You know him, you love him, it’s Neal Brennan! Writer, director, co-creator for, obviously, “Chappelle’s Show.” Director for “Inside Amy Schumer” and “New Girl” amongst others. Has his own Comedy Central “The Half Hour,” host of The Champs podcast along with Moshe Kasher. The list can go on, so I’ll stop there. His views, observations and overall style is conversational, relatable and most of all interesting. A crazy funny comedian who is certainly one of the greats. We talked to Neal about his podcast and his upcoming stand-up special, so enjoy!

Serial Optimist: Neal! Thank you so much for talking with us, we really appreciate it! First question, what is currently your favorite stand-up special/DVD to watch or one you laugh the hardest at?

Neal Brennan: I can’t say I’m currently watching any stand-up specials right this second, but I did enjoy Sommore’s Showtime special a few months ago. Had “chandelier” in the title. I’d never seen her before, which is rare/odd, but she was great.

SO: Sommore’s Chandelier Status! Not sure if you know this, but when you Google your name, President Obama shows up in the images with a teardrop tattoo. Just wanted you to know that. Also, how excited were you when you met President Obama and the First Lady?

Neal: I was very excited to meet the President, but I’d donated money to his campaign, so I sort of felt like…it was the least he could do…

SO: President Obama definitely owed you one. Where did you grow up and what was it like being the youngest of 10 siblings? Were you treated more like a protected baby of the group or one that had to learn for yourself?

Neal: I grew up in Chicago and Philadelphia. Growing up the youngest of 10 was pretty crazy. I’ve been arguing with adults (my siblings) since I was like, 7 years old. And not just any adults. These were angry Irish adults. I don’t remember any punches being pulled or advantages being given. But I was little, so I don’t know…

SO: When your brother, Kevin, started doing comedy, did that awaken something in you or do you feel like you would have chosen comedy as a career anyway?

Neal: It definitely was like, “wait, you can do comedy as a job?” Not sure if I would have picked it without him, but again, maybe I would have. That’s some “Sliding Doors” shit.

SO: I used to love “All That” as a kid, what was it like writing for the show? Do you have any particular sketches you liked the most? Would it hold up as being funny today?

Neal: Writing for the show was interesting because it was the first writer’s room I was ever in where we were re-writing as a group. Definitely taught me to speak up and trust my instincts. Too many times, I’d want to pitch something…stay silent…and then somebody else would pitch it. Having said that, I was very unsuccessful at that show, but they liked having me around I think. They used to call me “The Boy” because I was only 21 or 22 at the time. They liked abusing me. One time, the Exec Producer jokingly said to me: “I should have fired you when I had the chance.” He wasn’t kidding.

SO: That sounds like a pretty jerky EP! Onto moving your talents elsewhere… obviously, writing/directing/producing/co-creating “Chappelle’s Show” came with a lot of ups and downs for you. Can you name a moment from one up and one down?

Neal: Up would be the whole show. I liked the process: writing, directing, editing, the live part. I really loved it. Dave’s an unbelievably funny guy. Gonna let you guess what the down was, but it rhymes with Mafrica.

SO: I think I guessed it. You made The Goods: Live Hard, Sell Hard after making “Chappelle’s Show.” You’ve also directed an ep of “New Girl” and I think, every ep of “Inside Amy Schumer.” What’s the comparison to directing movies versus television?

Neal: Movies are grander, with (in my experience) more heavy weight chefs in the kitchen: the studio, the producers, the writers. All of them get to weigh in and you have to listen to all of them because they hired you. With TV, it’s a way smaller scale, with only a few people (Dave Chappelle, Amy Schumer/Jessi Klein, Liz Merriwether) weighing in. I prefer that. Because whether the show succeeds or fails, [it’s] going to have a huge impact on their life. The Goods doesn’t do well – and Paramount is fine. I almost feel like whoever has the most at stake should have the most power. Or at least the funniest person. Which in TV, it is.

SO: “Inside Amy Schumer” is so good, but to me that format seems so difficult to put together for a director. Incorporating Amy’s standup show to be played throughout an entire season, the wonderful cutaways of her with the music Questlove did, I guess my question is how much of a challenge is it putting all that together?

Neal: I don’t put it together. I just direct some of the filmed sketches. Amy and Jessi Klein put it together. But honestly, that’s way easier than writing it. The victory of the show is in the writing. Coming up with sketches and stand-up bits. The rest is just hitting buttons on a machine more or less.

SO: Shifting to your podcast, I’ve listened to every episode since you started The Champs along with Moshe Kasher—who I love—and, formerly, DJ Douggpound. Not sure if you’ll appreciate that or think of me as a crazy fan. But… I really like how you guys usually have a black guest or some kind of minority because that’s often lacking in most of them. Why did you want to get into the podcast game?

Neal: I wanted to get into the podcast game because I like talking and Joe Rogan said it very much helped with his live shows. So, two years later…here we are…

Neal On Conan

SO: Sounds like a good reason. The dysfunctional nature of the podcast between you and Moshe is one of the best qualities of the show. What made you want to keep the verbal fights in? BTW, when you guys discussed who would win in a physical fight, I kind of think Moshe would just edge you for the win.

Neal: Me and Moshe legitimately don’t get along. It’s not that we don’t like each other. We just have opposing viewpoints on almost everything and we’re both very confident in ourselves. So if you like our opposition, that’s probably why. Because that shit is real, son.

I would physically beat Moshe in a fight 100 times out of 100. He has zero athletic ability and moderate strength at best. Also, he has zero Irish rage. There’s a reason Notre Dame named themselves the Fighting Irish and not the Fighting Jews.

SO: You and Moshe have such confidence in your fighting abilities. I guess we’ll never truly know who’d win. Back to you, you’re hilarious every time I see you perform, so I was excited to hear you taped an hour special for Comedy Central. Are you happy with how it turned out? How soon will we expect to see your stand-up special?

Neal: I am very happy. All I know is that it will air sometime in the fall, which I’m happy about because I need time to write new material.

SO: Cool! Color me excited! Are there any new things you have planned that you’d like people to know about?

Neal: I’m gonna be a dad! (Kidding. My GF just broke up with me.)

SO: No! Neal! Now I’m sad for you and this is the last question! You like to stick with either women/dating or race as stand-up subjects. How do you consistently talk about it in new ways? You pull it off so well!

Neal: I don’t consciously stick to it. Although the name of my hour is, Women and Black Dudes. I just write what I’m interested in. Chappelle’s wife Elaine said to him one time, “All you and Neal talk about is work and girls.” (As it turned out, work=racial comedy)

SO: Thank you Neal! We’re excited about your special and hope you find a lady soon!

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SO Note: That was the fantastic Neal Brennan everybody! Follow him on Twitter @nealbrennan and check his website nealbrennan.com for tour dates, videos and that good stuff. And of course, guys, look out for his stand-up special, Women and Black Dudes, this fall on Comedy Central.