To truly 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 guru on Mad Men — which returned in mid-March for its fifth season on AMC — he’s had no shortage of sexual dalliances that were, 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 insisted. “Again.” — it was less erotic fun than the sad self-flagellation of a recently divorced man whose life was slipping away. Compare that to Bridesmaids, last summer’s comedy movie blockbuster in which Hamm and Kristen Wiig had one of the most ridiculous sex scenes in recent memory. Less lovemaking than merciless pounding, Hamm’s character initiates all sorts of bizarre and unnecessarily complicated positions, from the “Creepy Crab” to “Rock the Cradle.” At one point he mutters to Wiig “let me drive the bus” and then snaps her bra-strap, giggling maniacally. Not every actor can do two kinky bedroom scenes and make an audience laugh one time and cringe the next. But not every actor is Jon Hamm.


Much like George Clooney, Hamm seems to have been born into the world as a handsome middle-aged leading man with an expressive furrowed brow. But also like Clooney, it was a long road to get there. Matthew Weiner, the creator and head writer for Mad Men, claims that after watching Hamm’s audition, he turned to his casting director and said “That man was not raised by his parents.” He was only partly right. Hamm was born in St. Louis and raised for at least his formative years by his biological parents; Deborah, a secretary, and Daniel, the third-generation proprietor of 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 shortly after his father’s death and immersed himself in theater, doing fifteen 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 but recurring roles on TV shows like The Division and Providence. Friends like comedian Sarah Silverman gave him work whenever they could — he had a walk-on role as a cable guy on The Sarah Silverman Program, where he wore an almost indecipherable badge that read “Eatin’ All the Pussy Since ’92.” And his longtime girlfriend, Jennifer Westfeldt, cast him in the 2001 indie romantic comedy Kissing Jessica Stein, which she wrote and starred in. But for well over a decade, 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 took the world by storm, and Hamm became a sex symbol virtually overnight. One minute he was just another unknown struggling actor, and the next he was the living embodiment of hard-drinking, chain-smoking, spouse-cheating 60s nostalgia.

Most actors would’ve been fine if their legacy began and ended with Mad Men, but Hamm used his newfound fame to prove that he was more than a one-trick pony. Whether he’s hawking “Jon Hamm’s John Ham” — the ham you can eat in the bathroom — in a commercial parody for Saturday Night Live (he’s hosted the show three times) or playing the clueless-yet-dreamy pediatrician boyfriend of Liz Lemon (Tina Fey) on NBC’s 30 Rock, he’s surprisingly comfortable delivering a punchline. As Tina Fey explains it, “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 thirty.” This month, the now 41-year-old Hamm will take another stab at comedy with the movie Friends With Kids, co-produced and co-starring his girlfriend Westfeldt, about the anxieties of being middle-aged and childless; a subject that Hamm and Westfeldt, both middle-aged and childless, know something about.

We sent writer Eric Spitznagel, who recently interviewed Craig Ferguson and Paul Rudd for Playboy, to talk with Hamm at the Chateau Marmont in 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. Not exactly bacchanalian stuff. He did, however, wander over to the next table to give a back massage to his friend, author and Daily Show corespondent 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.”

PLAYBOY: Your Mad Men co-star John Slattery has been spreading rumors that you’re a piano prodigy. Apparently it’s a talent that only comes out after you’ve had a few drinks. Is he pulling our legs?

HAMM: (Laughs.) He is, yes. He’s perpetuated this myth that somehow I am a really great piano player. But I can not nor have I ever played the piano, no matter how drunk I get. Nothing could be further from the truth. I don’t know when the rumor started, but I guess John told a reporter, “This guy Jon Hamm is just a brilliant piano player.” And it got traction because people of course believe everything they read, and John said it with such conviction. But no, that’s a complete fabrication. John is something of a prankster.

PLAYBOY: That can’t be the only time he’s messed with you. You directed your first episode of Mad Men this season. Did Slattery do anything to make your job more difficult?

HAMM: He tried. The second shot we did for that episode was a scene with John and Elisabeth (Moss). They tried to play a hilarious prank on me, and then right before it happened, one of them, I will not say whom, bailed on it, leaving the other one in the lurch. So they failed.

PLAYBOY: What was the prank?

HAMM: They were going to try and ruin a take with some on-purpose bad acting. I don’t know exactly what, whether they were going to talk too soft or too loudly. But it was something like that. They were basically conspiring to do it badly. It would have been pretty effective had they stuck to it.

PLAYBOY: Were you nervous to try directing?

HAMM: I wouldn’t say nervous, It was more of a weird out-of-body thing. Especially when you’re watching yourself on the monitor. As a director, you’re trying to evaluate the scene, and there were times when it was like, “Oh, that’s terrible. That actor really needs to learn how to… Oh, wait, that’s me.” (Laughs.) Any nervousness came way before we started shooting, in prep, when you’re looking at everything that needs to be done. You just take it one step at a time until you make it to the top of the mountain. I’ve taken that approach from the beginning with this show. Not just with directing, but everything about doing it. It can be overwhelming. I don’t mean to make it sound like it’s the hardest job on the planet. I’m not a coal miner. It could be a lot worse. This is a pretty great job and I’m glad to have it.

PLAYBOY: For awhile it looked like you might lose it. Contract negotiations between Mad Men creator Matt Weiner and AMC delayed the fifth season for well over a year, and there was some speculation that the show wouldn’t return. Was the wait frustrating?

HAMM: The truth behind all that is that 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 literally crumbs. They’re nice crumbs, don’t get me wrong. But they’re the crumbs that start with T’s and M’s rather than B’s. 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.

PLAYBOY: But as an actor who just wanted to get back to work, did you ever worry that it was ruining the show’s momentum? A year is a long time to make an audience wait.

HAMM: I wasn’t worried. I think we’ve done a nice job over the last 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.

PLAYBOY: Weiner has said that Mad Men will only run for three more seasons. Has he told you how it ends?

HAMM: Yeah, but just the broad strokes. I don’t want to know specifics because I’m deathly afraid of playing to the end. I just want the shades and colors, not specific plot points.

PLAYBOY: 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?

HAMM: To Drew Baird, absolutely. To me, not so much.

PLAYBOY: When was the last time you had outdoor sex?

HAMM: It’s been awhile. In the era of TMZ, I don’t think outdoor sex is a particularly good idea. It’s one of those things that sounds way better than it actually is. There’s something not sexy about all the twigs and bugs and sand. You just end up with stuff in places you don’t want it. It always looks better in the well-lit Skinemax version.

PLAYBOY: What about free drinks? Have you paid for a drink since Mad Men became a hit?

HAMM: I am a big tab getter. I have been the beneficiary of other people’s good fortune for a long time in my life, so I feel like it’s a karmic payback thing. 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’d 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.

PLAYBOY: Do you take every drink that’s given to you or do you dump it out when they’re not looking?

HAMM: Sometimes I’ll politely decline, especially if I’m already in my cups. I’ll be like, “Man, I’m sorry, I’ve got to work tomorrow.” And also, sometimes you want to make sure that you’re watching the bartender make it. You know what I mean?

PLAYBOY: So nobody slips you a roofie?

HAMM: Or whatever. It’s such a weird world we live in now. But I usually assume that if somebody buys you a drink, they mean it as a nice gesture. I’m a bit pollyannaish in that regard. I think most people are fundamentally good. I don’t look for sinister motivations everywhere.

PLAYBOY: Don Draper enjoys the brown liquors. Do you indulge?

HAMM: 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 very nice bar with off-the-beaten-track labels, so you can be adventurous and try something new every night. In the last four years or so, due in no small part to the success of our show, I think the world of specialty cocktails has really grown up. It’s a lot easier to find a fancy bar where the bartender takes ten minutes to make one drink. There are a ton of places in LA that do that now.

PLAYBOY: When hosting Saturday Night Live, you’ve thanked the cast with a gift that would’ve made Don Draper proud.

HAMM: That’s right, yeah. My gift to the writers and cast has always been bourbon. I’ll truck in ten, fifteen cases or however much it is, to get everyone a bottle of whatever the bourbon of my particular fancy is that week. It’s been fun. It’s something that most people can appreciate, and it’s usually a nice looking bottle, so if they don’t want to drink it they can stick it on the shelf.

PLAYBOY: What’s the manliest thing you’ve ever done? Have you ever overhauled a car engine or popped a dislocated shoulder back in after an injury?

HAMM: Not really, no. I got hurt once shooting Mad Men.

PLAYBOY: What? How is that possible?

HAMM: I know, it’s kind of ridiculous. It’s not exactly the most stunt heavy show. We were shooting the Korea flashback and there’s 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-

PLAYBOY: You hurt yourself twice?

HAMM: 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 very strange given the nature of it.

PLAYBOY: By “a lot of injuries,” what are we talking about exactly?

HAMM: 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.

PLAYBOY: After four seasons of playing Don Draper, does hedonism seem as fun to you anymore?

HAMM: I think what we’ve tried to do is 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 and 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.

PLAYBOY: Does Don get genuine joy anymore from all the booze and recreational sex? Or did he ever?

HAMM: I remember something one of my friend’s dads 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 addict, there’s a law of diminishing returns. You never get the buzz that you got the first time.

PLAYBOY: For all the bad things about Don, he also has some admirable qualities, like his reticence. Is there power in being quiet and not revealing everything about yourself?

HAMM: I definitely think there is, and it’s something I try to imitate. Which is weird to say while I’m being interviewed for a national magazine. I understand the irony there, or at least the hypocrisy.

PLAYBOY: In your defense, doing interviews is part of your job. It’s not like you sought out a reason to talk about yourself.

HAMM: Yes, there’s that. But it’s hard to escape that we live in a world where everybody is clamoring for attention, who think their life doesn’t matter if they’re not on TV or the paparazzi isn’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 is all just contributing to a vast echo chamber that serves basically to turn everything into noise. Eventually your life is lived in sound bytes and reality shows and 140 characters, becoming smaller and smaller without any nuance or deeper reflective quality. I do try to go away from that, and listen more than I talk, except of course in this situation.

PLAYBOY: Do you have the emotional stoicism of Don Draper, or are you a heart-on-your-sleeve kinda guy? Will you cry at a sad movie?

HAMM: 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.

PLAYBOY: Because it relates to your own life?

HAMM: Oh yeah, sure, absolutely. I mean come on, I’m not made of stone.

PLAYBOY: Your mother died when you were ten years old. You were so young, did you even realize what was happening?

HAMM: There’s not much. When you’re ten you’re kind of cognizant of how the world works, but it’s through the filter of a child. There’s definitely not a 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.

PLAYBOY: She died of cancer?

HAMM: Very advanced abdominal cancer. It started in her colon and then rapidly spread, like cancer does. This was in the late 70s, early 80s, 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 progressed. As such, it was a very 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 in her prime essentially.

PLAYBOY: Do you remember anything about her last days, or was it just a blur?

HAMM: 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 like, “What’s happening? What’s going on?” Just recently, the father of a very close friend of ours passed away suddenly, in a very accidental, shocking way. He had two boys, and I was like, “How are they doing?” And they were like, “They don’t really 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 that he knew that I was sad and wanted to help. He wanted to make me happy. And that’s kind of what I was like when my mom died. I was the kid who was like, “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.

PLAYBOY: Your father passed away ten years later, when you were in college. Was that easier or worse?

HAMM: It was worse in many ways. By the time you’re twenty, you have a sense of mortality. You still think you’re bullet-proof but you do have this realization that “okay, 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’re like, “Well, somebody will take care of me. I’ll land on my feet somewhere. As long as there’s Atari, something in bound to happen.” But when you’re twenty, things are significantly different and significantly harder. I’m certainly not ranking which parent I loved more, but it was very different.

PLAYBOY: You were officially an orphan.

HAMM: Exactly, yeah. 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 I do think that everything happens. And then there are consequences. And life is dealing with those consequences.

PLAYBOY: If your parents had lived, would your life had gone in a different direction?

HAMM: One hundred percent. Absolutely.

PLAYBOY: You wouldn’t have been an actor?

HAMM: I don’t know. But I think anybody that chooses any kind of career in the arts, and I’m using that term very loosely for what I do, comes from a place of being a little bit unmoored. If I grew 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 LA with no money. That sounds like the best plan.”

PLAYBOY: There was a moment during the production of Mad Men that you looked at yourself in the mirror of your dressing room, dressed in Don Draper’s suit, and realized that the character was essentially your dad. What were the similarities?

HAMM: It was the costume. There was the “ah-ha” moment of seeing myself in all that gear and realizing “I look 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. But other than that, I’m a pretty good likeness. But there was something about the suit. I remember his closet used to be filled with suits. It was like entirely suits in every style and color, like a rainbow of linen and cotton. That’s what he wore, that was his uniform.

PLAYBOY: Do you still use your dad as inspiration for Don Draper?

HAMM: 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 40s and 50s, it was all about interstate trucking, with 18-wheelers and big rigs. By the time my dad got the business in the late 60s and 70s, 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 70s and 80s and 90s. That’s what happened to the trucking industry. Container shipping became significantly cheaper and air freight was significantly cheaper. It was way easier to get stuff places, so you didn’t have to depend on trucks anymore. So my father basically inherited a business during its decline, which probably didn’t feel good.

PLAYBOY: Did you ever ask him about it?

HAMM: He died when I was 20, so I didn’t have a lot of adult conversations with him. I didn’t have the time.

PLAYBOY: Or probably the emotional maturity.

HAMM: Sure. It wasn’t what I was thinking about at seventeen. “Hey dad, tell me about your business.” I had homework to do and girls to not make out with.

PLAYBOY: If you had a chance to have a conversation with your father or your mother today, what would you ask them?

HAMM: (Long pause.) That’s an interesting question. I think about it all the time. (Another long pause.) I guess I’d just ask about their lives. The hard part of having an adult life when your parents aren’t around is just not having that adult wisdom that I think is incredibly useful as a human being. There are times, even when things are going well, that you can’t help but think that you’re some kind of giant fuck-up. But if you had a parent who could say, “Seriously? You think you’re fucked up? That’s nothing!” And then they tell you about all the mistakes and bad life decisions they’d made at your age. I think that would make a huge difference for me. I’d be like, “Oh alright, I feel better. They screwed things up so much more than I did, and they turned out okay.”

PLAYBOY: If it’d been an option, could you see yourself being the fourth generation of your family’s trucking business?

HAMM: I’m actually pretty glad that 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 almost like a standup comic, who always has to have material at the ready. I’m just not able to do it.

PLAYBOY: But you sell yourself in auditions, right?

HAMM: 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 really 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.

PLAYBOY: Didn’t you audition six times for Mad Men?

HAMM: 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.

PLAYBOY: Why didn’t he tell you?

HAMM: 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, thumbs down). If they’re powerful enough, it ends. You could have five of the greatest auditions that you’ve ever had and the sixth one you’re a little off your game or the guy had a bad piece of fish at lunch and just doesn’t like anything and it’s over.

PLAYBOY: You’ve said that you were at the bottom of their list of actors. How did you know?

HAMM: I’d been around long enough, I knew how these things worked. You go to the sign-in sheet and you see fifteen people who’ve been there before you and they’re recognizable names. At the time I remember thinking, “It’d be nice if they’d cast me but they’ll probably just cast the movie star who kind of looks like me.” It was very 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 resumes.

PLAYBOY: How’d you find out you had the job?

HAMM: 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 was like, “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 was like, “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 very pretty spring day. Matt and I had a few drinks with the network brass. And then we were riding down in the elevator, and the woman who’s 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 during the 70s and 80s. He’s a coach or manager now or something. Literally the moment they told me I got it, the elevator opened and the lobby was filled with photographers. The lights were flashing, people were rushing towards us, shouting “Oh my god, oh my god, oh my god!”

PLAYBOY: Did you think all the attention was for you?

HAMM: 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.

PLAYBOY: Your very first play was a first grade production of Winnie the Pooh.

HAMM: That’s right. I played the titular character.

PLAYBOY: Can you give us a taste? Was your Winnie goofy and bumbling, or confident and soft-spoken?

HAMM: It was more bumbling. It wasn’t really that nuanced. I was four. My mom made the costume out of a Butterick pattern and I had a pillow taped to my belly. You tumble around and try not to knock the set over. There does exist a VHS tape of this play, by the way.

PLAYBOY: It’s out there somewhere?

HAMM: Oh, I know exactly where it is. And it’s not going anywhere.

PLAYBOY: Did you have to fight for the role like you fought to play Don Draper?

HAMM: No, it was pretty easy. The teacher assigned everything, and I think I was picked to be the main guy because I was literally the only one who wasn’t terrified of standing up in front of an audience and looking like a moron. Everybody else just wanted to be trees.

PLAYBOY: In high school, you were both a jock and a theater kid, right?

HAMM: That’s right, yeah. I played football and baseball, and I also did as many plays as I could.

PLAYBOY: Those two worlds don’t often intermingle, especially in high school. Did your jock friends give you grief about doing plays, or vice-versa?

HAMM: I went to a really progressive school in St. Louis, the John Burroughs School, that was basically founded on John Dewey’s Principle of Education, which is that education is experience. You’re supposed to experience as much as you can. It was like, “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 resume.” 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 micro-analyzed.

PLAYBOY: It’s a pretty big age for self-doubt.

HAMM: Exactly, right. “What will Sarah think if I do this?” Their 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.

PLAYBOY: Were sports just a fun thing to do as well, or did you ever consider going pro?

HAMM: At a certain point you realize, or at least I realized, that you can only take athletics so far. I’m a very 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 or 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 sixty pounds and work out every day.” I was like, “Nope, not going to do that.” I was also a pretty good baseball player and had some interesting offers made to me, but they were like, “Okay, you 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 towards theater because it mixed things up. There was always another play to do, another new challenge to overcome. And the students who did theater were very much my people.

PLAYBOY: In what way?

HAMM: You go to any theater department in the country and it’s usually 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 very welcoming and not exclusionary. There’s plenty of time to be made to feel like shit once you get to Hollywood. (Laughs.)

PLAYBOY: You moved to LA in the mid-90s with just $150 in your pocket. Did you seriously think that would be enough?

HAMM: 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 LA, 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 was like “absolutely,” so I knew all I had to do was get out here. This was in an era of significantly cheaper gasoline. I drove an ‘86 Toyota Corolla which had pretty good mileage. And I had stops planned along the route where I knew friends I could stay with and get a bed and shower and free food. I went from St. Louis to Denver, where I knew a guy from college, to Carling, Nevada, where I had a friend who was a DJ, and from Carling to San Francisco, where another friend from St. Louis was staying. From there I could make it down to LA in a day and I was all good.

PLAYBOY: That must’ve been quite the trip for you to remember every leg of it fifteen years later.

HAMM: I just love road trips. I love driving and maps. This is in an era way before CDs and satellite radio, back when you could tune in to AM radio and find some weird station that you could listen to for a few hours. I loved it all. And the plan worked great, with the exception of my friend in Carling, Nevada. Turns out he moved and forgot to mention it to me. I didn’t have a cellphone, 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 LA and somehow my $150 lasted. I pulled into town on Thanksgiving day.

PLAYBOY: Just in time for dinner?

HAMM: Well, my aunt and uncle had plans elsewhere. So I actually showed up at an empty house.

PLAYBOY: That sounds vaguely depressing.

HAMM: It really wasn’t. I was just happy 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!” And then I went to an orphans’ Thanksgiving, which was hosted by a mutual friend that my aunt and I both knew from St. Louis. Coincidentally, one of the people at the orphans’ Thanksgiving was Kevin Williamson, who had just sold a script called Scary Movie, which would later become Scream. So that was my intro into LA.

PLAYBOY: And then came the hard part.

HAMM: Exactly, yeah. Then it’s time to find a job and find an agent and find a place to live and all that shit, none of which comes easily. I just called who I knew. I called Paul Rudd, who I knew from college, and said, “I’m only going to ask this 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.

PLAYBOY: Do you have any perspective in hindsight? Why couldn’t you break through?

HAMM: It was just bad timing. This was in the late 90s, when teen dramas like Dawson’s Creek were really 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.

PLAYBOY: You were too young to play the parents, but too old-looking to play the teenagers?

HAMM: Right, right. I was right in between the two camps. I remember once I went to an audition and there’s Peter Gallagher and we’re trying out for the same role. I was like, “Are you kidding me? I’m 27!” No offense meant to Peter Gallagher, but come on, man. Why am I here? It was depressing. So I got dropped by my agent, got cast in a play, got another agent, that agent got me my first 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.

PLAYBOY: Did you have a plan B, in case acting didn’t work out?

HAMM: Not really. I came to LA 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 seventeen percent of my life. In my opinion that was more than enough time to give it a legitimate shot.

PLAYBOY: Did you make your deadline?

HAMM: 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.

PLAYBOY: How did you celebrate?

HAMM: 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 really good friends. It was a pretty great birthday. I thought, “Yeah, man, This is it. This is the best of everything right here.”

PLAYBOY: Were you comfortable enough with your acting career to quit waiting tables?

HAMM: I’d quit like a year earlier. It was weirdly hard to give up.

PLAYBOY: Why? Did you still need the money?

HAMM: Not really, 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 very comfortable behind a bar and I’m very comfortable with an apron on. It doesn’t bum me out. I’m totally fine with it. There will always be restaurants and there will always be 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 disappear, clothing stores, record shops, newspapers, TV shows, everything ends up on the computer. But not restaurants. There are definitely worse day jobs to have.

PLAYBOY: What was the worst for you?

HAMM: I did set dressing on some softcore porn films. That was hands-down the worst. I was working from seven to seven on the crew and it was horribly depressing.

PLAYBOY: Set dressing as in the props?

HAMM: 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 had to be there in another. I’m sure there are more terrible day jobs in LA, but it’s definitely on the lower end of the spectrum on the wonder of movie-making. 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.

PLAYBOY: Your social life at the time consisted of going to comedy clubs and befriending comedians. How’d you end up in that world?

HAMM: There’s a nightclub in LA called Largo, and Mondays at Largo were the hottest night in town for comedy, or at least for the particular brand of comedy that I really liked. It was kind of an underground, hipster comedy scene, with people like Sarah Silverman and Paul F. Tompkins and Patton Oswalt. And it was five dollars to get in. It was cheaper than the nightclubs, which I hated anyway. The drinks at the LA 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 just by hanging around all the time.

PLAYBOY: You became good friends with many of the performers, like Zach Galifianakis?

HAMM: Yeah, I know all those guys. It’s weird, everybody in that social circle kind of 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 I’m like, “This thing happened to you.” And he just smiles back at me and he’s like, “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.

PLAYBOY: What’s it like socializing with comics? Are they shy and reserved, or is it a nonstop barrage of jokes?

HAMM: All of the above. And if it’s the latter, I generally don’t participate. I’ve 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.

PLAYBOY: But you can hold you own with comics. You were hilarious on 30 Rock.

HAMM: 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.

PLAYBOY: You’re being humble. What about that sex scene with Kristen Wiig in Bridesmaids? You definitely weren’t just keeping a straight face there.

HAMM: No, I guess not. (Laughs.)

PLAYBOY: When you’re saying things in a sex scene like “spread my cheeks” and “make monkey noises,” is that awkward? Do you feel embarrassed, or are you too caught up in the moment?

HAMM: It’s like running in the rain. There’s a certain point where 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 in 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 6’2”. 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 just sort of melts away and you’re like, “Alright, 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.

PLAYBOY: It probably helps that this wasn’t Wiig’s first over-the-top sex scene in a movie.

HAMM: That is a thousand percent true. Look at something like MacGruber. It just speaks to the fact that she is utterly fearless and has no qualms about making herself look ugly or ridiculous for a joke. If I’ve learned anything from working with comedians, it’s that shame is counterproductive. It’s such a waste of time to be stuck thinking, “Oh, my ass looks fat,” or “my belly isn’t sucked in enough.” The best comics are so present and so in the moment and ready to do anything. Shame or self-consciousness never enters the equation. It’s just, “Alright, let’s do this.”

PLAYBOY: Do you follow that same instinct as an actor? Are you willing to do anything?

HAMM: Oh yeah, sure. I’ve been that way since the first grade, when I got the Winnie the Pooh role. I had no problem saying, “I’ll talk loud! I’ll wear the bear suit!” It’s not just about comedy. All acting, at least all good acting, is a willingness to look like the fool.

PLAYBOY: After Mad Men ends, will you focus more on comedy or drama? Or does it matter?

HAMM: 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 very fortunate in that I have not worked with many douchebags. 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.

PLAYBOY: It probably helps when you collaborate with people like your girlfriend.

HAMM: Yeah, I already know she’s none of those things. She’s the least narcissistic, mean-spirited person I know.

PLAYBOY: You and Westfeldt have a new movie coming out soon, Friends With Kids.

HAMM: That’s right.

PLAYBOY: When you don’t have children and you make a movie about the fear of having children, it practically begs to be read into.

HAMM: (Laughs.) Oh yeah, 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, “maybe you shouldn’t have had kids.”

PLAYBOY: Because it’s a bigger responsibility than they’re ready for?

HAMM: That’s what it seems like. Maybe they should’ve waited. But of course if you wait until you’re ready to have kids than 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.

PLAYBOY: Is it safe to assume you don’t want children?

HAMM: I don’t have the driving force to have a baby. But 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 one of us has that pull. I don’t know, it could happen tomorrow, I have no clue.

PLAYBOY: It’s admittedly an unfair question. Nobody gets asked things like, “Why did you decide to have kids?”

HAMM: Right, right. It’s always “Why didn’t you?” I’m very zen about it and I hope Jen is too. We talk about it enough, I’m pretty sure I know where she stands. It’s hard because it becomes a story when it’s a pretty personal and private thing. I will say that I like other people’s kids a lot. I’ve been a teacher, and I’ve taught 8th grade through 11th grade, and I’ve done daycare. The reason I like other people’s kids is because you can do this. (Mimes handing the baby back.)

PLAYBOY: When you were working in daycare, did you see something that scared you? Something that made you think, “Nope, not for me?”

HAMM: Oh sure, every day. But I saw a lot that I loved. Kids at that age are just little bundles of energy. It would sort of energize me. And I think it was unique for them, because in daycare settings in general, there aren’t a lot of masculine male figures. There just aren’t. They’re mostly women. I think it’s something like a 90/10 women-to-men ratio. When I was growing up, I didn’t have my first male teacher until junior high. That’s 13 years of being educated entirely by women. I guess because teaching is considered a feminine profession or something, which is bullshit.

PLAYBOY: What about marriage? Have either you or Westfeldt actually said “let’s not get married?” Or is it a mutual understanding?

HAMM: It was never really a discussion. I think marriage very 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 really 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 go, “Oh yeah, that’s it! That’s what I want!”

PLAYBOY: 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?

HAMM: 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.

PLAYBOY: Draper took his identity from a dead solider in North Korea. If you could do the same thing and become somebody else, take their name and identity and start over, who would it be?

HAMM: (Long pause.) 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 forty years now, and I’m getting kind of used to it.

(This story originally appeared, in a slightly different form, in the April 2012 issue of Playboy.)