Comedy has never been an art form that rewards beauty or self-confidence. The greatest comic actors—such as 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. 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 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, in which Rudd played an electronics store employee struggling to forget, or maybe win back, a cheating ex-girlfriend. In 2007’s Knocked Up he was a frustrated husband and father acutely aware of the freedoms he’d lost, at one point announcing at a restaurant, “Isn’t it weird, though, 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 agent clumsily trying to connect with a male friend.

Director David Wain, who has cast Rudd in several of his films over the past decade—from the 2001 cult comedy Wet Hot American Summer to his next feature, Wanderlust —believes the dichotomy between Rudd’s pretty-boy exterior and his 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 in the early 1990s as an MC and DJ for bar and bat mitzvahs across southern California, sometimes performing under the stage name Donnie the Dweeb. But the suburban kid from Overland Park, Kansas—he was born in Passaic, New Jersey but moved to Kansas at the age of 10 with his father, Michael, a sales manager for TWA, and mother, Gloria—had bigger plans than just hosting parties for Jewish teenagers. One of his first films was the 1995 comedy Clueless.

After Clueless, Rudd’s acting work came in essentially two speeds: cute or crude. He was either the nonthreatening, mildly quirky boy crush in movies like The Object of My Affection and 200 Cigarettes and on 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. He eventually made the transition to leading man, and his track record has been hit (Role Models and I Love You, Man) and miss (How Do You Know and Dinner for Schmucks). Soon 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.

Eric Spitznagel, who has interviewed Tina Fey and Steve Carell for ­Playboy, caught up with Rudd at the Chateau Marmont in West 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.”

You seriously have to gain weight for a movie role?
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, that he wants me to gain weight. He says, “I like a fat Rudd.”

Is that because it makes you look more human?
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.

And this is a typical request from Apatow?
Oh absolutely. There’s a line in The 40-Year-Old Virgin when my character tells Steve Carell 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.

That could cause a continuity problem.
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 10 pounds heavier in some scenes and 10 pounds lighter in others.

Is the new film you’re doing with Apatow, currently called This Is Forty, a sequel to Knocked Up?
It’s not really a sequel. It’s more like a spin-off. It’s about Pete and Debbie, the couple Leslie Mann and I play in the first movie, with the same kids. We’ve been in rehearsals for about six months, reading through scenes and improvising some ideas.

Does it ever feel as though you’re doing therapy for Apatow?
How do you mean?

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 as though he’s making these movies to examine his own marriage under a microscope.
There’s a reason it seems as though he’s doing that. And that’s because he absolutely is. We’re both doing it. It was the same thing in Knocked Up. A lot of stuff in that movie 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.

Such as?
Well, when my wife was pregnant, she got upset with me because I didn’t read the baby books. She looked at that, understandably, 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 as though if I didn’t read the books and go to the classes our son wouldn’t have been born.

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

Comedy Is Not Pretty!
Yeah, that’s the one. So I brought up Gern Blanston, and a woman at the table said, “Oh my God, that’s what Judd Apatow’s e-mail address means.” It turned out his address was I thought, Wow, that’s a very cool, arcane reference.

Before you finish that story, a quick side question: Why do so many comics have AOL addresses? Steve Carell has an AOL address, as do Tina Fey and Sarah Silverman. What about you?
I’m AOL.

Why is that? Is it a coincidence that almost everybody in comedy is still on AOL?
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 as if 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.

Anyway, sorry—you were saying about Apatow?
So I have his e-mail address, and I don’t know him, but I’m a fan of Freaks and Geeks. When I got home from the dinner party that night, I wrote him a short note congratulating him on a great choice in e-mail names. And he wrote back right away because he was impressed I knew who Gern Blanston was. Actually, the first thing he said to me was “Cool, now maybe I can get some free tickets to Neil LaBute plays.” Because at the time that was the main thing I’d been doing.

How long did it take before you met him in person?
About a year. We e-mailed 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 was weird. It felt as though I was meeting my Asian pen pal. I really wanted to make a great first impression.

It probably didn’t help that you’d grown some muttonchops and a mustache.
[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 the show’s wardrobe department. I don’t normally dress up for an audition to try to impress the director unless it’s something I really want and I think dressing up might help. The wardrobe supervisor on Friends helped me find this 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.

You’ve never been afraid to use your own body for a joke, whether it’s growing a mustache or getting naked.
I have been naked in a lot of my movies. 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.

But you keep your clothes on in Wanderlust.
Is that surprising?

Well, the movie does take place at a hippie commune, and there is male nudity.
I was actually pretty thankful 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 The 40-Year-Old Virgin, all I could think 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-seated need to be accepted and liked to make up for my massive insecurities.

Aside from worrying about the finished product, you don’t mind getting naked for a film crew?
I don’t mind it, but I do feel bad for them. There’s that scene in Our Idiot Brother where I’m naked and getting painted from the side, and because of the angle of the shot, our soundman—who was a guest soundman, by the way, and not even our regular guy—had an unfortunate view. He was holding up the boom mike and standing right in front of me. My legs were spread, and he was pretty much staring at my hairy taint.

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

You mentioned having massive insecurities. Are you being coy, or do you actually have insecurities?
Are you kidding me? I’m riddled with insecurity. My entire career exists because of insecurity.

You honestly believe that?
Of course I do. Why would anyone be an actor if he or she weren’t insecure? 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.

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

You seem very neurotic for someone who grew up in Kansas.
I’ve lived 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. We were in California for three years and then moved back to Kansas. My parents have been there ever since.

Did Kansas feel like home?
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, though I loved football, and I loved the Steelers.

The Pittsburgh Steelers? But you lived in Kansas.
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 a game when the Steelers played the Los Angeles Rams, and I got 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 1970s Steelers player. It’s my mnemonic system.

Is that a joke, or have you actually done that?
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 Browns, but his number was 17. And Furness, of course, was number 64.

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

Was he your favorite player?
No, John Stallworth was my favorite. But Colquitt was number five, and I had only enough black pieces to do a five. It was pretty good, if I may say so myself. I made a lot of things out of Legos when I was a kid, but this was my pièce de résistance. I did it when I was 10, 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 30 years. Just a few years ago I was in Kansas City after my dad passed away, and I found out the punter for the Kansas City Chiefs, Dustin Colquitt, lives across the street.

Any relation to Craig Colquitt?
Dustin is Craig’s son. So my mom invited him over, and I brought out the Lego statue to show him. I was like, “Hey, look what I made when I was 10. 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 accidentally bumped the Lego Craig Colquitt, and it shattered all over the floor. So Craig never got a chance to see it.

You must have been devastated. 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.

Were you the class clown in high school?
I wanted to be, but I wasn’t always good at it. I was definitely into telling jokes and trying to make people laugh as a way of dealing with my insecurities. Once 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 my hands open pretty badly. I almost killed myself, and I didn’t even get a laugh. The girl in the car with me was just horrified.

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?
Sure, yeah, I’ve done that.

Can you give us an example?
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 may have been in junior high or my freshman year of high school. I had the great fortune of having puberty hit me like a Mack truck, where overnight my hair curled up like Hall and Oates’s. My skin went bananas and I 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. One night I was at a party, and there was this girl I had a major crush on. She was part of a social clique I couldn’t get anywhere near because I was so unpopular. I knew people had been making jokes about my zit, so I started joking about it too. I wanted them to think I didn’t care, that this huge megazit on my face was no big deal to me. And this other girl, one of the leaders of the clique, said, “Oh, Paul is just looking for attention, like he always does.” She just belittled me in front of everybody, including the girl I liked.

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

Does it go away?
It doesn’t. And in some cases I’m really glad it doesn’t go away, because, 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 of that kid with a zit he’s terrified of popping.

Did you feel like that awkward kid when you visited President Obama at the White House a few years ago?
Oh man, completely. I sweated through a sports coat, which I’m pretty sure is the first time I’ve ever done that. 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.

What was the joke?
He asked about my character in How Do You Know, and I told him I’m a guy who gets into some hot water, and though 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 them. If you’re not the fucking president of the United States, I can usually identify when you’re joking.

You didn’t set out to be a comic actor. Wasn’t your original goal to be a Shakespearean actor?
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 in an experimental version of Macbeth.

Experimental how?
There were two Macbeths. Some other guy played the bad Macbeth and I played the good Macbeth. [laughs]

That seems unnecessarily confusing.
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, that age when everything seems 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.

Was it around this time that you started working as a DJ?
Yeah, I think so. I did it only occasionally, at this 1950s-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 deejayed at the Kansas City bar 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.

You became famous on the bar mitzvah circuit for something called the Donnie the Dweeb dance.
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. I got so slaphappy that I started dancing spastically, kind of mocking the whole thing just to entertain myself. But 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 said, “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 Donnie the Dweeb!” He gave me a name.

What exactly happened during this dance?
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 my shirt off and showing my breasts for a director. That’s how I felt about it. It became kind of a recurring theme for me.

Why did you give up being a bar mitzvah DJ? Did it happen only when your acting career finally took off?
No, it was long before that. I had some friends coming to town, and we were going out to the Magic Castle. I told my boss a month in advance, “I need Saturday night off.” But then the weekend came, and I ended up getting requested for this girl’s party. She really wanted Donnie the Dweeb. So my boss said to me, “Can you just stop by and do the dance? I’ll give you $25 and you can get out of there.”

Did you do it?
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 was Jon Hamm.

From Mad Men?
Yeah, both these guys I’ve known since I was a teenager. They came into town, and I said, “Before we go to the Magic Castle, we need to swing by this party. I just have to do this one quick thing.” So we went, and they had no idea what I was doing. They knew I was a DJ for parties, but they had no clue how bad it had gotten. My boss saw my friends, and he said, “I’ll introduce Paul, and you guys can come in as his henchmen”—I guess because they were wearing suits.

Wait, hold on. You, Jon Hamm and Joe Buck were all in suits?
We had to be, because there’s a dress code at the Magic Castle. So Jon and Joe came out and they were standing to the side, and I pulled 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 gave this teenage girl a retarded lap dance.

Wow. That sounds——

That’s one word to describe it.
It’s the only word! But at this point, I’d become numb to it. After it was all over I walked over to my friends and said, “Okay, guys, let’s go.” Very casual. We went out to the lobby and—I’ll never forget this—Joe Buck looked at me with the most confused expression on his face. He said 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 deejayed again.

Even without the DJ job you weren’t particularly happy in Los Angeles.
I wasn’t.

You once claimed you had a meltdown in the mid-1990s. What happened?
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 as though 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 screw with you. I wanted to do theater. I wanted to do cool indie movies.

It got so frustrating that you painted obscenities on the walls of your apartment.
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 the Northridge earthquake, in 1994, I think, which was 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 would say, “No. What are you talking about?” It was a weird thing. I just didn’t feel sure-footed anymore. A bunch of traumas happened to me in a short 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?” He shot it at me, and I could feel the breeze from the bullet next to my head.

Did it seem Los Angeles was telling you to get out?
Wait, it gets better. I got into five car accidents in just one week.

Five car accidents? How is that possible?
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 did feel like, “Oh yeah, I get it. Message received, universe.”

Why move to New York?
Because in New York you don’t need a car. [laughs]

That can’t be the only reason.
I lived there as a kid. I was born just across the bridge, so it was familiar to me. I’ve always felt safer in New York than 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. Not long after I moved to New York I was cast in this play called The Last Night of Ballyhoo, and I remember walking to rehearsal, holding my script and some coffee, and I just felt so…sane.

You have a son, Jack, who is six, and a daughter, who’s one and a half. Have they seen your movies?
Oh God no. Not yet. But honestly, they’re just not curious. Jack 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 was confusing to him. He’d say, “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.”

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 swearing?
I don’t know. I definitely make an 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. 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 laugh every time. And I know it’s the wrong reaction to have.

It’s certainly not going to discourage him.
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 was like, “In the triangle?” I started laughing and said, “Yeah, that’s it.” And then he was like, “Right in the roof of the house?” I just died.

So your son’s become a guy friend?
That’s it exactly! He’s a dude 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 like the roof of a 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 a year he was obsessed with sprinkler heads. And between the ages of three and five he would dress only in a suit. He wouldn’t leave the house without wearing a coat and tie and dress pants. I remember thinking, This is my dream kid.

How did Jack come to have an Irish pub named after him?
[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 said, “I’m going to build an Irish pub down there, and I’m going to call it Sullivan’s.” Which is Jack’s middle name.

Is that a family name?
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 Light. There would 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.

Did you help him build it?
No, it was a complete secret. He never sent me pictures, never gave me updates. I just knew 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.”

Was it as amazing as you imagined?
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 Schwarz to attend the grand opening of the Brooklyn Bridge. An old New York City police uniform from the late 1800s. A 1936 Olympics document signed by Hitler. Being Jews, we’re all obsessed with Hitler. No Irish pub is complete without some Nazi paraphernalia on the walls.

When did the second pub happen?
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 Julie 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 was 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.

How does it compare with the original?
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 was that I didn’t put in a urinal. But it’s still got some great things I’m really proud of. There are markers in the bathroom so people can write horrible things all over the walls.

Did your dad live long enough to see it?
[Pauses] He didn’t, no. [pauses] It’s funny, 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 he could be co-owner of the pub. [laughs] She and her husband didn’t want Henry to grow up not feeling a part of the family business.

Have your friends and co-­workers seen the pub?
Oh yeah, everybody I’ve worked with has been there. There have been a few live fantasy football drafts, a few poker weekends, a few karaoke parties.

Karaoke is especially popular among comics, isn’t it?
Wildly popular. [Wanderlust director] David Wain is a big fan of karaoke. As are Joe Truglio, Ken Marino, all those guys from Wet Hot American Summer.

Why is that? Is it like AOL e-mail addresses—it’s so uncool that it’s cool?
[Laughs] That may be part of it. When comics get together to do karaoke, it’s not like anybody is trying to be funny. At the same time, nobody is taking it too seriously. It’s hard to explain.

Do you have a favorite karaoke song?
Not at all. That’s a rookie move. I had a karaoke song 10 years ago. Now I like to do ones I’ve never done before.

So what do you look for in a karaoke song? Does it need to be in your vocal range or something more challenging?
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. Everyone I know refers to it as ’raoking. And yes, I do realize how pathetic that sounds.

Don’t apologize.
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 L.A., and Joe and his girlfriend, Beth, and I got a private room. Joe and I like to give each other some surprises. You’ve got to go deep in the book and find something the other person hasn’t heard.

Like what?
The last time I went ’raoking, Joe did “The Worst That Could Happen” by Johnny Maestro and 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 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 going to see the magic happen.