Comedy has never been an art form that rewards beauty or self-confidence. The greatest comic actors — like Woody Allen, Ricky Gervais, Charlie Chaplin, and Will Ferrell — are less than stunning physical specimens who wear their insecurities on their sleeves. And then there are the anomalies, like Paul Rudd. At least on paper, there’s nothing particularly funny about him. With his boyish good looks and charming personality, he seems like somebody who should have the world wrapped around his finger. And yet few actors working today are as believable at portraying what it really feels like to be painfully self-conscious and socially awkward.

Rudd’s movie career has run the gamut of human insecurities. There was the 2005 comedy hit, The 40-Year-Old Virgin, where Rudd played an electronics store employee struggling to forget, or maybe win back, a cheating ex-girlfriend. (“If she wants to be some immature little bitch and blow everybody,” he explained to a co-worker, “that’s love, man.”) In 2007’s Knocked Up, he was a frustrated husband and father acutely aware of the freedoms he’d lost, at one point drunkenly announcing at a dinner party, “Isn’t it weird when you have a kid and all your dreams and hopes go right out the window?” And in the 2009 comedy I Love You, Man, he was a real estate broker clumsily trying to connect with a male friend, inventing cringe-worthy neologisms like “Totes magotes” and “Latress on the menjay.”

Director David Wain, who’s cast Rudd in several of his films over the last decade — from the 2001 cult comedy Wet Hot American Summer to his latest feature, Wanderlust, which opens this month — believes that the dichotomy between Rudd’s pretty-boy exterior and his inner and not-so-easily-concealed insecurity is a large part of the actor’s appeal. “Paul Rudd is a handsome leading man,” Wain admits. “But in his deepest core he’s still the dorky suburban Jewish bar mitzvah DJ he was as a teenager.”

Wain isn’t being hyperbolic. Rudd actually did earn a living during the late 80s and early 90s as a DJ for bar and bat mitzvahs across southern California, sometimes performing under the stage name Donny the Dweeb. But the small town kid from Overland Park, Kansas — he was born in New York City but moved to Kansas at age 10 with his parents; father Michael, a sales manager for TWA Airlines, and mother Gloria — had bigger plans than just hosting parties for Jewish teenagers. One of his first films (after a weird debut in the horror sequel Halloween: The Curse of Michael Myers) was the 1995 teen comedy Clueless, where he played Alicia Silverstone’s Nietzsche-reading stepbrother, a role that the New York Times described as “catnip for sensitive teenyboppers.”

After Clueless, Rudd’s acting work came in essentially two speeds; cute or crude. He was either the non-threatening, mildly quirky boy crush in movies like Object Of My Affection and 200 Cigarettes and TV shows like Friends. Or he was the handsome guy not afraid to make a spectacle of himself in comedies like Anchorman: The Legend of Ron Burgundy and Wet Hot American Summer. But as his résumé grew, it became increasingly apparent that he had more comedic depth and complexity than the roles he was being given. He eventually made the transition to leading man, and his track record has been hit (Role Models and this August’s Our Idiot Brother) and miss (How Do You Know and Dinner for Schmucks). This month he’ll try again with Wanderlust, in which he and Jennifer Aniston star as a New York couple trying to reinvent themselves at a hippie commune in rural Georgia.

Writer Eric Spitznagel, who recently interviewed Jason Sudeikis and Bryan Cranston for Playboy, caught up with Rudd at the Chateau Marmont in Hollywood. He reports: “Rudd and I spent most of an afternoon at the Marmont’s outdoor restaurant, where we consumed four full pots of coffee in rapid succession. Rudd also enjoyed some scrambled eggs with extra bacon, and claimed that the artery-clogging meal was a direct order from director Judd Apatow, who apparently wants Rudd to ‘pack on some pounds’ for an upcoming movie. For a man who jokes as often as Rudd, it can be difficult to tell when he’s just pulling your leg. But he did scarf down an awful lot of bacon.”

PLAYBOY: You seriously have to gain weight for a movie role?

RUDD: I know, it’s weird. It’s the opposite of what the studios normally want, or what other directors want. But it’s different with Judd. He always says, every time we work together, he wants me to gain weight. He’s like, “I like a fat Rudd.”

PLAYBOY: Is that because it makes you look more human?

RUDD: I don’t know, maybe. I just like the excuse to eat bacon. I don’t have far to go anyway. My gut just needs that little extra bit.

PLAYBOY: And this is a typical request from Apatow?

RUDD: Oh absolutely. There’s a line in 40-Year-Old Virgin where my character is telling Steve [Carell] about what it’s like to have your heart broken, and how you’re constantly gaining and losing weight. I improvised that line because before we started shooting the movie, I took Judd’s request to put on weight maybe a little too far. And the studio said, “You’re a fat-ass, lose some weight.” So during the course of the movie, I tried to drop a few pounds.

PLAYBOY: That could cause a continuity problem.

RUDD: A huge problem! And I figured, my weight is going to fluctuate anyway. If I mention it in a scene, maybe that’ll cover my bases and justify why I’m ten pounds heavier in some scenes and ten pounds lighter in others.

PLAYBOY: The new film you’re doing with Apatow is a sequel to Knocked Up?

RUDD: Not really a sequel. It’s more like a spin-off. It’s about Pete and Debbie, the couple that Leslie Mann and I played in the first movie, with the same kids. We’ve been in rehearsals for about six months, reading through scenes and improvising some ideas. That’s actually why I’m out in LA now. We read through some new material the other day.

PLAYBOY: Does it ever feel like you’re doing therapy for Apatow?

RUDD: How do you mean?

PLAYBOY: Your fictional wife is played by Judd’s actual wife, Leslie Mann, and your fictional kids are played by his actual daughters, Iris and Maude. It’s like he’s making these movies to examine his own marriage under a microscope.

RUDD: There’s a reason it seems like he’s doing that. And that’s because he absolutely is. We’re both doing it. It was the same thing in Knocked Up. There’s a lot of stuff in that movie that was right out of my life, and right out of Judd’s life. Judd asked me to write down things from my marriage, and we’d use that in improvisations.

PLAYBOY: Such as?

RUDD: Well, when my wife was pregnant, she got very upset with me because I didn’t read the baby books. She looked at that, understandably so, as a hostile gesture. But I had an argument in my defense. What did the cavemen do without What To Expect When You’re Expecting? You know what I mean? It’s all bullshit. I was like, “It’ll be fine. We don’t need to go to birthing classes or any of that nonsense.” What’s the worst that can happen? It’s not like if I didn’t read the books and go to the classes that our son wouldn’t be born.

PLAYBOY: Is it true you became friends with Apatow because of a mutual love for Steve Martin?

RUDD: Yeah, that’s pretty much what happened. Here’s what happened; I was at a dinner party with a group of people, and we were talking about fake names. You know, how it’s difficult to come up with a really great fake name. It’s a very specific type of gift. You don’t want to go too far into the silly, and you don’t want to go too far into the banal. I always thought one of the funniest names ever was Gern Blanston, which came from a Steve Martin routine on one of his early records.

PLAYBOY: Comedy Is Not Pretty.

RUDD: Yeah, yeah, that’s the one. So I bring up Gern Blanston, and there’s a woman at the table who says, “Oh my god, so that’s what Judd Apatow’s email address means.” Turns out his email address was GernBlanston@aol.com. I thought wow, that’s a very cool, arcane reference.

PLAYBOY: Before you finish that story, a quick side question. Why do so many comics have AOL addresses? Steve Carell has an AOL address, as does Tina Fey and Sarah Silverman. I don’t know about you.

RUDD: I’m AOL.

PLAYBOY: Why is that? Is it a coincidence that almost everybody in comedy is still on AOL?

RUDD: That’s a good question. I never thought about it. I finally got a gmail account but I never use it. I like AOL because it’s so embarrassing. People look at you like you’re a fossil. Which you are. But I enjoy that embarrassment. I like being on the outside. Having an AOL address is like wearing Ocean Pacific shorts. It’s so uncool that it’s cool.

PLAYBOY: Anyway, sorry, you were saying about Apatow.

RUDD: So I have his email address, and I don’t know him but I’m a fan of Freaks and Geeks. When I got home that night from the dinner party, I wrote him a short note, just saying congratulations on the great choice on an email name. And he wrote me back right away, because he was impressed that I knew who Gern Blanston was. And actually, the first thing he said to me was “Cool, now maybe I can get some free tickets to Neil LaBute plays.” Cause at the time, that was the main thing I’d been doing.

PLAYBOY: How long did it take before you met him in person?

RUDD: About a year. We just wrote emails to each other for a long time. I wasn’t actually in the same room with him until I auditioned for Anchorman. And walking in there and seeing him, it was weird. It felt like I was meeting my Asian pen pal. I really wanted to make a great first impression.

PLAYBOY: It probably didn’t help that you’d grown some muttonchops and a mustache.

RUDD: [Laughs.] Yeah, that was pretty great. I wanted to do something special for the role. I was working on Friends that week, so I was able to raid their wardrobe department. I don’t normally dress up for an audition to try and impress the director, unless it’s something that I really, really want and I think it might help. Debra McGuire, who was the wardrobe supervisor on Friends, helped me find this really horrible polyester suit, and I had enough time before the audition to grow a mustache and the chops. It wasn’t fully grown in, but it was enough to give them the general idea.

PLAYBOY: You’ve never been afraid of using your own body for a joke, whether it’s growing a mustache or getting naked.

RUDD: I have been naked in a lot of my movies. I just think there’s something inherently funny about the naked male body, particularly mine. Ryan Reynolds, sure, it makes sense why he’d strip down. But not me. I shouldn’t be allowed to do it.

PLAYBOY: But you keep your clothes on in Wanderlust.

RUDD: Is that surprising?

PLAYBOY: Well, the movie does take place at a hippie commune, and there is male nudity.

RUDD: I was actually pretty thankful that I got to keep my pants on for this one. I’m a big fan of movie nudity. A male ass shot is the cheapest and best laugh ever. But it’s mortifying to do. When I showed my butt in 40-Year-Old Virgin, all I could think about was, “This is going to be up on all those big screens.” I was very self-conscious about doing it. But I also have a desperate and deep-seeded need to be accepted and liked to make up for my massive insecurities.

PLAYBOY: Aside from worrying about the finished product, you don’t mind getting naked for a film crew?

RUDD: I don’t mind it, but I do feel bad for them. There was that scene in My Idiot Brother where I’m naked and getting painted from the side, and because of the angle of the shot, our sound man — who was a guest sound man, by the way, and not even our regular guy — had an unfortunate view. He’s holding up the boom mic and he’s standing right in front of me, and my legs are spread, and he’s pretty much staring at my hairy taint.

PLAYBOY: The poor guy.

RUDD: I felt so bad for him. I could tell by his expression that he was pretty bummed out. Afterwards, I was like, “Sorry about that, man.” I don’t think he forgave me.

PLAYBOY: You mentioned having “massive insecurities.” Are you being coy, or do you actually have insecurities?

RUDD: Are you kidding me? I’m riddled with insecurity. My entire career exists because of insecurity.

PLAYBOY: You honestly believe that?

RUDD: Of course I do. Why would anyone ever be an actor if they’re not insecure? I think that’s why anybody pursues this kind of work. I remember when my sister was born, and I was insecure because I wasn’t getting all the attention anymore. I think you can draw a straight line from that to my entire acting career.

PLAYBOY: Some actors claim they do it for love of the craft.

RUDD: I hear that all the time, and it’s such horseshit. That’s such a lie. There’s nothing I find more revolting than when I’m watching American Idol and some 22-year-old singer thanks the fans and says he’s doing it for them. “I’m doing it for you guys!” Fucking liars. You’re not doing this for your fans. You’re doing this because you want to put food on the table for your family, and you want to be loved by strangers so your self-loathing isn’t as rampant.

PLAYBOY: It can’t all be for the paycheck and the ego stroking, right? You must’ve taken a few jobs because you liked the script.

RUDD: Oh god, yeah, of course. But I’ve been lucky in that way. Very few actors, myself included, are always in a position to say, “Oh, I chose to do this project next.” That kind of luxury is only afforded to maybe a handful of people. I remember what it was like to be thankful for any job, even if it was a shit film.

PLAYBOY: Is that why you did movies like Gen X Cops: 2?

RUDD: Absolutely. What happened there was, I’d made plans to go to London to do a play for about six months. This was right after Wet Hot American Summer, and I was not exactly swimming in cash. I’d definitely passed up on money jobs because I didn’t believe in the content. But at that point I was desperate. So I said to my agent, “I don’t care what it is, just find me a job. I need money fast. I need to pay my rent so I can go to London.” This offer came in, and it was so fucking weird that I couldn’t say no. It was an all-Asian marital arts movie.

PLAYBOY: Had you done anything like that before?

RUDD: Not even close. I’d done comedies and small art films and Shakespeare. Why in the hell would they ever come to me? But that’s why I liked it. I didn’t even need to read the script. I was like, “Fuck yes, I’m in.” I got on a plane that night for Hong Kong.

PLAYBOY: What was your part exactly? You were fighting a robot or something?

RUDD: A killer robot. I was an angry American FBI agent. Everybody else in the movie spoke Cantonese. They bleached my hair blonde and put me in a Hugo Boss suit. When my wife saw it, she said, “You look just like Simon LeBon. If Duran Duran made a music video about the FBI and killer robots, that’s what it would look like.”

PLAYBOY: How did you keep a straight face during the shoot?

RUDD: It was a challenge, but I’d been hired to do a job and I take that seriously. I would never try to mock or make fun of anything I’m doing. But at the same time, I wanted to do it with at least a wink to the audience, but without biting the hand that feeds me.

PLAYBOY: You grew up in Kansas, right?

RUDD: Overland Park, yeah. Since I was ten.

PLAYBOY: Where’d you live before that?

RUDD: All over the place. My dad worked for TWA, so we were constantly moving. We moved to Kansas the first time when I was five, then left when I was six and a half or seven and moved to Anaheim, California. We were in California for three years and then moved back to Kansas. My parents have been there ever since.

PLAYBOY: Did Kansas feel like home?

RUDD: Not at the time. I was Jewish in a not very Jewish part of town, going to a not very Jewish school. My parents were European — my dad and mom were both born in London, and my dad grew up in New York. I always felt a little out of place. I didn’t have a lot in common with the other kids. I’d ask them, “Where are you from?” And they’d say, “Here. What do you mean? I’m from here.” [Laughs.] It was very much a high school football Friday Night Lights scene, which I think it is in a lot of the country. I was not the Friday Night Lights kind of athlete, although I loved football, and I loved the Steelers.

PLAYBOY: The Pittsburgh Steelers? But you lived in Kansas.

RUDD: I started following them when I lived in California. My dad never gave a shit about sports. Once the Dodgers left Brooklyn, he was like, “Fuck sports.” But he worked with a guy who was from Pittsburgh and he loved the Steelers. He took me to game when the Steelers played the Los Angeles Rams, and I got really caught up in the excitement of it. All of a sudden, rooting for the Steelers became my thing. To this day, if I need to remember a number, I’ll associate it with a 70s Steeler player. It’s my mnemonic system.

PLAYBOY: Is that a joke, or have you actually done that?

RUDD: That’s entirely true. On the day I met my wife, I asked her for her phone number, and I’ll never forget this, the last four digits were 1764. I was like, “Oh, that’s easy. Brian Sipe, Steve Furness.” Brian Sipe was a quarterback for the Cleveland Brown, but his number was 17. And Furness, of course, was number 64.

PLAYBOY: In a way, you were letting her know in advance exactly what kind of guy she was getting involved with.

RUDD: Exactly, right. She was like, “What the fuck are you talking about?” The fact that she went out with me anyway says a lot about her. She knew I was a big Steelers fan and a big nerd. In fact, you want to know how much of a Steelers nerd I am? I once made a player entirely out of LEGOs. I made a LEGO version of Craig Colquitt, the Steelers’ punter.

PLAYBOY: Was he your favorite player?

RUDD: No, John Stallworth was my favorite. But Colquitt was number 5, and I only had enough black pieces to do a 5. It was pretty good, if I may say so myself. I made a lot of things out of LEGO when I was a kid, but this was my pièce de résistance. I did it when I was ten, and when I left home after high school, my mom kept it. When people would come over, she’d show it to them. It survived for thirty years. Just a few years ago, I was in Kansas City after my dad passed away, and I found out that the punter for the Kansas City Chiefs, Dustin Colquitt, lives across the street.

PLAYBOY: Any relation to Craig Colquitt?

RUDD: Dustin is Craig’s son! So my mom invites him over, and I bring out the LEGO statue to show him. I was like, “Hey, look what I made when I was ten. I was really into your dad.” I think he was a little freaked out at first, but then he was like, “My dad’s coming to town in a few weeks. He’s got to see this.” I had to fly back to New York, but I was like, “Sure, bring him over, I’d be honored.” But a few days later, my mother was moving some things around, and she accidentally bumped the LEGO Craig Colquitt and it shattered all over the floor. So Craig never got a chance to see it.

PLAYBOY: You must have been devastated.

RUDD: No, I thought it was hilarious. My mother was destroyed. She still feels guilty about it. She’ll probably burst into tears when she reads this. But I had no emotional attachment to it at all. I just enjoyed the irony that it survived for so many years, all those moves around the country, and just when Craig Colquitt was going to come over and see it, crash, it’s all over.

PLAYBOY: Were you the class clown in high school?

RUDD: I wanted to be, but I wasn’t always good at it. I was definitely into telling jokes or trying to make people laugh as a way of dealing with my insecurities. There was once where I was driving in my Jeep with somebody, and I thought it’d be hilarious if I jumped out of the car in the middle of our conversation and then ran next to it, continuing to talk as if nothing was wrong. But it didn’t work out so well. [Laughs.] I ended up slicing open my hands pretty badly. I almost killed myself, and I didn’t even get a laugh. The girl in the car with me was just horrified.

PLAYBOY: When you’re playing a character who’s less than socially graceful, do you ever draw on a painful memory from your youth, a specific time or place when you felt uncomfortable in your own skin?

RUDD: Sure, yeah, I’ve done that.

PLAYBOY: Can you give us an example?

RUDD: Oh god, there were so many. Before you even finished that question, some memory just became unlocked in my brain. I was at a football game, this might have been in junior high or my freshman year of high school. I had the great fortune of puberty hitting me like a max truck, where overnight my hair curled up like Hall and Oats. My skin went bananas and I just had acne all over the place. My mom told me not to pick at my zits, because if I did they’d scar over. So I didn’t touch them, and I was very self-conscious about it. So one night I’m at a party, and there’s this girl that I’ve had a major crush on. She’s part of this social clique that I can’t get anywhere near, I’m so unpopular. I know that people had been making jokes about my zit, so I start joking about it too. I wanted them to think that I didn’t care, that this huge mega-zit on my face was no big deal to me. And this other girl, one of the leaders of the clique, she says, “Oh, Paul is just looking for attention, like he always does.” She just belittled me in front of everybody, including the girl that I liked.

PLAYBOY: Did you say anything in your defense?

RUDD: Not at all. I just laughed. But inside, of course, I was distraught. I went into the bathroom and looked in the mirror and I was like, “Fuck it!” I just squooshed the zit, and puss squirted everywhere. The way I felt in that moment, it’s the same feeling I’ve had in varying degrees throughout my entire life. It’s helplessness and shame and anger.

PLAYBOY: It doesn’t go away.

RUDD: It doesn’t. And I think in some cases, I’m really glad it doesn’t go away. Because, well, at least for me, I’ve learned to capitalize on that feeling. I’ve devoted my entire acting career to reproducing and dwelling on that feeling. Every character I’ve played is just a variation on that kid with a zit he’s terrified of popping.

PLAYBOY: Did you feel like that awkward kid when you visited President Obama at the White House a few years ago?

RUDD: Oh man, completely. I sweat through a sport coat, which I’m pretty sure is the first time I’ve ever done that. Because nothing about that was planned. I was in Washington D.C. to shoot How Do You Know, and Reese [Witherspoon] and I were taking a tour of the White House. All of a sudden, we were taken into some room, and then a door opened and there was Obama. I’d never seen Reese get flustered, but when he asked her who else was in the movie, she was like, “Jack Nicholson and me and Owen… Owen… Owen…” And I shouted, ‘Wilson!’ Like it was a party game or something. She forgot his name for a second. And then he made a joke to me, which I completely missed.

PLAYBOY: What was the joke?

RUDD: He asked about my character in How Do You Know, and I told him that I’m a guy who gets into some hot water and although his intentions are good he gets indicted by the government for possible violations. And Obama says, “Oh, so you’re playing a Congressman.” And I was like, “No, actually I work for my dad in this corporation.” I’m trying to explain, and Obama interrupts me and says, “It was a joke.” I just felt so stupid. Of course it was a joke, and it’s actually a pretty good one. I’m normally pretty good at catching that. If you’re not the fucking president of the United States, I can usually identify when somebody’s joking.

PLAYBOY: You didn’t set out to be a comic actor, right? Your original goal was to be a Shakespearian actor.

RUDD: That was the plan. Maybe not exclusively Shakespeare, but definitely serious theater. I was pretty focused. One of my first acting roles in college was an experimental version of MacBeth.

PLAYBOY: Experimental how?

RUDD: There were two MacBeths. Some other guy played the bad MacBeth and I…[Laughs.] I played the good MacBeth.

PLAYBOY: That seems unnecessarily confusing.

RUDD: Oh, confusing was the least of it. It was incredibly stupid and pretentious and awful and I loved it. The director was one of those guys who didn’t wear shoes, and he wanted to do something fascinating and explosive. At the time, it seemed so cool to me. I was 18, maybe 19, at that age where everything seemed incredible. “Holy shit, you’re telling me you can set Hamlet in Vietnam?” It’s that moment in your life when you realize the world is so much bigger than you imagined.

PLAYBOY: Was it around this time that you started working as a DJ?

RUDD: Yeah, I think so. I only did it occasionally, at this place called Studebakers, which was a 50s themed bar in Kansas City. I had long hair like Michael Hutchence, the guy from INXS, and I refused to cut it. So my bosses made me wear an Elvis pompadour wig every time I worked. It was jet black and cheap and over time it got frizzy and didn’t look like a pompadour at all. When I moved to Los Angeles, one of the guys who also DJed at Studebakers was working for a company called You Should Be Dancing, and he got me a job. I spent my weekends doing bar mitzvahs and keeping 16-year-olds psyched about MC Hammer.

PLAYBOY: You became famous on the bar mitzvah circuit for something called the Donny the Dweeb dance?

RUDD: Oh Jesus. That happened after an oppressively long day. I had two bar mitzvahs in one day, the first in Santa Barbara and the other in Thousand Oaks. With all the traveling involved, it was like an 18 hour day. Somewhere around the middle of the second bar mitzvah, I was on the dance floor with these kids and I guess I just cracked. I couldn’t take it anymore, and I got so slap-happy that I started dancing spastically, kind of mocking the whole thing just to entertain myself. But I guess the kids thought it was funny, and the following week I was at another bar mitzvah and some kids came up to me and said, “Hey, you’re the guy who does the dork dance. “And I was like, “I don’t know what you’re talking about.” And they’re like, “Last week at so-and-so’s bar mitzvah, you did this dance.” They went to my boss and begged him to make me do it. And my boss was like, “Look man, you have to do it.” So I went out there and he got on the microphone and said, “Ladies and gentlemen, please welcome Donny the Dweeb!” He gave me a name.

PLAYBOY: What exactly happened during this dance?

RUDD: I don’t know how to describe it without offending many groups of people. It was a combination of…. let’s just say some mental disabilities and physical ailments. The full front of negative stereotypes. With socks pulled up. It’s pretty much a metaphor for how I felt about the zit in high school. I was putting on a show for everyone, while inside I felt like Coco in Fame, taking off my shirt and showing my breasts for a casting director. That’s how I felt about it. It became kind of a recurring theme for me.

PLAYBOY: Is it that same dorky dance you’ve done in movies like 40-Year-Old Virgin?

RUDD: No, it’s a little different. But it’s the same level of shame. In much the same way I can’t think about the Donny the Dweeb dance, I can’t watch that closing sequence in 40-Year-Old Virgin without getting a little sick to my stomach.

PLAYBOY: Why?

RUDD: Because it’s horrible and sad and gross. I don’t want to look at that. In the moment, while we were shooting that scene, I embraced it whole hog. But I don’t want to see it on the screen. If I’ve learned anything from my acting career, it’s that you’ve got to throw yourself in front of the truck. If you don’t like what you’re doing or it’s horrifying and scary and you know it’s going to be personally humiliating, you just do it anyway. It’s that same mentality that made me jump out of a Jeep to get the laugh. I knew at the time that it was really, really stupid. But if there was a chance it’d make people laugh, I had no problem with a little physical danger.

PLAYBOY: Why’d you give up being a bar mitzvah DJ? Did it only happen when your acting career finally took off?

RUDD: Oh no, it was long before that. I had some friends coming to town. We were going out to the Magic Castle. So I told my boss a month in advance, “I need Saturday night off.” But then the weekend comes, and I ended up getting requested for this girl’s party. She really wanted Donny Dweeb. So my boss says to me, “Can you just stop by and do the dance? I’ll give you $25 and you can get out of there.

PLAYBOY: Did you do it?

RUDD: I did. And I brought along my friends. One of them was Joe Buck, who went on to become a play-by-play announcer for Fox Sports. And the other guy was Jon Hamm.

PLAYBOY: From Mad Men?

RUDD: Yeah. Both these guys I’ve known since I was a teenager. They come into town, and I’m like, “Before we go to the Magic Castle, we need to swing by to this party. I just have to do this one quick thing.” So we go, and they have no idea what I’m doing. They knew that I was DJ for parties, but they had no clue how bad it’d gotten. My boss sees my friends and he says, “I’ll introduce Paul, and you guys can come in as his henchmen.” I guess because they were wearing suits.

PLAYBOY: Wait, hold on. You and Jon Hamm and Joe Buck are all in suits?

RUDD: We had to be, because there’s a dress code at the Magic Castle. So Jon and Joe come out and they’re standing to the side, and I pull the bat mitzvah girl from the audience and put her in a chair in the center of an empty dance floor. And in front of hundreds of guests and family members, I essentially give this teenage girl a retarded lap dance.

PLAYBOY: Wow. That sounds….

RUDD: Disturbing?

PLAYBOY: That’s one word to describe it.

RUDD: It’s the only word! But at this point, I’d become numb to it. After it was all over, I walk over to my friends and I’m like, “Okay guys, let’s go.” Very casual. We go out to the lobby, and I’ll never forget this, Joe Buck looks at me with the most confused expression on his face. And he says, with utter earnestness and sincerity, “What the fuck just happened in there?” And at that moment, the reality of what I’d been doing with my life came crashing down. I answered him the only way I could. I said, “I honestly don’t know.” The next day, I gave my notice. I quit. I never DJed again.

PLAYBOY: Even without the DJ job, you weren’t particularly happy in Los Angeles.

RUDD: I wasn’t.

PLAYBOY: You once claimed that you had a “meltdown” during the mid-90s. What happened exactly?

RUDD: It was a series of things coming down on me all at once. I got a job on this TV show called Wild Oats, and it made me skittish. I kept asking myself, “What if it’s a hit? I’ll have to keep doing it for seven years.” The audition was fun, because we got to improvise and goof around, and it felt like it could be okay. But I got cold feet. My hand was literally shaking as I signed the contract. Even though I needed the money and I was lucky to be a working actor, I was 24 and precious. This is where acting and youth really screws with you. I wanted to do theater, I wanted to do cool indie movies.

PLAYBOY: It got so frustrating that you painted obscenities on the walls of your apartment?

RUDD: Yeah, but that was just a product of age. It seems so romantic to paint on your walls and feel like a tortured artist when really you’re just a whiner. I’d write things like, “Fuck this, fuck that,” I wrote about all the things that were getting to me. This was around the time of that Northridge earthquake, in 1994 I think, which was very traumatic for me. It happened in the middle of the night, and it spooked me so much that for the next few months I was constantly feeling earthquakes. I’d be in the middle of a conversation with somebody and I’d say, “Did you feel that?” And they’d be, “No. What are you talking about?” It was a weird thing. I just didn’t feel sure footed anymore. There were a bunch of traumas that happened to me in a short amount of time. A friend of mine was killed in an awful car accident. And then I got mugged. It was right around the time we were shooting Clueless. I was in the parking lot of Jerry’s Deli, and the guy was like, “You don’t think it’s a real gun?” And he shot it at me, and I could feel the breeze from the bullet next to my head.

PLAYBOY: Did it seem like Los Angeles was telling you to get out?

RUDD: Wait, wait, it gets better. I got into five car accidents in just one week.

PLAYBOY: Five car accidents? How is that possible?

RUDD: Two of them happened when my car was parked. I wasn’t even driving at the time. It really did seem like a weird cosmic message from the universe. I’m not somebody who lives my life based on cosmic anything, but it really did feel like, “Oh yeah, I get it. Message received, universe.”

PLAYBOY: Why move to New York?

RUDD: Because in New York, you don’t need a car. [Laughs.]

PLAYBOY: That can’t be the only reason.

RUDD: I lived there as a kid. I was born just across the bridge. So it was very familiar to me. And I’ve always felt safer in New York than I did in Los Angeles, as weird as that sounds. I don’t want to be surrounded by the industry all the time, and that’s what you get in Los Angeles. I remember not long after I moved to New York, I was cast in this play called Last Night of Ballyhoo, and I was walking to rehearsal, holding my script and some coffee, and I just felt so… sane.

PLAYBOY: You didn’t usually feel sane?

RUDD: Not really, no. [Laughs.] It’s easy to feel insane in Los Angeles. But here, doing this play, I felt part of something so much bigger than anything I’d done before. Which was weird, because Clueless had come out and become this huge hit and everybody had seen it. By comparison, at least according to my agents, the play was a step backwards. Maybe it was a mistake, at least in terms of career opportunities. But every day, I just felt lucky and happy and sane.

PLAYBOY: Did you drag a wife or girlfriend to New York?

RUDD: No, I wasn’t dating at the time. In fact, one of the first people I met in New York was Julie, who became my wife.

PLAYBOY: That’s kind of eerie.

RUDD: It is, isn’t it? She worked for a PR firm, and when I got to New York that’s the first place I went. I didn’t know anybody in New York, and we went out to coffee and got to know each other. We connected on a very intense and deep level about some very serious things. We’d both just gone through some incredibly traumatic and transitional moments in our lives. She told me that she’d been engaged and her fiancee had died, and that’s how she decided to get involved in publicity, because she needed something to do just to fill her days. And that was our connection, talking about death. [Laughs.] That’s New York to a tee. I ended up staying at her apartment, just while I looked for a job and a place to live. We eventually got an apartment together, and we’ve never not lived together since. It’s going on sixteen years now.

PLAYBOY: But you’ve only been married for half of that?

RUDD: We were together for eight years before we got married.

PLAYBOY: Why’d you wait?

RUDD: I don’t know. Nervousness maybe? I was like, “Why rock the boat?” We just didn’t really talk about it. And then it became more about age and having kids. Everything changes when you become parents. You’re not as worried about clinging to your independence.

PLAYBOY: You have a son, right?

RUDD: That’s right. Jack. And a daughter. She’s one and a half.

PLAYBOY: I assume they haven’t seen your movies.

RUDD: Oh god no. Not yet. But honestly, they’re just not curious. Jack, who’s six now, doesn’t have any interest. I think because of home videos and YouTube, it just doesn’t seem that special. He hasn’t figured out the distinction between seeing himself in a video and what I do. He’s starting to now. Before, if somebody approached me on the street, it would be confusing to him. He’d be like, “Do you know that person?” And I’d tell him no, and he’d say, “Well how do they know your name?” Now he gets it. He’s like, “Oh, they know you from the movies.”

PLAYBOY: What about Sesame Street? You did a few skits for the show not long ago. He must’ve seen those.

RUDD: Nope. He wanted nothing to do with it. Didn’t watch it, and still hasn’t seen it. I did that when he was three, and that was when he was really into LiveAid. He didn’t care about kids’ shows, he just wanted to watch LiveAid. The one from 1985. He didn’t watch Sesame Street at all.

PLAYBOY: He’s into rock music?

RUDD: He’s a musical fanatic. Always has been. And he’s a very good drummer, kind of prodigy good. I have video of him at two or three years old that would get millions of hits on YouTube. So when I was shooting Sesame Street, I brought him with me, and they’re so great to kids on that show. One of the things they did was make a little video of Jack at Sesame Street with Elmo and Abby Cadabby. They tried to sing with him but he just wanted to stare at himself in the monitor. And then they tried hugging him, and he was like, “This is exactly like that Bruce Springsteen video for Rosalita.”

PLAYBOY: Your movies are not exactly family friendly. There’s lots of cursing and sexual scenarios. When your kids are old enough to watch what their dad does for a living, will you be tolerant when they start dropping the f-bomb?

RUDD: I don’t know. I definitely make a concerted effort not to use profanity when I’m around them, but sometimes I do. And when it happens, I just tell them not to do it, too. I think my job as a parent is to confuse my kids as much as possible. [Laughs.] It’s hard though. When Jack swears, I’ll laugh every time. And I know it’s the wrong reaction to have.

PLAYBOY: It’s certainly not going to discourage him.

RUDD: I know, I know. It blurs the line between father and son. I’ve had many moments when I’m laughing with him at the most puerile stuff. Yesterday, I was picking him up and then throwing him onto his bed, and he kept kicking me in the nuts. One time he hit me so hard that I said, “Dude, you just totally nailed me in the penis. Right on the tip.” He laughed and he was like, “In the triangle?” And I started laughing and said, “Yeah, that’s it.” And then he was like, “Right in the roof of the house?” I just died.

PLAYBOY: So your son’s become a guy friend?

RUDD: That’s it exactly! He’s a dude that I want to hang out with. There’s no parenting book I can refer to when my kid just starts making hilarious jokes about the tip of a dick being the roof of the house. All I can do is laugh and give him a high-five and say, “Nice one.” My son’s always been bizarre and funny. For like a year he was obsessed with sprinkler heads. And between the ages of 3 and 5, he would only dress in a suit. He wouldn’t leave the hours without wearing a coat and tie and dress pants. I remember thinking, “This is my dream kid.”

PLAYBOY: How did Jack come to have an Irish pub named after him?

RUDD: You heard about that? [Laughs.] He actually has two. The first one was built by his grandfather. Around the time Jack was born, my parents moved into a new house in suburban Kansas City. And my father was a very handy man. He could build homes, he could do anything. He had this unfinished basement, and he was like, “I’m going to build an Irish down there, and I’m going to call it Sullivan’s.” Which is Jack’s middle name.

PLAYBOY: Is that a family name?

RUDD: Not at all. Nobody in my family is Irish. But my father was a huge lover of Ireland. He used to travel over there all the time. Thus the Irish pub. He had all these rules about it. It was going to have Guinness and good beers and no Coors Lite. There’d be single malts and high-end whiskeys and nothing with an umbrella in it. On the shelf behind the bar, he’d have Jameson and Glenlivet and [the baby formula] Similac. He always said, “Jack is the proprietor. He’s the owner.” The only thing he asked of me was a picture of Jack that he could have sepia toned and made to look like an old photograph to put above the bar.

PLAYBOY: Did you help him build it?

RUDD: No, it was a complete secret. He never sent me pictures, never gave me updates. I just knew that he was working on it, putting in plumbing and electricity and everything. And after a year, he said, “It’s done. Come back to Kansas and bring Jack. I want you to see it.”

PLAYBOY: Was it as amazing as you imagined?

RUDD: It was better. My dad was really good at building stuff, but this was his masterpiece. I went down to the basement and… I don’t even know how to describe it. It’s like there was an old Irish pub already there that somebody had built a home on top of. He had Guinness on draft and incredible historical paraphernalia on the walls. My dad was a history fanatic and collected all sorts of weird things. There was a framed invitation to FAO Schwartz to attend the grand opening of the Brooklyn Bridge. An old New York City police uniform from the late 1800s. An Olympic ‘36 document signed by Hitler. Being Jews, we’re all obsessed with Hitler. No Irish pub is complete without having some Nazi paraphernalia on the walls.

PLAYBOY: When did the second pub happen?

RUDD: Well, I told my dad that if I ever bought a house, now that I’d seen what he’d done, I’d need to have a pub in it. So when Julia and I decided to buy a place in upstate New York, the first thing I looked for was whether it had a basement with enough room to build a pub. We found one in Rhinebeck, and right away I started working on my own basement pub. My father was going to come out and we were going to do it together, but then he got diagnosed with cancer. Over the course of a year, I hired somebody and built another version of Sullivan’s, which I called Sullivan’s East.

PLAYBOY: How does it compare with the original?

RUDD: I must say, I improved on it. It’s a little bigger, and I learned a lot of things from my father. He told me, “If I had it to do over again, I’d make sure to do this and this.” The only thing I feel was a lost opportunity, I didn’t put in a urinal. But it’s still got some great things that I’m really proud of. There are markers in the bathroom so people can write horrible things all over the walls.

PLAYBOY: Did your dad live long enough to see it?

RUDD: [Long pause.] He didn’t, no. [Another long pause.] It’s funny, Sullivan’s, the original Sullivan’s, was a tribute to my son, and Sullivan’s East has become a shrine to my father. My sister had a son and his full name is Henry Sullivan Arnold. She gave him the middle name Sullivan so that he could be a co-owner of the pub. [Laughs.] Because she and her husband didn’t want Henry to grow up not feeling a part of the family business.

PLAYBOY: Have your friends and co-workers seen the pub?

RUDD: Oh yeah, everybody’s been there, everybody I’ve worked with. There’ve been a few live fantasy football drafts, a few poker weekends, a few karaoke parties.

PLAYBOY: Karaoke is especially popular among comics, isn’t it?

RUDD: Wildly popular. [Wanderlust director] David Wain, he’s a big fan of karaoke. As is Joe Truglio, Ken Marino, all of those guys from Wet Hot American Summer.

PLAYBOY: Why is that? Is it like AOL email addresses? It’s so uncool that it’s cool?

RUDD: [Laughs.] That may be part of it. When comics get together to do karaoke, it’s not like anybody is trying to be funny. But at the same time, nobody is taking it too seriously. It’s hard to explain.

PLAYBOY: Do you have a favorite karaoke song?

RUDD: Not at all. That’s a rookie move. I had a karaoke song like ten years ago. Now I like to do ones I’ve never done before.

PLAYBOY: So what do you look for in a karaoke song? Does it need to be in your vocal range, or something more challenging?

RUDD: A lot of these decisions are made based on who I’m ‘raoking with. And please spell ‘raoking correctly, without the k and a and with an apostrophe. Everybody I know, they all refer to it as ‘raoking. And yes, I do realize how pathetic that sounds.

PLAYBOY: Don’t apologize.

RUDD: Oh, I’m not. Not at all. That’s just the way it is. If I’m in Los Angeles for a day or two, I’ll call Joe Trigly, and we’ll go ‘raoking. That’s just my social scene now. A few weeks ago, I was out in LA and Joe and his girlfriend Beth and I got a private room. Joe and I, we like to give each other some surprises. You got to go deep in the book and find something that the other person hasn’t heard.

PLAYBOY: Like what?

RUDD: The last time I went ‘raoking, Joe did “The Worst That Could Happen” by Johnny Maestro & The Brooklyn Bridge. It’s an impossible song to sing, but it’s incredible. It’s kind of unintentionally sexist but it’s just incredible. When you find a song like that, it’s like hitting hitting oil. The first question we always ask before going to a new ‘raoking place is “How’s the book?” We don’t want a standard book. [Laughs.] You want to talk about socially awkward? Come to a ‘raoking session with a bunch of comics. That’s where you’re gonna see the magic happen.

(This story originally appeared, in a slightly different form, in the October 2011 issue of Playboy.)