"I didn't really have an end goal," Brennan says. "I guess I always wanted to be a popular comedian. I’ve always thought that’s the coolest thing, even when I’m directing movies. I was always kind of thinking that being a popular comedian, that would be cool to me. Having said that, you can do more than be a popular comedian. I still direct commercials. I'm about to do a TV show for Netflix that I can’t really talk about. I do a lot of stuff and then I still work with people like Dave [Chappelle], Chris [Rock] and Ellen DeGeneres."
Now he's reached the point in his career where he's become a popular comedian and it's given him something he's been wanting a long time.
"Time is the thing I need the most of," Brennan says. "I'm lucky to have made decent money over the years, but now I'm most interested in having a good first-person experience. That’s the fun part about stand-up. The doing of it, the point of view from me onstage is amazing and the feeling, all the serotonin
Brennan is more than just a great comedian with a national tour that includes a stop at the House of Blues on Saturday, Oct. 20. He's also one of the most prolific TV comedy writers in the business, one who's shaped some of the medium's most influential and beloved programs. He found his start in the clubs as the doorman of the Boston Comedy Club trying to sell jokes to the comics, including comedian Dave Chappelle, according to a 2014 profile of Brennan on the Vulture blog.
He broke into television writing in the '90s on shows like MTV's dating game show Singled Out and Nickelodeon's sketch comedy show All That. He teamed up with Chappelle to write and direct the cult stoner comedy Half Baked and created the massive TV hit Chappelle's Show that lasted for almost three seasons before its star suddenly left the show and country in the middle of its final season. He went on to direct other popular TV comedies like The Mindy Project and Comedy Central's latest sketch show success Inside Amy Schumer, stand-up specials for Michelle Wolf and Al Madrigal and the 2009 film The Goods: Live Hard, Sell Hard produced by Adam McKay and Will Ferrell.
Since then, he's found another route in comedy through stand-up that led to the critically acclaimed specials Women and Black Dudes for Comedy Central and 3 Mics for Netflix in which he mixed one-liners, his stand-up act and some brutally honest stories about his alcoholic father and struggle to find effective medical treatment for his clinical depression.
"That was just a good use of material," Brennan says. "We did an episode of Chappelle's Show that we called our garbage episode, with all the stuff we never used and Dave said, 'We use the whole pig. We eat the snout.' That was me eating the snout."
The special also gave him the opportunity to jump in his own spotlight and be known for more than just that guy who wrote for Chappelle's show before he bailed on the set.
"It's fun to do it because people know me more now and they're really invested," Brennan says. "It's like, 'We're here for you specifically.' That was kind of the point with 3 Mics was letting people know me better than just Dave's buddy. I was happy to be Dave's buddy. That's just how I was known so now it's cool to be known for that and other stuff. I'm just happy to make your life better."
Of course, he hasn't strayed from Chappelle after their groundbreaking comedy show. He says they've been cool with each other over the past 10 years and even presented an award together at the 2018 Emmys during which Neal joked about their partnership, a line that was hard to find a writer to help with, for obvious reasons.
"It’s more work than you think than to just walk out there and talk," he says. "Dave called me and asked if I wanted to do this and I was like, Yeah, and then it was a matter of what are we gonna say?"
Brennan says he and The Tonight Show Starring Jimmy Fallon announcer and longtime Saturday Night Live writer Steve Higgins came up with something they could say onstage after a laborious process over a single joke.
"All the SNL writers were afraid to write for us, which I get," Brennan says. "I am too. I pushed through it, but it was still intimidating to write."
Brennan says his work isn't about creating a legacy for himself or his work. He knows legacies don't last even among the greats and that getting caught up in the stress of making a TV show or a movie can create a great deal of stress. So whether he's working behind the camera on another TV project or touring to do his own
"When Charlie Murphy died, I went to his funeral and all I thought was, 'I hope he had fun,'" he says. "It wasn’t even about his legacy. I don’t buy any of that stuff because I don’t think anyone talks about anyone a month after they