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.

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 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.

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.

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...[Read more]

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 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.

i once was a caller for a boat tours company in chicago where i would yell at people walking by to take the tour. that sucked!

the last jobs i had were fixing cars and covering football games for a local access tv station. as in driving the mobile van to the field, setting up 3 cameras, teaching depressed grownups and interns how to use them and directing the game from the van and then wanting to kill myself.

I always loved stand up but didn't think it was possible. Hollywood seemed a zillion miles away. It wasn't until I was working at a warehouse and I met a guy who was on my level in stand up, we used to go out drinking and get a buzz going and watch stand up in the clubs together. He said to me one night, "Bill we're funnier than a lot of these guys." And he said one day he'd take a shot of Jack and get up on the stage and do it. And I thought if he could do that, I could too. I was emotionally beat down in my life at that point and just couldn't imagine it. But thank god he said that. I went after it and learned to speak up, instead of keeping quiet.

I had a few jobs when I was young. I worked as a bag boy, a dishwasher, a salad chef, a carpet cleaner and a cardiologist.