When Neal Brennan‘s episode of The Half Hour debuts on Comedy Central this Friday night, it may very well be the first time you’ve ever seen that much of Brennan’s stand-up comedy. At least, as delivered by Brennan himself.

But you’re certainly familiar with his comedy. Brennan co-wrote Half Baked with Dave Chappelle, then followed that up by co-creating and co-writing Chappelle’s Show with him. Brennan also wrote and directed sketches for the first season of HBO’s Funny or Die Presents, directed the 2009 film The Goods, and wrote material for SNL’s Seth Meyers to present at both the White House Correspondents Dinner and at the ESPYs.

Now he gets a chance to shine solo. After taking questions from fans on Comedy Central’s Tumblr yesterday, Brennan hopped on the phone with me to talk about his comedy career.

Since you were just on Tumblr, and I know you’re active on Twitter — how much do you use social media and technology to advance your jokes as well as your career? “Just for individual jokes. In some ways, I’m just competitive. Not even competitive. It’s just an addiction. If Daddy doesn’t get 100 ReTweets a day, Daddy gets sick…Daddy needs a hot one. You have to prove every day that you’re funny. It’s the only profession where you have to do that every day.” Brennan said the feeling comes whether you’re live onstage, doing a full weekend of great sets, but if you bomb, then you need to get right back up and perform again to regain your mojo. Same thing applies online. “That’s what Twitter is for. You show the fucking kids that you still got it.”

“If I link to an article, and it gets a lot of reads, I feel like I’m on the pulse,” Brennan jokes. “That New York Times article. I get it! I know what the people want.”

Speaking of news, here’s a clip from Brennan’s half-hour on Comedy Central, in which he describes how British reporters and anchors can make any story sound sadder. Roll it.

You say in your routine that you watch CNN. Where exactly do you get your news from these days? newyorktimes.com and guardian.co.uk and a website called Truthdig which is lefty and independent. And you know, I had this stuff going at Huffington Post which, if given the choice between the front page and the entertainment bar, I found myself quickly hitting the entertainment bar, so I took it off my bookmarks, because I’d go, ‘What is J’Lo’s butt doing?’ When I should be clicking on ‘What Are Michelle Obama’s Arms Doing?'” Brennan also acknowledges he’s just as likely to be lulled into clicking on “news” items such as “How Many Calories are in a Candy Bar?” “I cannot trust myself on Huffington Post,” he says. “It’s not them. It’s me.”

Your routine also mentions the “It Gets Better” videos for gay teens. How would you envision a campaign like that, but for would-be comedians? Could you envision one? “I actually pitched one. (For) the Oscars a couple of years ago, I pitched an ‘It Gets Better video for people who lost, which would have been funny, which is exactly why they didn’t use it.” This was the year James Franco and Anne Hathaway co-hosted. Brennan was hired for the writing staff to help them. “Jordan Rubin tricked me into it. Me and (Brian) Posehn pitched two days of jokes, and they didn’t use any of it. When (The Academy Awards) aired, I was shitting on it (via Twitter), and landing a lot of hot jokes, and then people were saying you have to follow @nealbrennan, and the credits roll and my name was first alphabetically.”

So if the Oscars wasn’t your highlight, what was your best side gig for comedy writing: The White House Correspondents Dinner, the ESPYs, or a third thing I failed to mention? “The Correspondents Dinner, just because Seth (Meyers) and I are really good friends, and it was such fun in terms of it couldn’t have gone better, and it was a fun night in terms of getting respect for it from politicians and journalists. And with Chappelle’s Show — they were like, ‘You’re that guy?!’ It’s like the cleanest win ever.” He also got to work with other Saturday Night Live writers he liked on that. Although he did enjoy working with professional athletes on ESPYs videos, too. “But for the most part, the correspondents dinner. Because I got to yell at the president, basically. ‘Yo, Seth, tell Obama this!’ And we got to go out to the French embassy afterward, where it was glamorous and people are pretty. And there weren’t a lot of celebrities, show biz people. Like out here in Los Angeles. You can find yourself stuck at a party with people going, ‘What are you up to? What are you up to?’ There wasn’t that overall appraisal that goes on in L.A., there were maybe only 15 celebrities there.”

Is that what you imagined your life would be like back when you were younger, writing for kids shows such as All That or Kenan and Kel“This is exactly the thing I was thinking! Ha. No. I never really planned on anything…

“When I was in high school, I was at the Improv in New York watching my brother (Kevin). And Robin Williams came in in 1988 with Dennis Miller. And that was the fucking coolest thing ever. It was like they were The Super Friends or something. And then older, you end up hanging out with people like Chappelle and (Dave) Attell, I guess it’s analogous…the fun part is hanging out with people who are talented and good dudes, and funny in a way — that’s not to say, they’re funny as I am, but they’re fucking funny. Whenever I talk to a girl after a show who says she’s funny, I say ‘Really? Because I hung out with Dave Chappelle for 12 years. He’s funny…Lemme guess. You can quote movies?'”

You mention your brother, Kevin Brennan, who started in stand-up several years before you did. Was he that direct of an influence of you choosing a career in comedy? Or did you try other lines of work first? “Honestly? It completely affected my being in comedy. Literally when I was in high school, my brother’s best friend was Attell. in 1987, my first year of high school, I was elected senator in my class. And Attell did a joke that the senator was shot. A really funny joke. I’d see Ray Romano — Kevin used to give him a ride home all the time. It made it seem more real, more attainable.

“I started out as a writer…and now he’s doing more writing and I’m doing more stand-up. He wrote for Norm’s (Macdonald’s) show and Tom Papa’s pilot. I can go to the (Comedy) Cellar (in NYC) and do spots and not worry about taking spots from him.”

You don’t find too many brothers who are in the stand-up arena separately. There are twin brothers who are duos, but not stand-ups. There’s Tony Rock with Chris, and now the younger brother, Jordan Rock. And there’s the Regans, Brian and Dennis. Or you have one brother getting in, like Charlie Murphy, only after his brother, Eddie Murphy, has stopped performing stand-up. “It is a rare thing. Because it’s your brother’s thing. When I was young, I said there was no way I was going to seek the attention of drunken strangers like that. And then the older I got, I needed the attention of drunken strangers.”

Brennan said he also shied away from stand-up for a while after the abrupt ending of Chappelle’s Show. He wanted to avoid dealing with hecklers or people pestering him about Chappelle, asking, “Where is he? Why did you fuck him over?”

“And then in ’07, I was like, ‘Fuck it. I want to do it every night.’ I took three months off to do the (Jeremy) Piven movie (The Goods), but otherwise, I’ve been doing stand-up every night.”

You don’t shy away from racial language or topics — did you always talk about race in your stand-up, or was that something that came out of your working relationship with Chappelle and writing sketches for that show? “I’ve always been interested in race. Before I even met too many black people. I was interested in race as a topic of human depravity. Just a real massive human error. You’re better than they are because of melanin? We’re dividing people by color? That’s stupid. And the thing about comedy, it’s just about the most integrated thing on the planet. I was at a show the other night, in Santa Monica — I do a show every Sunday at The Westside Theater to work out new material — and it was three balck comics and three white comics and they were all hugging to say goodbye. Where else do you that kind of friendship? The biggest stumbling block to integration is just access. People just don’t know. White people don’t have access to knowing a lot of black people. And vice versa. They’re just like us for the most part.
You know, I say the n word a bunch onstage. It kills the hardest when I do it in black rooms. It’s only in white rooms where they get upset. And I think in some ways, people come up to me after the show and say, ‘I dug your stuff’…and I’m not saying it as part of crowd work. You’ve seen my act. So i have an advantage in terms of pedigree.”

Brennan mentions that a few other white stand-up comedians have felt freer about racial language because they’re putting it into proper contexts.

Right. Like in a past Louis CK special, he jokes about how TV anchors and reporters, by saying “the n word,” all they’re really doing is passing the buck and putting the actual word in your head to make you think it. “Louis says it because he’s got a way to make it work. And before I say it, I say shit about white people and I don’t even do it by design. I just do it because that’s how the joke goes. There’s nothing nefarious.”

Greg Giraldo, Neal Brennan and Dave Chappelle, circa 1997(ish)

There just might be something nefarious about this photo from 1997 or so that you shared online yesterday featuring you standing between the late Greg Giraldo and Chappelle. Why were you all dressed up like that, anyhow? Please say it was a wedding or something legitimate. “It was some…like Manny from the Cellar, some charity thing. I think Attell called the picture a self-destruction sandwich. Which I think is very funny.”

Before or after you tune into Neal Brennan’s half-hour stand-up on The Half Hour, check out this backstage interview he gave to Comedy Central, in which he addresses his first times onstage.

If you’re in the Los Angeles area, you can see Neal Brennan and Friends live most Sundays at M.I.’s Westside Comedy Theater in Santa Monica. You can be anywhere with access to a computer or iTunes to listen to The Champs Podcast, which Brennan hosts with Moshe Kasher and DJ Douggpound. A new episode of The Champs Podcast is out today, with guest Pras from The Fugees.