If switching from music to comedy was all part of the plan

I never had a plan. I just sort've ambled along, doing exactly what I wanted every day of my life. It turned out well. I could easily be sleeping in a ditch now. I'd say always follow your passions. Even if you fail, you've had a great time trying.

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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.
Comedy has been tremendous for me. I enjoy making people laugh, and to be able to make a living at it is pretty spectacular. I was in college, and kind of floundering, as a lot of young people do. I thought I wanted to be an accountant, and after taking some accounting classes, my eyes would roll so far up into the back of my head that I thought ‘I don’t think I can hang with this for the rest of my life.’ Nothing wrong with that profession. My dad was an accountant, and many wonderful people are accountants. It just wasn’t for me. So I switched majors to communication and theater arts, which was a combined major, and it was in that world that I hit on the idea of being a stand-up comedian.
The Adam Sandler movie, The Longest Yard came into town to shoot and I met Adam Sandler, Nick Swardson and a bunch of other comedians. They came to Swig, the nightclub where I was go-go dancing in Santé Fe and they saw a drag queen, a stripper and Annie Lederman. The minute I saw them in person and I saw that they weren’t just these giants you see on the screen, I realized that comedy was what I really wanted to do.
The ceiling for comedy in New Orleans is about a foot-high, so you have to army crawl your way through it—it’s that low. New York was no question. I went to film school here a year before, and I just fell in love with the city then, so I came back. In New York you can get a lot of stage time [as a comic], and I needed and wanted that. It was the worst transition ever. I moved here with $800, blew through that in about two days, got an apartment in Crown Heights, got mugged three times in a year, my landlord died of AIDS, and the first day I got into my apartment, there was a pigeon in it, just flying around. So it was pretty rough. I got a job as the file clerk at the film school filing pap...

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Well, it didn't seem like I had much of a choice. I don't think that - you know, I don't think that my hand would have cooperated with my brain if my brain was telling my hand to write something it didn't really want to write. But I remember when there was some interference from NBC with "Seinfeld" when we first started doing it. And fortunately I didn't have a family at the time. So it's - it was very easy for me to say to them, no, I'm quitting; I'm not going to do that. I don't want to do that, and I can't do it. And for me, it wasn't a big deal to just pack up and go home. Like I said, I hadn't - I didn't have a family. It's much harder. That's the first piece of advice I'll give anybod...
you gotta deal with like a decade worth of bullshit before you start seeing the fruits of your labor. Just avoid negative people and keep writing and perfecting your set. Throw out jokes that don't work. Keep the ones that do work.
Go to the open mic and befriend whoever intimidates you the most and just work as hard as they do. It’s what helped me. I always had this group of people I could call and be like, should I stay at home and write? And they’d be like, you’re bullshitting yourself. Stop avoiding it and go to the mic.
getting paid does NOT make you any better at standup, trust me. i wish it did. it's all about getting as much stage time as possible. it took me 2 years - my first gig, i got paid $20 and i drove 8 hours to do it. worth it. advice: get onstage, however possible. there are no shortcuts. you need to put in the time.
Start a show. Host the show. at a bar or any space. then you have guaranteed stage time and you do other comics favors by giving them spots so then they will give you spots on their shows. also hang out a lot at comedy clubs.
some things don't change. You need to get on stage as much as possible and vary your stage experience as much as possible and not quit and take care of yourself and always question why you say the things you say and enjoy yourself. The context of history and technology just is what it is.
Best advice was when I asked Paul Reiser, "How do you get started in comedy?" I asked him that when I was in college. He said, "Well. You've just got to do it."
Find other people who make you laugh and spend as much time with them as you can. They'll make you better and keep you motivated.