This article originally appeared in the April 2012 issue playboy magazine.
To appreciate the full range of Jon Hamm’s acting ability, you need to watch his sex scenes. As Don Draper, the brooding and tortured advertising executive on Mad Men—which returns in March for its fifth season—he’s had no shortage of sexual dalliances that are, well, brooding and tortured. When Draper gets especially depraved, as he did last season, ordering a prostitute to slap him repeatedly across the face—“Harder,” he insists, “again”—it is not so much erotic fun as the sad self-flagellation of a recently divorced man whose life is slipping away. Compare that with Bridesmaids, last summer’s comedy hit in which Hamm and Kristen Wiig have one of the most ridiculous sex scenes. Hamm’s character initiates all sorts of bizarre and unnecessarily complicated positions, less lovemaking than merciless pounding. Not every actor can do two kinky bedroom scenes and make an audience laugh at one and cringe at the other. But not every actor is Jon Hamm.
Much like George Clooney, Hamm seems to have been born into the world a handsome middle-aged man. But also like Clooney, he had a long road getting there. Matthew Weiner, the creator of Mad Men, claims that after watching Hamm’s audition, he said, “That man was not raised by his parents.” He was partly right. Hamm was born in St. Louis to Deborah, a secretary, and Dan, who ran the family trucking business. The couple divorced when Hamm was two, and he lived with his mother until she succumbed to abdominal cancer just eight years later. He moved in with his father, who passed away from diabetes on New Year’s Day 1991 while Hamm was studying at the University of Texas. By 20 he was an orphan without many prospects. He transferred to the University of Missouri and immersed himself in theater, doing 15 plays in just two years. In 1995 he moved to Los Angeles with $150 in his pocket and dreams of being a Hollywood actor.
Hamm had some minor success at first, winning small roles on TV shows including The Division and Providence. Friends gave him work whenever they could—he had a walk-on role as a cable guy on The Sarah Silverman Program. And his girlfriend, Jennifer Westfeldt, cast him in the 2001 indie comedy Kissing Jessica Stein, which she co-wrote and starred in. But for several years Hamm was just an occasionally employed actor who waited tables to pay his bills—by his own account, “not the horse you wanted to bet on.” At least until 2007, when Mad Men made him a star virtually overnight.
Hamm used his newfound fame to prove his range. Whether hosting Saturday Night Live or playing Tina Fey’s clueless yet dreamy pediatrician boyfriend on 30 Rock, he’s surprisingly comfortable delivering a punch line. As Fey explains, “Jon Hamm has the comedy skills of an SNL cast member, the exoskeleton of an Arrow shirt model and the gratitude and work ethic of a person who got famous after the age of 30.” This month the 41-year-old Hamm takes another stab at comedy with the movie Friends With Kids, directed by and co-starring Westfeldt.
We sent writer Eric Spitznagel, who recently interviewed Craig Ferguson and Paul Rudd for playboy, to talk with Hamm at the Chateau Marmont in West Hollywood. He reports: “I was hoping he’d want to partake in some afternoon recreational drinking, maybe even downing a few of Don Draper’s signature old-fashioned cocktails. But instead he drank Diet Cokes and nibbled on an iceberg lettuce wedge. At one point he wandered over to the next table to give a back massage to his friend, author and Daily Show correspondent John Hodgman, who was dining with indie rockers Aimee Mann and John Roderick. Hodgman introduced himself as Hamm’s ‘personal trainer’ and insisted that the Mad Men star wear a full tuxedo for their workout later that day. ‘No problem,’ Hamm responded without cracking a smile.”
For a while it looked as if you might lose your job. Contract negotiations between Mad Men creator Matthew Weiner and AMC delayed the fifth season for about a year, and there was some speculation that the show wouldn’t return. Was the wait frustrating? The truth is it wasn’t Matt’s negotiations that took long. The protracted negotiations were between the studio and the network. In the world of network television, there is a very large pie, and the studio and the network get the biggest pieces of that pie. The rest of it is crumbs. They’re nice crumbs, don’t get me wrong. But they’re the crumbs that start with t and m rather than b. When corporations fight, it generally takes a long time. There are a lot of lawyers. The minute you start taking that shit personally, you’ve lost.
But as an actor who just wanted to get back to work, did you worry it was ruining the show’s momentum? A year is a long time to make an audience wait.
I wasn’t worried. I think we’ve done a nice job over the past four years of establishing and growing an audience, and hopefully absence makes the heart grow fonder. If nothing else, we got to hang out with our families a little longer.
On 30 Rock Alec Baldwin once said that beautiful people live in a bubble of free drinks, kindness and outdoor sex. He was referring to your character, a dumb but attractive doctor named Drew Baird, but do those same rules apply to you?
To Drew Baird, absolutely. To me, not so much.
When was the last time you had outdoor sex?
It’s been a while. In the era of TMZ, I don’t think outdoor sex is a particularly good idea. It’s one of those things that sound way better than they actually are. There’s something not sexy about all the twigs and bugs and sand. You end up with stuff in places you don’t want it. It always looks better in the well-lit Skinemax version.
What about free drinks? Have you paid for a drink since Mad Men became a hit?
I am a big tab getter. I’ve been the beneficiary of other people’s good fortune for a long time in my life, so I feel it’s karmic payback. But I’ve definitely had people offer to buy me drinks. It kind of comes with the territory when you play a hard-drinking character on TV. It’s never a bad thing, at least for guys. If you’re a girl, it would probably be a bit creepy and weird if strangers kept trying to buy you drinks. But for guys it’s usually just some bro who wants to say he did it.
Due in part to the success of our show, the world of specialty cocktails has grown up. It’s easier to find a fancy bar where the bartender takes 10 minutes to make one drink.
Don Draper enjoys the brown liquors. Do you indulge?
Oh sure. Never at work, but it is a time-honored tradition to celebrate your work upon completion. I live in a neighborhood that has a nice bar with off-the-beaten-track labels, so you can be adventurous and try something new every night. In the past four years or so, due in no small part to the success of our show, I think the world of specialty cocktails has grown up. It’s a lot easier to find a fancy bar where the bartender takes 10 minutes to make one drink. There are a ton of places in L.A. that do that now.
What’s the manliest thing you’ve ever done? Have you ever overhauled a car engine or popped a dislocated shoulder back after an injury?
No, but I got hurt once shooting Mad Men.
What? How is that possible?
I know, it’s kind of ridiculous. It’s not exactly the most stunt-heavy show. We were shooting the Korea flashback. There was an explosion, and I sort of dove through the frame. The first time we did it, I broke my right hand at the base of my pinkie. I heard it click and went, “Well, that’s broken.” And then the second time——
You hurt yourself twice?
The first time was in rehearsals. We did it again for real, and instead of landing on my broken hand, which hurt tremendously, I landed on my left shoulder and kind of separated it. I’ve had a lot of injuries on this show, which is strange given the nature of it.
By “a lot of injuries,” what are we talking about exactly?
I’ve gone to the hospital twice. [laughs] I know, I know, it’s embarrassing. During the first season, a piece of the set fell on my head and I got seven stitches. I think it says less about the show than it does about my durability and age.
After four seasons of playing Don Draper, does hedonism seem fun to you anymore?
I think we’ve tried to portray that lifestyle accurately. A three-martini lunch is fun in theory. And it’s fun to look cool while you’re staring out of windows, drinking scotch and smoking. But the reality is, if you have a three-martini lunch, you don’t get much done in the afternoon. And if you stare out the window and smoke too much, you get fucking lung cancer.
Does Don still derive genuine joy from all the booze and recreational sex? Or did he ever?
I remember something a friend’s dad said once. When the ritual becomes habitual, then you’ve lost the mystery and the fun of it. I do think the chemicals that Don ingests are a means to an end. It’s a way for him to maintain his energy and enthusiasm for living. But as with any addiction, there’s a law of diminishing returns. You never get the buzz you got the first time.
For all the bad things about Don, he has some admirable qualities, such as his reticence. Is there power in being quiet and not revealing everything about yourself?
I definitely think there is, and it’s something I try to imitate—which is weird to say as I’m being interviewed for a national magazine. I understand the irony there, or at least the hypocrisy.
In your defense, doing interviews is part of your job.
Yes, there’s that. But it’s hard to escape the fact that we live in a world where everybody is clamoring for attention and people think their life doesn’t matter if they’re not on TV or the paparazzi aren’t following them. They don’t feel validated unless there’s a lens on them or they’re tweeting so more people can hear what they have to say, which all contributes to a vast echo chamber that serves basically to turn everything into noise. Eventually your life is lived in sound bites and reality shows and 140 characters, becoming smaller and smaller without any nuance or deeper reflective quality. I try to get away from that and listen more than I talk, except of course in this situation.
Do you have the emotional stoicism of Don Draper, or are you a heart-on-your-sleeve kind of guy? Will you cry at a sad movie?
It depends on the movie. This is by turns hilarious and embarrassing, but I’ll tell it anyway. I cried at Marley & Me. Not just teared up a little but full-on cried. That was a fucking nightmare. Dead-dog stories always get me. And dead-mom stories—Terms of Endearment, stuff like that. If a parent dies in a movie, I’m a fucking wreck.
Because it relates to your own life?
Oh sure, absolutely. I mean, come on, I’m not made of stone.
Your mother died when you were 10 years old. You were so young; did you even realize what was happening?
There was not much awareness. When you’re 10 you’re kind of cognizant of how the world works, but it’s through the filter of a child. There’s definitely no sense of the permanence of death or the meaning of not being able to see someone or talk to someone again, especially someone as important as your mother.
She died of cancer?
Advanced abdominal cancer. It started in her colon and then rapidly spread, as cancer does. This was in the late 1970s, early 1980s, when there was no early detection, no MRIs. They basically opened you up and went, “Oh shit.” They didn’t even realize she had cancer until it was very advanced. As such, it was a quick but probably very painful death. And it was hard to watch, because she basically shriveled up. She passed away when she was 35, so she was not a frail old lady. This was a woman essentially in her prime.
Do you remember anything about her last days, or is it just a blur?
Mostly it’s a collection of images of other people in my family losing their shit. My dad, my grandfather, my grandmother, my aunts, all of them just breaking down around me. And I was thinking, What’s happening? What’s going on? Just recently the father of a close friend of ours passed away suddenly, in an accidental, shocking way. My friend had two boys, and I asked how they were doing. And I was told, “They don’t know. I don’t think they have a real concept of it.” When I talked to the older one, who’s eight, it was obvious he knew that I was sad and wanted to help. He wanted to make me happy. And that’s what I was like when my mom died. I was the kid who said, “Come on, Dad, let’s take a drive. Let’s go do something.” I didn’t have the capacity to understand that I was sad, but I could recognize it in others. “Come on, Grandpa, let’s go fishing.” That kind of thing. That’s what it was all about or at least what I remember about it. It was a long time ago.
Your father passed away 10 years later, when you were in college. Was that easier or harder?
It was worse in many ways. By the time you’re 20, you have a sense of mortality. You still think you’re bulletproof, but you do have this realization that things end, and sometimes they don’t end well. So that was particularly hard. It was also worse because that was my last parent. When you’re a kid you think, Well, somebody will take care of me. I’ll land on my feet somewhere. As long as there’s Atari, something is bound to happen. But when you’re 20 things are significantly different and significantly harder. I’m certainly not ranking which parent I loved more, but it was different.
Sometimes life doesn’t play out the way you’d like. I’m not a big ‘everything happens for a reason’ guy, because that suggests there’s more order in life than there is. But things happen, and there are consequences.
You were officially an orphan.
Exactly. You’re on your own. But that’s life; that’s the way it is. Sometimes it doesn’t play out the way you’d like. I’m not a big “everything happens for a reason” guy, because that suggests there’s way more order in life than I think there is. But things happen, and there are consequences. And life is dealing with those consequences.
If your parents had lived, would your life have gone in a different direction?
One hundred percent. Absolutely.
Would you have been an actor?
I don’t know. I think anybody who chooses any kind of career in the arts—and I’m using that term loosely for what I do—comes from a place of being a little bit unmoored. If I had grown up in a two-parent household and had parents telling me what to do, I’m sure their first piece of advice would not have been “You should be an actor. You should move to L.A. with no money. That sounds like the best plan.”
There was a moment during the production of Mad Men when you looked at yourself in the mirror of your dressing room, dressed in Don Draper’s suit, and realized that the character looked a lot like your dad. What were the similarities?
It was the costume. There was an aha moment of seeing myself in all that gear and realizing I looked exactly like my father. I mean, I look like my father anyway. I have a little more hair than he did, and I’m a little skinnier. He was a big guy; his nickname was the Whale, so you can imagine. Other than that, I’m a pretty good likeness. But there was something about the suit. I remember his closet was filled with suits in every style and color, like a rainbow of linen and cotton. That’s what he wore; that was his uniform.
Do you still use your dad as inspiration for Don Draper?
Sometimes. Maybe not consciously, but it’s there; it’s always there. I think about my dad a lot. He was in the trucking industry, which was far less glamorous than the advertising industry. There were a few more Teamsters involved. He was a third-generation part of the business. My dad’s grandfather, my great-grandfather, started it with basically a horse and a wagon in the late 19th century. When my grandfather took over, in the 1940s and 1950s, it was all about interstate trucking, with 18-wheelers and big rigs. By the time my dad got the business, in the late 1960s and 1970s, everything had changed. The business model had drastically shifted. It’s like the way Blockbuster became irrelevant overnight because of Netflix. There are still video stores but not the way there were in the 1980s and 1990s. That’s what happened to the trucking industry. Container shipping became significantly cheaper, and air freight was significantly cheaper. It was much easier to get stuff places, so you didn’t have to depend on trucks anymore. My father basically inherited a business during its decline, which probably didn’t feel good.
Did you ever ask him about it?
He died when I was 20, so I didn’t have a lot of adult conversations with him. I didn’t have the time.
Or the emotional maturity, probably.
It wasn’t what I was thinking about at 17. “Hey, Dad, tell me about your business.” I had homework to do and girls to not make out with.
If you had a chance to have a conversation with your father or your mother today, what would you ask them?
[Pauses] That’s an interesting question. I think about it all the time. [pauses] I guess I’d just ask about their lives. The hard part of having an adult life when your parents aren’t around is not having that adult wisdom that I think is incredibly useful as a human being. There are times, even when things are going well, when you can’t help but think that you’re some kind of giant fuckup. But if you had a parent who could say, “Seriously? You think you’re fucked-up? That’s nothing!” And then they’d tell you about all the mistakes and bad life decisions they made at your age. I think that would make a huge difference for me. I’d be like, All right, I feel better. They screwed things up so much more than I did, and they turned out okay.
If it had been an option, could you see yourself being the fourth generation in your family’s business?
I’m pretty glad I didn’t have to follow in my dad’s footsteps, because I would be the worst salesman on the planet. I don’t have that gene. I have a lot of friends who are salesmen, and they’re constantly on. It’s like a stand-up comic who always has to have material at the ready. I’m just not able to do it.
But you sell yourself in auditions, right?
I suppose I do. They’re the worst things in the world. I’m sure there are more humiliating ways to torture yourself, but I haven’t experienced them. It’s the rare person who’s good at auditioning, who can just come in and do their thing and leave and still have self-respect and dignity. I’m not one of them.
Didn’t you audition six times for Mad Men?
It was at least six, so I had every level of opportunity to be humiliated. Matt tells this story now that he knew I was perfect for Don Draper after the first audition. My response to that is, Well, I wish he had fucking told me. It would’ve made me feel a lot better.
Why didn’t he tell you?
Because it wasn’t entirely his decision. There are studios and networks to be appeased. That’s the way the sausage is made. All it takes is one person who just goes [makes a fart noise and thumbs-down]. If they’re powerful enough, it ends. You could have five of the greatest auditions you’ve ever had, and in the sixth you’re a little off your game, or the guy had a bad piece of fish at lunch and doesn’t like anything, and it’s over.
You’ve said you were at the bottom of their list of actors. How did you know?
I’d been around long enough; I knew how these things worked. You go to the sign-in sheet and see 15 people have been there before you, and they’re recognizable names. At the time I remember thinking, It would be nice if they cast me, but they’ll probably just cast the movie star who kind of looks like me. It was surreal. Every day I was sitting in the room, waiting to audition, and there were nine guys who looked exactly like me but with longer résumés.
How did you find out you had the job?
It’s actually a funny story. I was at their production office in Manhattan with Matt, and he told me, “I want you to walk around this office like you have the part.” I thought, I’d much rather walk around like I have the part because I have the part, but okay. He was introducing me to all the department heads, saying things like “This is Don.” I said, “Don’t say that. You’ll jinx it!” We ended up going across the street to the Hotel Gansevoort. They have a roof deck, and it was a pretty spring day. Matt and I had a few drinks with the network brass. Then we were riding down in the elevator, and the woman in charge of making the decisions said, “You probably know this by now, but you’ve got the job.” In the elevator with us was Franz Beckenbauer, who was a pretty famous European soccer player in the 1970s. He’s a coach or manager or something now. Literally the moment they told me I got it, the elevator opened and the lobby was filled with photographers. The lights were flashing and people were rushing toward us, shouting, “Oh my God, oh my God!”
Did you think all the attention was for you?
For a split second. I was still on the adrenaline rush of getting the part. But nope, it was just some excited Germans who wanted to meet their soccer hero.
Your first play was a first-grade production of Winnie-the-Pooh.
That’s right. I played the titular character.
Can you give us a taste? Was your Winnie goofy and bumbling or confident and soft-spoken?
It was more bumbling. It wasn’t that nuanced. My mom made the costume out of a Butterick pattern, and I had a pillow taped to my belly. I tumbled around and tried not to knock the set over. A VHS tape of this play does exist, by the way.
It’s out there somewhere?
Oh, I know exactly where it is. And it’s not going anywhere.
Did you have to fight for the role like you fought to play Don Draper?
No, it was pretty easy. The teacher assigned everything, and I think I was picked to be the main guy because I was the only one who wasn’t terrified of standing in front of an audience and looking like a moron. Everybody else just wanted to be trees.
In high school you were both a jock and a theater kid, right?
That’s right. I played football and baseball, and I also did as many plays as I could.
Those two worlds don’t often intermingle, especially in high school. Did your jock friends give you grief about doing plays, or vice versa?
I went to a progressive school in St. Louis, the John Burroughs School, that was founded on John Dewey’s principle that education is experience. You’re supposed to experience as much as you can. My teachers said, “Listen, we’re not all good at everything, but you never know. Maybe you’ll like painting, so try it. Maybe industrial design is going to be your jam.” There was a theater teacher, Wayne Salomon, who was a big believer in getting the football players to do plays. He’d tell us, “It’ll look good on your college résumé.” There was no stigma attached to it. Nobody would say, “You’re doing theater? Oh, you’re gay.” And that’s huge for teenagers, because at that age everything is microanalyzed.
It’s a big age for self-doubt.
Exactly. What will Sarah think if I do this? A typical teenager’s whole world is caught up in that swirl of overthinking, but that was removed from the equation for us. Theater was just a fun thing to do, and I think that’s why I stuck with it for so long.
Were sports also just a fun thing to do, or did you ever consider going pro?
At a certain point you realize, or at least I realized, that you can take athletics only so far. I’m a good athlete. I’m coordinated and can do a lot of things, but I’m certainly not at the elite level. And honestly I had no real drive or desire to put the time and effort into honing that skill. I played football in high school and was recruited by a lot of colleges, but they told me things like “You’ve got to put on 60 pounds and work out every day.” I said, “Nope, not going to do that.” I was also a pretty good baseball player and had some interesting offers, but they said I’d have to spend three hours a day in the cage. I just wasn’t interested. It’s repetitive and boring and I don’t want to do that. I gravitated toward theater because it mixed things up. And the students who did theater were very much my people.
In what way?
Go to any theater department in the country and it’s usually made up of the outcasts and the misfits and the orphans. It’s like, “Come on in; we’re always open.” It’s the Island of Misfit Toys. It’s a place where they can express themselves, and it’s welcoming and not exclusionary. There’s plenty of time to be made to feel like shit once you get to Hollywood. [laughs]
You moved to Los Angeles in the mid-1990s with just $150 in your pocket. Did you seriously think that would be enough?
Well, it was all I had in the world. And I had some credit cards that were on the way to being declined. My mom’s younger sister lived in L.A., and I called her and said, “Hey, if I can make my way out there, can I stay with you for a little bit?” She said, “Absolutely,” so I knew all I had to do was get out here. This was in an era of significantly cheaper gasoline. I drove a 1986 Toyota Corolla that had pretty good mileage. I had stops planned along the route where I had friends I could stay with and get a bed, a shower and free food.
That must have been quite a trip for you to remember every leg of it more than 15 years later.
I just love road trips. I love driving and maps. This was in an era way before CDs and satellite radio, back when you could tune in to AM radio and find some weird station to listen to for a few hours. I loved it all. And the plan worked great, with the exception of my friend in Carlin, Nevada. Turned out he’d moved and forgot to mention it to me. I didn’t have a cell phone, obviously, so I didn’t find out until I tried to call him from a gas station and his phone had been disconnected. So I slept on the side of the road. But I made it to Los Angeles and somehow my $150 lasted. I pulled into town on Thanksgiving Day.
Just in time for dinner?
Well, my aunt and uncle had plans elsewhere, so I actually showed up at an empty house.
That sounds vaguely depressing.
It wasn’t. I was happy just to be there. The first thing I did was call all my friends back home. I was like, “It’s 85 degrees here! I’m sitting outside on a porch!” Then I went to an orphans’ Thanksgiving hosted by a friend my aunt and I both knew from St. Louis. Coincidentally, one of the people at the dinner was Kevin Williamson, who had just sold a script called Scary Movie, which would later become Scream. So that was my intro to L.A.
And then came the hard part.
Exactly, yeah. Then it was time to find a job, an agent, a place to live and all that shit, none of which came easily. I called people I knew. I called Paul Rudd, who I knew from college, and said, “I’m going to ask this only once, because I don’t want to be that guy. I need a favor. Can you give me one person to call who will take my call?” He gave me a number, and that meeting turned into another meeting, which turned into another meeting. The dominoes started falling and I eventually got an agent, and then I didn’t work for three years and my agent fired me.
Do you have any perspective in hindsight? Why couldn’t you break through?
It was just bad timing. This was in the late 1990s, when teen dramas like Dawson’s Creek were popular. I was out of sync with what the market was looking for. They wanted bright, bubbly and young. I was none of those things. I mean, I was young. I was only in my mid-20s, but I didn’t look young.
You were too young to play the parents but too old-looking to play the teenagers.
Right. I was in between the two camps. I remember I went to an audition and Peter Gallagher was there trying out for the same role. I was like, “Are you kidding me? I’m 27! No offense meant to Gallagher, but come on, man. Why am I here?” It was depressing. So I was dropped by my agent, got cast in a play and got another agent. That agent got me my first real job, that job turned into a longer job, and on and on. It was a slow process and there was a lot of wheel spinning.
Did you have a plan B, in case acting didn’t work out?
Not really. I came to L.A. when I was 25 and I made the decision that if I didn’t get a job that sustained me by the time I was 30 I would go back home. That’s five years, which at that point was 17 percent of my life. In my opinion that was more than enough time to give it a legitimate shot.
Did you make your deadline?
I did it in three. By the time I was 30, I was getting regular jobs. On my 30th birthday I was working on a movie called We Were Soldiers, with Mel Gibson. I was at a hotel room in Columbus, Georgia.
How did you celebrate?
My girlfriend, [actress] Jennifer Westfeldt, came down. She was in New York at the time, probably working on a play. She came to visit and flew down three of my good friends. It was a pretty great birthday. I thought, Yeah, man, this is it. This is the best of everything right here.
Were you comfortable enough with your acting career to quit waiting tables?
I’d quit about a year earlier. It was weirdly hard to give up.
Why? Did you still need the money?
No, but it was a part of my identity. To this day it’s the thing I’ve done the most in my life. It’s the job I’ve had the longest. I have no shame about that. It’s something I’m always ready to go back to. I’m comfortable behind a bar, and I’m comfortable wearing an apron. It doesn’t bum me out. I’m totally fine with it. There will always be restaurants and bars. There’s no possible way to wreck that with e-commerce. It will never be replaced by the internet. Restaurants and bars are some of the last truly safe businesses left. Video stores, clothing stores, record shops, newspapers and TV shows—everything disappears and ends up on the computer. But not restaurants. There are definitely worse day jobs to have.
What was the worst for you?
I did set dressing on some soft-core porn films. That was hands down the worst. I was working on the crew from seven to seven, and it was horribly depressing.
Set dressing, as in props?
Yeah, the props. I was essentially an extension of the prop department. I also did continuity, which means I had to make sure that if an ashtray was on the corner of a table in one scene, it was there in another. I’m sure there are more terrible day jobs in L.A., but it’s definitely on the lower end of the spectrum of the wonder of moviemaking. It wasn’t even that much money, but it was money. A friend of mine from college had done it and was too depressed to go back. She told me, “I literally cannot do this anymore.” I was like, “I’ll do it!” And I got the same way in about a month.
Your social life at the time consisted of going to comedy clubs and befriending comedians. How did you end up in that world?
There’s a club in L.A. called Largo, and Mondays at Largo were the hottest nights in town for comedy, or at least for the particular brand of comedy that I liked. It was an underground, hipster comedy scene, with Sarah Silverman, Paul F. Tompkins and Patton Oswalt. And it was $5 to get in. It was cheaper than the nightclubs, which I hated anyway. The drinks at L.A. nightclubs were too expensive and the music was too loud. At Largo there was no drink minimum, and you got two and a half hours of great entertainment. I slowly ingratiated myself into that world by hanging around all the time.
You became good friends with many of the performers, like Zach Galifianakis.
Yeah, I know all those guys. It’s weird that everybody in that social circle came up around the same trajectory. Zach is monumentally famous now, and he’s still the same guy I’ve always known. I look at him and say, “This thing happened to you.” And he just smiles back at me and says, “The same fucking thing happened to you.” I don’t see it because I’m looking outward rather than in. But it is true, and it’s funny.
What’s it like socializing with comics? Are they shy and reserved, or is it a nonstop barrage of jokes?
All of the above. And if it’s the latter, I generally don’t participate. I learned a long time ago never to get into joke-telling competitions with professional joke tellers. We talked about this earlier, but there’s a lot to be said for just being quiet and listening. I love being around comedy people and listening and laughing. It’s therapeutic.
But you can hold you own with comics. You were hilarious on 30 Rock.
I definitely felt over my head on that show. My approach to comedy has basically been to stand next to really funny people and try to keep a straight face.
You’re being humble. What about that sex scene with Kristen Wiig in Bridesmaids? You definitely weren’t just keeping a straight face there.
No, I guess not. [laughs]
When you’re doing an outrageous sex scene, do you feel embarrassed, or are you too caught up in the moment?
It’s like running in the rain. There’s a certain point when you go, “Fuck it, I’m already wet. I’m not going to get any less wet, so I might as well just enjoy how this feels.” I mean, sure, there’s an awkwardness about being in a weird flesh-colored thong, bouncing on top of an actress. And I am not a small human being. I weigh at least 200 pounds and I’m six-foot-two. And Wiig is a twig; she’s a skinny little thing. I told her, “Just punch me in the side if I’m hurting you.” It’s weird and uncomfortable at first, but then all the awkwardness melts away and you think, All right, we’re doing this, so let’s have fun with it. You know what I mean? You’re in that moment and it’s happening and it’s not going to get any better, so you might as well enjoy it.
This industry is populated by a lot of narcissistic, mean-spirited, horrible people who get rewarded for being narcissistic, mean-spirited and horrible.
After Mad Men ends, will you focus more on comedy or drama? Or does it matter?
It doesn’t matter. I don’t have a preference either way. All I care about is working with people I enjoy being around. I’ve been fortunate in that I have not worked with many douche bags. And this industry is populated by a lot of narcissistic, mean-spirited, horrible people who get rewarded for being narcissistic, mean-spirited and horrible. Thus far I’ve been able to keep my exposure to that crowd to a minimum.
It probably helps when you collaborate with people like your girlfriend.
Yeah, I already know she’s none of those things. She’s the least narcissistic, mean-spirited person I know.
You and Westfeldt have a new movie, Friends With Kids.
When you don’t have children and you make a movie about the fear of having children, it practically begs to be read into.
[Laughs] Oh sure, I understand that. And there is some autobiography to it. We’ve seen enough of our friends, who shall obviously remain nameless, become parents, and sometimes it’s hard not to think they shouldn’t have had kids.
Because it’s a bigger responsibility than they’re ready for?
That’s what it seems like. Maybe they should’ve waited. But if you wait until you’re ready to have kids, then it’s possible you’ll never have kids. The unspoken corollary to that is, maybe some people shouldn’t have kids. Which you’re not allowed to say because people get offended.
Is it safe to assume you don’t want children?
I don’t have a driving force to have a baby. That said, I’m in a committed relationship, and if it ever came up, I’m not ruling it out. There’s a reason it hasn’t been prioritized, because I don’t think either of us has that pull. I don’t know; it could happen tomorrow. I have no clue.
What about marriage? Have either you or Westfeldt actually said, “Let’s not get married”? Or is it a mutual understanding?
It was never a discussion. I think marriage often is an arrangement between families more than an arrangement between the two people involved. I don’t have a particularly defined example of marriage in my life. My parents got divorced when I was two and never remarried. So it doesn’t mean anything to me. I don’t mean to say that it shouldn’t mean things to other people. I’m not judging it one way or another. It’s just my experience. I don’t have that paragon of married life to look at and think, Oh yeah, that’s it! That’s what I want!
Don Draper once said, “What you call love was invented by guys like me to sell nylons.” Do you think there’s maybe some truth to that?
I hope not. I don’t think so. Don has had a lot of great ideas, but that’s not one of them. [laughs] The minute you start modeling your love life—any part of your life, actually—after Don Draper, I think you’re in trouble.
Draper took his identity from a dead solider in Korea. If you could do the same thing and become somebody else, take their name and identity and start over, who would it be?
[Pauses] I guess my answer would have to be nobody. It’s an attractive idea, but as I think our show points out, it’s a double-edged sword. I mean, I wish I was a professional baseball player, but I don’t want to change places with one. I wouldn’t mind being the secretary-general of the United Nations, but I wouldn’t want to change places with him. For a day maybe, but I’ve lived in this skin for 40 years now, and I’m getting kind of used to it.