When he knew he wanted to become a comedian

I was funny from an early age. I remember saying something when I was like, 9, that was legit funny. My family was cool with it. My older brother, Kevin Brennan is a comedian, so he was massively helpful.

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Technically I did win Class Clown senior year of high school but on the voting ballots it said "Funniest" and the Yearbook staff changed it to Class Clown, which I was not at all. I think people voted for me for "funniest" because they knew I did stand up.
When I was a young boy, I studied high math because I was put way ahead in school. So I was doing college when I was 9 years old, I was very good at math, very shy. And then the professor of calculus said "the next theory we're going to learn if A, then A equals A." If A', then A equals A, and he said "what do you think the name of this theory is" and I said "is it the pointless theory?" And he was fantastic to work with.
I farted when I was born and everyone lost it. The real moment would probably be my first play. I was in 5th grade and those laughs felt so goooood, baby.
I was always funny. I grew up around a bunch of funny people. Every time the bus stopped, whoever got off the bus, I would start talking, like, doing what that person was saying and where they’re going, and like a voice for that person. I was doing it loud enough and the whole bus was laughing, and it went on for like a half hour. Then when I got off the bus, the whole bus clapped.
No. I wasn't funny at all. I didn't even suspect that I had a sense of humor until I went to college. And then something kind of changed. I don't know what happened. Perhaps it was meeting new friends and being in a different environment that unleashed something in me. I don't know.

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Feeling like there wasn't a job out there that felt right. I tried a lot of them and it was clear I couldn't fit into society like a normal human being. Get the fuck out of Iowa! Go find your tribe and start living your life the way you secretly wish you could. Stop being afraid of what other people will think of you and do the thing you want to do. Above all, leave Iowa :)
I basically started performing for my mother, going, ‘Love me!’ What drives you to perform is the need for that primal connection. When I was little, my mother was funny with me, and I started to be charming and funny for her, and I learned that by being entertaining, you make a connection with another person.
I didn't plan on getting into comedy, but in high school and grade school I was interested in comedy. I PLAYED CHRISTOPHER ROBIN IN WINNE THE POOH WHEN I WAS IN 3RD GRADE MOTHERFUCKERS. Decided comedy was a real option sophomore year of college. receSs was the crew.
This is how much I wanted to be a comedian and didn’t realize it: I had a paper route for years when I was a kid, and when I was on my route I used to recite George Carlin bits, Richard Pryor, Eddie Murphy — I used to recite his “Hit by a Car” bit word-for-word. I would fantasize about doing it in front of my entire grade in the school auditorium. But I still wasn’t able to make the connection of maybe that means you want to be a comedian. It didn’t seem possible. But I know the exact moment when it seemed possible. I was working in a warehouse with this guy and he was into comedy — first time I’d ever met somebody who was into comedy the way I was. And I used to go over to his house to drin...
I'd love to have a shitty job. I couldn't hold any down. Standup was the only thing I could stick with. I'm an idiot that way. seriously this is the real answer.
I never thought about "being" in comedy when I grew up because I didn't know it was a real job. But looking back, it's the only thing I ever really cared about.
Because I was good at it. And I thought I wanted to be an actress, but I didn't have a passion for it. But the first time I did stand up, I knew it was... the one.