was like ‘yes, absolutely, he’s like a legend, a living legend,’” Gondelman gushed.

“I watched his old tonight show set for Johnny Carson.  It was when standup stood out from the old Boston scene in the late 70s early 80s.  It was breathtaking. His use of language is beyond what most people try to do with language jokes.”

Backstage, Gondelman enjoyed one of the perks of success.  There he was, with a respected icon in comedy passing along kind words and wisdom to the next generation.

“He was super nice and low key.  We talked about the Red Sox because we’re both from Boston.  He was just really encouraging and cool.”

The Various Talents of Josh Gondelman

Standup is his main vehicle, but it’s not the only outlet for Gondelman.  Josh is a prolific writer for everything from blogs to a full-on book he’ll be working on in 2012.  He looks to the likes of Patton Oswalt, David Sedaris and Chuck Klosterman for inspiration. There’s also the podcast Two Man Canoe where Gondelman and fellow comedian Dan Boulger (former Boston Comedy Festival winner) hang out with other rising comedians.  But when Gondelman wants that instant feedback, there’s only one fix.

“I think what attracted me about standup is night to night you can be diligent about work and you can show improvement on a night to night basis,” says Gondelman.  “And if you have more than one set in a night, on an hour to hour basis, you can make adjustments and really see your work pay off in almost real time.”

2012 will be even busier for Gondelman.  He’s already booked for SF Sketchfest later this month, and has his eye on Portland’s Bridgetown Comedy Festival in the spring.  When asked about his top goals for the new year, Gondelman tries to focus on things he can control, mainly getting better, and developing new material.  Writing a spec script is also in the works.

“It’s frustrating to me to set goals that are outside myself and then not meet them,” explains Josh.  “If I say I want to be on the Late Show with David Letterman by the end of the year, and then I’m not, it’s not up to me.  It’s not one of those things where if I work hard enough I can make that happen this year.  It’s not necessarily a true thing.”

But if Dave’s bookers come calling, Josh will be there.

“It seems like kind of an old school achievement and old school appeal that I really like.  I like watching the sets that are on Conan where they’re more anything goes.  But I think my style of comedy is more  a traditional guy talking into a microphone.  And so there’s something that just appeals to me of the four minute or five minute Letterman set that’s just you come out, you tell jokes and then it’s over.  So I think it has that prestige to it.”

Gondelman recently moved from Boston to New York City.  When he’s not working on his word economy at three-minute open mic sessions, he’s trying to catch some of his favorite headliners.

“I love Pete Holmes’ new album Impregnated with Wonder.  He’s right in line with the point of view that I’m really excited about expressing.  I feel like he’s a more advanced and complex version of that.  And Gary Gulman.  I watched his last CD recording a couple months ago in New York and it was great.  His joke writing and technique are terrific.  Myq Kaplan is always a guy who has an insane work ethic and has so much integrity onstage just trying to really present who he is.  He’s not trying to dumb it down or smooth it out for people.”

New York is also bringing new projects for Gondelman.  He’s working with Emily Heller, Erin Judge and George Gordon to write and produce a new comedy show, so look for that in the months ahead.  For now, go to iTunes to find his album Everything’s the Best!  The album was created in conjunction with Rooftop Comedy Productions and features a cover shot of Josh fully enthralled on the glorious sands of the New England coast.

“We went up to New Hampshire with my friend Bill, who is a really really great photographer.  I think the humor was I had it recorded and I just wanted to share my CD and my attitude and that was what the excitement was mostly about.”

You can follow Josh Gondelman on twitter, facebook, his blog Josh on the Road and the podcast Two Man Canoe.  And of course his website at joshgondelman.com.

For more comedy news and exclusive interviews visit our AmericasComedy.com Facebook fan page and follow us on Twitter @AmericasComedy!