A wild-mannered legend of comedy history, Jon Lovitz has created a mid-tempo career with roles on The Simpsons and in movies like Casino Jack and Woody Allen's Small Time Crooks since his unforgettable years as a pathological liar and Jewish Santa on Saturday Night Live. Rarely a leading man and at times embroiling himself in controversial feuds (such as his bust-up with Kevin Smith last summer, when Lovitz spewed a divisive rant against Obama), this character actor has delivered some of the most beloved jerks in comedy cinema.

Starting tonight, Lovitz will perform four shows of standup comedy at Comedy Works South. In anticipation of these shows, we touched base with Lovitz to chat about playing the villain, why The Critic was cancelled, and what he really thinks of Barack Obama.

See also: Mike Birbiglia on funny sadness and self-deprecating comedy

Westword: Straight off, I want to say that I was a huge fan of The Critic in the early '90s. I really wish it had been given more of a chance. Do you think it was cancelled because audiences couldn't sympathize with a film critic? Jon Lovitz: Thanks. The thing is, the show was actually making fun of critics, and at the time the show was a hit with audiences. But for whatever reason, the network didn't like it. Jim Brooks was like, "They're canceling a hit, what are they doing?" Al Jean and Mike Reiss didn't have a clue. It was disappointing. It held 90 percent of The Simpsons audience at the time, which was at its peak.

I really loved that Simpsons crossover episode. When Jay Sherman and Homer Simpson's bellies were growling at each other under the table, I don't know when I've laughed so hard.

Oh, thank you. Yeah, Al Jean and Mike Reiss wrote the part for me, so I got lucky there. Al's still running The Simpsons.

You had a whole host of Simpsons characters you played: Artie Ziff, the Llewellyn Sinclair crazy theater director, Ms. Sinclair. Similar to your film roles, you seem to be attracted to arrogant, emotionally broken characters. What is the appeal for you in playing villainous characters?

With someone like Artie Ziff, it was kind of an arrogant idiot who was unaware of it. There's something about that that's inherently funny to me. I don't know if I'd say Artie Ziff was a villain; he's just someone who's still in love with his girlfriend from high school. I would say that most of my characters are likable jerks. But I never saw them as villains. They're usually pretty harmless.

With the pathological liar character...you know, I hate lying. So I created that character based on that. I think lying is deplorable, and I wanted to make fun of that. I really like old movies, and there was a character in The Thin Man that would say, "Yeah, that's the ticket." And I thought, "Oh, that would be a fun part to play." And then I thought of AA -- which isn't very funny -- but I thought what if a guy did like an AA kind of stand- up, tell your story, but said he was a pathological liar, and when he told his story he was just lying. But he thinks he's getting away with it. That made me laugh. I wanted to make him likable; he's a good person, but he has this flaw.

I've been curious to ask someone who's appeared on the Comedy Central roasts about the overwhelming amount of "You're gay!" jokes that run on the show. I know you had a song about Bob Saget along those lines, and the recent James Franco roast was almost nothing but jokes like that. It's not that they're offensive, it's just that it doesn't seem like an insult to be thought of as gay in the 21st century.

Well, it's not really making fun of gay people; the joke is just about saying someone isn't very masculine, or something. It's immature. It's like eight-year-old humor. It's silly. It's where you're coming from that matters. I have a lot of gay friends, and I tease them and they tease me. It's not coming from a mean place. When the roast jokes are silly and over the top, they're funny, but sometimes they're just mean. And I don't like to do those kinds of jokes. But sometimes people get too politically correct, which is kind of the antithesis of comedy.

Yeah, and if you look at the context of that, it was me talking in my own comedy club in front of a comedy audience. I just said it to get a laugh, do you know what I mean? That's what I sell.

I was complimenting him by saying he'd achieved so much in his life, but then also that he's being hypocritical. Some people claimed I was racist, but I said they were the ones being racist. Because they look at the president as a black man or a white man, but I look at him as a man. He's the president. I mean, I voted for him. I was making fun of George Bush for eight years and no one complained.

Exactly. It seems like for a lot of comedy fans, when it comes to politics, they're desperate to categorize you into left or right. You're either on the left with Jon Stewart and Bill Maher, or you're on the right with Dennis Miller and Adam Carolla. There doesn't seem to be room for any nuanced opinions.

Yeah, you know Bill Maher does his political show, and he's clearly for Obama. And I don't care about that. It's when they take a comedian and give them the weight of the government, like they're in the White House cabinet or something. And the whole point of a comedian or an actor is just to look at life in the mirror and say, "Here's what I see." It's just a personal opinion.

When that video of me went viral, I was just like, what's the big deal? Who cares what I think about politics? With Obama, I supported him, and then he's saying that people aren't paying their fair share of taxes; he was creating a false class system in the United States to get votes. It's just a typical political ploy when there's a bad economy, you find a scapegoat. Hitler did it with the Jews and Obama did it with the 1 percent. I'm not saying Obama is Hitler, I'm saying it's a political ploy. You tell people that it's not them, it's this minority, they're the ones messing everything up. The whole idea of 99 percent vs. the 1 percent is a bunch of crap, anyway. These comments lead to a rift between you and Kevin Smith, right? I know you two had a business deal that also went sour around that same time.

I'll just say that they did their whole thing, and told a bunch of lies. They were trying to gouge me. Most of the stuff they said wasn't true. Ask any club owner in America, and see what they'd say if someone asked for 100 percent of the door and control of all the ticketing services. Kevin Smith has never owned a club.

Look at Kevin Smith: he's always in a fight with somebody. And I was not fighting with him. It was manufactured horseshit. He made me an offer that anyone would refuse, and then he got mad about it. It's ridiculous!

There's something that's been on my mind today that I'd like to get your take on, which is the designation of "clean comedy." There's a show called The Clean Guys of Comedy that's coming to town this week, and it got me thinking about how that side of the industry is made up of people who aren't buying a ticket for any specific performer or theme of the show -- it's the absence of very specific moral speedbumps. In your career, have you had to deal with many shows like this? I don't think my show would fit into a clean comedy show; but I don't think there's anything wrong with those shows. To me the issue isn't whether you're working dirty or clean, but are you funny? Clean is just another way of saying the show is rated G: There's no cursing, no sex jokes, that's all.

Who are the comics in this show?

Dave Coulier, Jamie Kennedy and a few others.

Jamie's on it? Well, I know both those guys, and they're very funny. When people come to my show, I tell them it's rated R. I like being able to say whatever I want in standup, as opposed to TV where there's a network and all that. But that's just my choice. When I first started writing jokes for a living, it was for the Friars Club in New York, before Comedy Central. And the whole point of those roasts was they were a private function. In other venues you had to work clean, but at these roasts it was private, and so you wanted to be as dirty as you could be. Jon Lovitz will perform four shows on Friday, September 20 and Saturday, September 21 at Comedy Works South, 5345 Landmark Place in Greenwood Village. Tickets are $32. For more information, visit www.comedyworks.com. For more comedy commentary, follow me on Twitter at @JosiahMHesse.

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