Daniel Tosh described his stand-up act to us as "insanely condescending and sarcastic." We'd add that he has lightning-quick wit that comes with ease. If you've seen him on YouTube or his Comedy Central special, you know that he is naturally honest and unguarded, irreverent without going out of his way to push people's buttons. This Saturday he's headlining his first theater show in New York at Town Hall. He talked with us about winning a Razzie for a movie he refuses to watch, Dave Chappelle's taste in women and why people always mistakenly quote to him, "Always bet on black."

Happy Spring Break. Oh thank you, I can't wait to get to Cancun.

I was told you aren't supposed to go to Mexico this year. That's right, at least mainland Mexico. I assume the Baja Peninsula is at least a little safer. That's true, we aren't supposed to go to Mexico. That's sad. Although I like the idea of being sold into a sex slave ring. That ever happen to young guys?

It almost happened to me once, but I dodged it. The travel would have been nice, but who wants to date a Pharaoh?

Do you have any plans for your coming into New York? Maybe I'll pop in and see Mr. Fallon, see how that show's going.

So far, so good I think. The other night they had Public Enemy on with The Roots playing behind them. That sounds nice. I can't believe the Roots signed up for that gig.

When I heard that, I started to really think the show had a chance. Yeah, for sure. That's when I wished I hadn't of said no to that taxi driver movie with Queen Latifah.

I don't know if you're joking or not. I am. Although I did get a Razzie for being part of The Love Guru. I take great pride in that. Still haven't seen that movie, but I know it's bad.

You didn't go to the premiere? Not only did I not go to the premiere, I have a copy of it in my house and I've still never seen it. I know it's so bad. But worse than seeing the movie was that I read the script, and thought, “This is awful.” and they said they had a part for me, and it was like, “Oh! Thank you!”

You perform a lot at colleges. Do you ever get yourself into any strange predicaments with the undergrads? No, I refuse to socialize in any way. There was a time when I used to play colleges, that I'd hear the words, “Let's go out tonight,” and I'd think “Genius!” But that little notoriety that you have after you finish a show wears off awfully quickly when you're just another asshole at their frat party.

I imagine it goes really quickly from “that guy who just performed tonight” to “that guy who's still here.” It's a fine line for us. So no, I don't, nothing too exciting, you know? Usually the shows now are pretty uneventful when it comes to “oh I can't believe that happened.” Most people that come and see me already have an idea of what kind of comedy I do, so I'm not ruffling too many feathers.

When did that transition take place? That the audiences really knew what they were in store for? Yesterday—recently, ever since Comedy Central started airing my last special a bunch. That definitely helped. So yeah, just in the past few years.

Did you feel with the special airing that you had a pressure to do jokes, whereas in the past you had a clean slate and could do any material you wanted? I don't do any of my old stuff, I don't care what they want. It's just so weird to do jokes that people already know the end to. Friends of mine, peers, will sometimes do an encore with old stuff, and let people yell out the end. But for me, it's boring, so I don't want to do it, and also, I don't remember a lot of those jokes. You record them and they live forever, but to be honest, I couldn't get through half those jokes. So I just do what I want, regardless. I don't worry too much about that stuff. If they want to see those jokes, they can steal them off the internet like normal people. I mean everything's on YouTube, so I don't need to hawk it or retell it.

You don't remember the jokes when they're called for? You know, I thrive on pressure—actually, that's not true. I froze last week on The Tonight Show.

What happened? I forgot my material. But it was the worst time during my set too, because it was my last joke. So I was in the middle of it, and it was fine, and I just froze. And I just kept talking. You could tell I had no idea what I was saying, and thankfully they chopped like twenty seconds of me panicking out of the show.

Did Jay say anything? Yeah, he came up to me and said “Hey, what happened?” And I just said “I don't know.” It was kinda weird, my timing was thrown off because people were clapping at a joke that I had never heard people clap at before. So I was thinking “why are they clapping here?” and before I know it my mind is just wandering. But they fixed it and everybody was none the wiser, unless you know the bit. But he couldn't have been nicer about it, and I've done the show many many times, so I'm not panicked that they're not going to have me back.

In meeting other comedians, which comedian made you the most nervous when you met them? At the top of the spectrum, David Letterman was ridiculous. But then there's always friends of mine now that I'd looked up to so much and now that they're friends it's a little awkward in our conversations—like Louis CK and Dave Attell and a lot of those guys. Even Dave Chapelle, I used to work with him when I was really young. They're all super nice, and they all have different levels of social retardation.

What I've heard about Dave Chappelle is that he tries to make everyone as comfortable as could be. Yeah, although that's not recent talk I'm positive of. At least the last year or so he is off the grid. But yeah, he couldn't be nicer. And his taste in women is bizarre. At least at one point in his life it was.

I hear a lot of comedians say that they get mistaken for other comedians. Does this happen a lot to you? Wesley Snipes, I get that a lot. A lot of people forget he was a great comic. No, I don't think anyone recognizes me. I don't think I get confused for anybody. Although some people will say, “I really like that joke you did,” and then they recorded a joke my opener did, and I will gladly accept credit for that. I like to bring openers that are a lot better than I am. A lot of comics will bring someone on that's poorer than them so that they look better. But I want people to think, "Hey, who was that first guy. He really has a lot of potential."

I just think it's nice when the audience isn't skipping the opener. I think that's more with bands than with comedy shows.

I guess you're right. And comedians tend to start on time, too. You go to a rap concert and you're lucky if they come on before midnight. I wish I had the balls. I've been to concerts where they start five hours late. I can't even imagine trying to pull that off as a comic. I guess earlier is better for me. I don't want people to be excited or rowdy. I just want them to pay attention and listen, and occasionally laugh. That idea of a pep rally is really the most bizarre reaction that comics go for, that some comics go for. Just the “wooing” and “yeahing” and even coming out to the over the top energy. It's just so ridiculous. It's like “okay, now quiet, listen to my words.” Jokes have never been so funny that I felt the need to scream and cheer. Even among comics that I find gut-wrenchingly hysterical, that has never been my reaction.

You were born in Germany. What's the story there? My parents weren't in the military. There were just having sex and living in Europe at the time. I moved back here when I was three. I grew up mainly down in Florida, which, if you know anything about Florida, it's awful.

It's a place to be avoided. Yeah, I mean, there are different parts of Florida. South Florida, from West Palm Beach to Miami is kind of acceptable, and the rest is just Georgia.

Have you ever been on the radio show Loveline? Yeah, I used to host it—I guest hosted after Adam Carolla had left, like three or four times. I had a good time.

Did they ever play the Germany vs. Florida game where callers read a bizarre story and you have to guess if it came from Germany or Florida? No, but I did Adam Carolla's morning show as the ultimate Germany vs. Florida reporter, and I was the only one that always got it right.

Can you tell us the difference between what's weird about Germany and what's weird about Florida? No, only Adam truly appreciates that. Ninety percent of his questions always go back to that. I assume they're both equally bizarre. Although I find Germany more like Wisconsin than I do any other place in America. It's the weather, I guess. It just seems boring and cold.

What part of LA do you live in? Hermosa Beach

Do you enjoy living near the beach out there? I do, just because it's convenient to the airport, and there is no diversity. No, but it's nice enough, I've live here for about six or seven years, I like the ocean. If you're going to live in Los Angeles, you might as well move all the way west and see the water on a daily basis.

A lot of people end up moving to LA and getting stuck on the East Side, which is fine if that's what they want, but it's not what dreams are built upon. It's kind of like New York, how everyone moves to Brooklyn now. It's like, 'You came here to be near the big buildings, right?' I like that. I think that's how it should be sold, too. "Come for the big buildings."

It's the same with LA, there are certain things that come along with dreaming of living there as a kid and they're not exactly encompassed by living in Silver Lake. No, I completely agree with you. If it wasn't for the Beach Boys' songs, I would have assumed that there was no part of Los Angeles that was acceptable.

Are there any stereotypes of New York that you find hold extremely true? No, except for positive ones. The audiences that come to see me in New York are generally better. And not good as in they like me, I just like an audience where I can say awful, offensive words and they're not mad for the rest of the night. They just let it go, and they like the next joke and I'm back on track. I don't go too far from my comfort zone, which is: venue, restaurant, hotel room. Actually, I take that back, one time I did a show at Caroline's. One time, this guy came up after the show, and I don't have security or anything, I was just standing outside, taking pictures with a couple fans. This guy came up and was really nice, but he was doing that negative nice, saying, “Listen, I need to know, are you really that big of an asshole that you pretend to be on stage?” And at first it was funny, but then it became “I just wanna fucking punch you in the face.” and then it got to the point where it was like, this guy is actually about to hit me, please somebody help me.

Did he tell you what exactly you said that set him off? He never really did. I'm not going to pretend to know what sets people off. And I've watched enough ultimate fighting to know that I don't know which guy I can fight and which one I can't. So I just assume that everyone wants to beat the living shit out of me. But my act overall is insanely condescending and sarcastic, so I'm not going to try to guess what part offended him.