Comedian Neal Brennan Headlines Water Street Tavern

Let’s face it: writer, comedian and director Neal Brennan is not a household name. But nearly everyone instantly recognizes the project he is most associated with: Chappelle’s Show.

Brennan co-created Chappelle’s Show with his then-pal Dave Chappelle. The show debuted on Comedy Central in 2003, ran for two seasons and was a huge hit. Then Chappelle abruptly left under puzzling circumstances. A truncated third season, dubbed “The Lost Episodes” was put together with existing material after the show’s namesake quit.

Brennan will headline Kent’s Water Street Tavern  tonight at 9:30 p.m. Also on the bill for the free show are Mike Polk Jr., Bill Squire and Anthony Savatt.

Brennan didn’t get serious about doing stand-up until about four years ago.

“I did a little bit while I was doing Chappelle’s Show but not much, because I was a little busy,” he said. As soon as he started, people were asking why he wasn’t headlining shows.

“I didn’t have the act, really,” Brennan explained. “So I just waited until I had an act that was good enough to headline with, and that happened a few months ago.”

Brennan is not a fan of the pay structure at established comedy clubs, so he went the do-it-yourself route.

“I have a lot of followers on Twitter, so I asked ‘where should I go?’ and people just flooded my inbox with suggestions,” Brennan said. "So basically it came out because of the magic of social media.”

Brennan’s show reflects his passions. “I’m basically interested in three or four things – politics, girls, race and technology, so those are the things I tend to write jokes about,” he said.

As a writer, Brennan has had a number of high-profile gigs recently. He wrote for the Academy Awards and ESPN’s ESPY Awards, but by far the biggest job was writing for the White House Correspondents’ Dinner with his friend Seth Meyers this past May.

“That was fun because I’m interested in politics, I follow it,” Brennan said. “So it was fun to write jokes about these people I know about anyway. We wrote some jokes about Obama, and the great thing about that is that I knew he was going to hear them.”

Brennan used the opportunity to tell the president some things he wanted to say to him.

“One of the jokes of mine that Seth did was, ‘None of these Republicans can beat you, but you know who could? Barack Obama in 2008. You would’ve loved the dude. So full of promise,’” Brennan said with a laugh.

“And that's really how I feel,” he added. “I think it’s how a lot of people feel.”

Brennan shared one joke that didn’t make the cut for the White House affair, another one directed at the president. “I think of your re-election campaign the same way I think of a troubled cousin,” he said. “I wish you all the luck in the world, buddy, but I’m not giving you money again.”

In his act, Brennan tells of meeting the president and Michelle Obama.

“I had heard Michelle was a fan of Chappelle’s Show,” he explained. “So I walk up to the president and I go ‘Hey man,’ which I’m pretty sure you shouldn’t call him. ‘My name is Neal Brennan and I co-created Chappelle’s Show with Dave.’ And the president said, ‘Oh wow, we love that show. That’s got to be one of the greatest shows of all time.’ That felt pretty good.”

The president then called to his wife. “So Michelle comes over and says ‘We were so upset when it went off the air,’” Brennan said. “And I leaned in and said ‘how do you think I felt?’ So we actually all laughed together.”

Before working on the groundbreaking sketch comedy show, Brennan worked with Chappelle on the stoner comedy film Half-Baked.  Released in 1998 in the same week that Titanic came out, it tanked at the box office. But the DVD release gave the movie a second life, and it now enjoys a bit of a cult following.

I asked Brennan about the secret to the film’s popularity. “Because it’s about weed and it’s something to do when you smoke weed,” he said. “It’s that simple.”

Brennan will finish his tour with appearances at Montreal’s Just for Laughs Festival at the end of the month. He's also been shooting some sketches that he’s going to post on his YouTube channel. “I like the idea of doing all this stuff independently,” he said.

Brennan has a few other opportunities he can’t reveal, but for now he likes being on the road. “I’m really interested in doing stand-up right now,” he said.

Given its size and no cover policy, the has presented an impressive roster of fine comedians over the years, including Nick DiPaolo, T.J. Miller, Sebastian Maniscalco and John Caparulo.

Owner Mike Beder wants the laughs to continue. "We're thrilled to be bringing in a comedian with the resume the Neal has,” Beder said. “He's been doing stand-up for a relatively brief time, so this is really a great opportunity to see someone on his way up. Hopefully he remembers us when he’s really big!”