This story appears in the September 2016 issue of Playboy. Subscribe

If he wanted to, Andy Samberg could still be ruling viral video with shorts like Dick in a Box, that indelible ode to the joys of gift wrapping your junk and presenting it to your lover. After Saturday Night Live lobbed that comedy grenade, co-written by Samberg and recorded with Justin Timberlake, it hit 28 million views in less than a year. Later cited by Billboard as one of “the most iconic musical moments in the show’s history,” it copped an Emmy and inspired two sequels, to say nothing of the countless fan reworkings.

Samberg chased that one with other huge SNL digital shorts, including “Jizz in My Pants,” a New Wave banger about premature ejaculation that to date has more than 153 million views; “I’m on a Boat,” the Grammy-nominated nautical rap featuring T-Pain; and “I Just Had Sex,” featuring Akon. All these Samberg created with SNL writers Jorma Taccone and Akiva Schaffer, Samberg’s buds since junior high and inseparable creative partners.

Instead of settling into a career as a younger hybrid of “Weird Al” Yankovic and Adam Sandler, Samberg has pivoted toward a sunnier, more middle-of-the-road and—dare we admit it?—more family-friendly audience. He left his seven-season SNL stint in 2012 and played Sandler’s long-lost son in the movie That’s My Boy, letting the star handle most of the cruder, more desperate jokes. He spent nearly two years playing a New Age slacker on the BBC Three sitcom Cuckoo. He even went G-rated, voicing characters in the Cloudy With a Chance of Meatballs movies, a pair of Hotel Transylvania entries—forerunners to the upcoming Hotel Transylvania 3—and Storks, out this month. He won a 2014 Golden Globe for his performance as a man-child detective on Brooklyn Nine-Nine, the fourth season of which kicks off this month. He performed at last year’s Oscars and hosted the 2015 Emmy Awards. He also co-wrote, co-produced and starred (as a drop-crotched and distinctly Bieberesque entertainer) in this summer’s warmhearted satire Popstar: Never Stop Never Stopping. Oh, and in 2013 he married his longtime girlfriend, singer-songwriter-harpist-actress Joanna Newsom, with whom he handpicked and restored the furnishings for their 1920s mansion. Smart moves, all of them, for a baby-faced comedian bearing down on 40.

Andrew David Samberg was born in Berkeley, California on August 18, 1978. His mother recently retired from teaching special-needs elementary school students; his father is a photographer. Far from the most attentive student at Willard Junior High, where he met Taccone and Schaffer, Samberg dedicated himself to cracking up his classmates, soaking up the comedy chops of various Saturday Night Live casts and watching classic comedies on TV. After high school, he spent two years at the University of California, Santa Cruz before switching to New York University’s Tisch School of the Arts, from which he graduated in 2000. He reunited in Berkeley with Schaffer and Taccone, and the trio moved to Los Angeles—into an apartment they dubbed the Lonely Island, which became the namesake of their collective comedy endeavors. Their early video work led to Samberg landing an agent, auditioning for SNL and joining the cast in 2005, with Schaffer and Taccone signing on as writers. That first year, their “Lazy Sunday” digital short marked the first time millions of people uttered the term viral video. Since then, they’ve released four albums, partnered on a few movies and generally made friends with every celebrity you can name. Without sacrificing his relatable dorkiness, Samberg has set out for full-spectrum comedy penetration on a worldwide scale.

Contributing Editor Stephen Rebello, who spoke with Don Cheadle for the April Playboy Interview, spent a recent afternoon with Samberg in West Hollywood. “Don’t be fooled by Andy Samberg’s knack for playing smug goofballs,” says Rebello, “because here’s a guy who’s surprisingly thoughtful and canny. Whether he’s talking about his past, his career, his tastes or his goals, he’s smart and sincere and unafraid to come across that way. He knows exactly what’s up and where he’s headed. Frankly, I didn’t see it coming. But what a relief.”

You’re best known for being an SNL cast member, making viral videos and hosting awards shows. What made you want to saddle up for a workplace sitcom like Brooklyn Nine-Nine?
People who know my actual personality know I’m not walking around rapping about dicks all the time. That’s just one part of who I am, and it happens to be the most popular part. Doing Brooklyn Nine-Nine changed a lot of people’s opinion of me. They were able to see the humanized me, for which I’m grateful. Michael Schur created both Brooklyn Nine-Nine and Parks and Recreation, and there’s such sweetness to both shows. By the nature of the characters’ profession and the locale, Brooklyn is a slightly tougher, more cynical universe than Parks, but it’s an equally heartfelt universe.

Was the role of Detective Jake Peralta—wisecracking, highly competent, immature, emotionally stunted, upbeat—written for you?
There was no script when they pitched me the kernel of the idea and asked me if I wanted to do it. From the point I said yes, they wrote toward me. I knew Amy Poehler, of course, from working with her on SNL, so I talked with her about her experience with Parks. I had also done a guest acting role on Parks, and it was so fun, so comfortable. It just felt like a good life.

What’s up with your character this season?
Jake and Captain Ray Holt [Andre Braugher] are in Florida in witness protection. So we have new stuff to play with and I’m really excited. It’s one of those rare work experiences where I work on a show I adore, everybody gets along, and I love everyone I work with. I’ve been lucky so far with this one and the fact that, by all accounts, I was on SNL during one of its least dysfunctional times ever.

You grew up in Berkeley in the 1990s. If you made a music video of your experiences in northern California back then, what would be the vibe, the sound and the look of it?
The sound would be a lot of early-1990s hip-hop, R&B, reggae, dancehall and a heavy Latino influence. The look would be Cross Colours and Girbaud jeans, and the smell would be Drakkar Noir—or Preferred Stock if you couldn’t afford Drakkar. All that mixed with a vibe of the civil rights movement and original 1960s-era hippies. It was a fascinating and wonderful place to grow up, definitely the melting pot people say it is.

How is Berkeley not like what people say it is?
Berkeley is less hippie and touchy-feely than people think it is. That was the 1960s. The version I grew up in was much more “city,” although when I was a kid there were still lots of walkouts and protests. You were living in a world that was more politically charged just by the nature of the city’s history. It’s almost expected.

As a kid, how did you navigate those social, political and pop-culture currents?
By being into a lot of different stuff. I would describe myself as not cool but not unpopular. I played soccer, so I knew a lot of people who were athletic. I listened to reggae and smoked weed sometimes, so I would hang out in the park, play Hacky Sack and go with friends to Reggae on the River. I was into classic rock like Floyd and Zeppelin, so I’d hang with those dudes. I was really deep into hip-hop, so I would hang out with those dudes and with the graffiti dudes and the skater dudes.

Did those dude groups intersect?
The Venn diagram had a big intersection, and that is the beauty of growing up in Berkeley. Kids there were the way I see a lot of young people now—I say “young people” like I’m super old, but they’re young to me. It was one of those places that was slightly ahead of the curve of the internet. Now, with the internet, a lot of kids are into a ton of different stuff. But culturally, socially, musically, my friends and I were already that way in the 1990s, when kids in other parts of the country may have been a little more factionalized in their interests.

What were the advantages and disadvantages of being the youngest kid in your family, and the only boy, with two older sisters?
I was a textbook youngest child. I got a lot of positive attention. I had an easy ride. I don’t try to paint it any other way. I saw my sisters go through their trials and learned by watching their experiences. By the time I was going through my teen years, my parents were more mellow. I never got into trouble that much.

Define “that much.”
Like drinking with buddies, passing out at a friend’s house, getting home and my parents being like, “Where the fuck were you? We were worried.” But I never got caught stealing or cheating. I kind of cruised. I had a very enjoyable time growing up. I was always sort of the tension-breaker. Not that there was a ton of tension in my family, but I was the goofy one who was always being sarcastic, joking around and trying to lighten the mood.

Your mother and father had nothing to do with show business.
My mom just retired from teaching elementary school, primarily in the special-needs program because she’s fluent in sign language and is partly hard of hearing herself. She uses hearing aids.

Was she born with a hearing problem?
It didn’t begin until, I believe, she was in her 40s. But long before that she had learned sign language. She just was drawn to it and followed that instinct. She feels she subconsciously somehow just knew, which is so strange and interesting. If it were anyone else saying that, I’d be like, “Yeah, right.” But I’m inclined to believe her. She has strong, clear instincts. That’s kind of her deal. She’s the best.

Your father, who is a professional photographer, is also very talented. His photos—of kids smoking weed, guys with painted faces tripping out and hippies and their “mamas” leaning against their motorcycles—look found rather than staged. It’s the kind of thing that period movies almost never get right.
When people nail a period in film and television, it’s immensely satisfying. I think the TV series The Americans gets the 1980s right. I thought David Fincher did a really nice job with the 1960s and 1970s in Zodiac. For that same reason the first Alien somehow feels honest about the future: It’s not saying, “Hey, look at all of this futuristic stuff.” The stuff is all just there, and it’s used stuff. For me, the silent minutes at the beginning of Alien is one of the best sequences in film history. I loved Prometheus too, and it looked fucking amazing. So few people go as far as the level of detail that Ridley Scott and everyone else put into it. I’m big into sci-fi movies and novels, always have been.

Your dad has shot incredibly striking nudes. As a kid, did you secretly rifle though his files?
When he started doing that kind of work, I was in high school, so I was more mature about it. It was definitely a slightly strange moment to understand that my dad, who’s married to my mom, goes to work and takes photographs of naked women. But then you see the photos and you think, Oh, it’s very much about art and doesn’t feel voyeuristic. And my mom didn’t seem to care. They had a good thing going.

How much were girls a part of your life growing up?
I was always a relationship guy. In college and right after college, I was in a couple of long-term relationships. I didn’t play around. That’s the influence of having two older sisters.

You didn’t wait until college to lose your virginity, though, did you?
I was, I believe, 16 or 17. It was at summer camp. I was on the junior staff and she was girls’ head counselor. She was 24. She could tell I probably was a virgin. I was flirty; there was a friendship and a playful thing between us, but I didn’t really think it would ever be real because of the age difference. I think she just decided for me. It was only once. I wouldn’t say I was good, but it was great for me.

Our generation wasn’t doing anything but wearing super-baggy clothes and condoms all over. We were the D.A.R.E. generation, the scared generation.

Were your parents cool about sex?
My folks, my mom especially, were hippies from New York who moved to the Bay Area in the summer of 1970 or 1971. We had this cartoony book that we’d flip through, with illustrations of a sort of doughy-looking couple having sex and text explaining where babies come from and all that. There was not a ton of talk about it. But my teen years were in the 1990s, and there was so much talk about safe sex because of AIDS. My friends and I joke a lot about how the generation before us was all coked-up and fucking, the generation after us was all on ecstasy and fucking, and our generation wasn’t doing anything but wearing super-baggy clothes and condoms all over. We were the D.A.R.E. generation, the scared generation.

Growing up, did you have sexual fantasies about any celebrities?
I was enamored of Cyndi Lauper, just obsessed, when I was a kid. I’ve never met her, but I’m friendly with Paul Reubens, who’s friendly with her. I’ve gushed to him about how much I love her. She’s incredible. I still listen to her first record, She’s So Unusual, all the time. It’s a perfect album, and not just the cuts that were hits.

You said that you had a lot of friends in different groups. Is it an unwarranted cliché that all comedians were loners as kids?
I can be on my own for hours, but I much prefer to be around people. When Akiva, Jorma and I were working at SNL, the walk to the restroom was long. I would always ask people if they wanted to come with me because I didn’t want to be lonely on the walk.

Would they humor you?
Sometimes. And if they weren’t ready, I’d wait them out.

Do you remember the first time you got a laugh? There’s a 1986 video floating around of you as a third-grader, when you played Daddy Warbucks in Annie. Backstage you were already bouncing up and down and pretty much going, “Look at me!”
I don’t remember my first laugh, but I know that making people laugh was my way in. It was just what I was good at early on, and I went with it. Like a lot of people say, “Oh, I developed a sense of humor to traverse the world socially”—which is a word I definitely use, traverse.

It doesn’t sound as though you needed it the way others do.
I just loved it. I loved it immediately. Even when I was really little, I found Garfield books in the library, and I was like, “There are jokes in this and I’m going to consume and interpret this.” I was six or seven and wanted to get The Far Side calendars or the comedy catalogs where you can order whoopee cushions and the most base comedy stuff. And very early I started watching SNL, Mel Brooks movies and Monty Python. I was drawn to it. I knew that’s what I loved. SNL was my dream from the time I was eight.

Video shorts were what put you on the map and helped you realize your dream of getting on SNL. When did you first pick up a camera and start making stuff?
Willard Junior High and Berkeley High School were the first times I recall shooting things where I was hoping to be funny. My family got a home video camera around 1988, and a friend and I started shooting “sketches.” Even before that, in elementary school, my friends and I took a boom box with a cassette, a mike and a “record” option and we would do crappy little-kid versions of radio plays and stuff like that. I met Akiva and Jorma at Willard, and much later I went to the University of California, Santa Cruz, where Akiva was majoring in film. But I transferred my junior year of college to study film in New York at the Tisch School of the Arts. Since 1988 until probably today, all I’ve really done is try to put comedy on film or video.

After college, when and how did you, Akiva and Jorma reconnect?
That first summer after we all graduated, we showed each other all the stuff we’d been making. We clearly wanted to do the same thing and we were already friends, so why not band together? Strength in numbers, as the Golden State Warriors would say—until they got beat. Heartbreaking. Yeah, I’m a huge fan. Anyway, we debated staying in our parents’ basements, trying to shoot stuff in Berkeley and maybe putting together a website.

In the end, you opted to share an apartment in Los Angeles.
That apartment was the original Lonely Island. That’s what we named it. Having just lived in a one-bedroom apartment in New York with my buddy [writer-director] Chester Tam and a lot of mice, this place on Olympic Boulevard felt big. We turned the dining room into a fourth bedroom, put up a partition and crammed four dudes into that apartment. Even so, it was pretty big. I mean, we set up our original Nintendo and I remember thinking, Wow, L.A. is very comfortable. We hung out, shot stuff, started writing and worked odd jobs.

How odd?
I worked a couple of temp jobs and got fired from one because I was late, which is still a problem for me. My first actual job was working the graveyard shift in the vault of a color-correction company. They’d plop down 50 reels of film in boxes and I’d enter them 100 percent accurately into this antiquated and complicated system. It was mind-numbing, but the people I worked with were very nice. That same year, my dad suggested that if I went to grad school, maybe I could become a film professor. I remember using it as motivation. He was just being sweet, but I was like, “How could you give up on me?” I also continued to do stand-up, which I’d started doing my junior year of college in New York. I did that for the next five years in L.A., before we got hired on SNL.

What did you learn from doing stand-up?
A lot of comedians do open-mike nights as a badge of honor. I didn’t get much out of that. It was more useful to do “bringer shows,” where you harangue three to five people to pay too much money to come see you. In that setting, I was able to much better gauge whether my stuff was working with real people and not just comics. I read Harpo Marx’s autobiography, and it was so eye-opening to learn how the Marx brothers would tour their shows across the country, then wind up in L.A. and shoot the movie version in, like, three takes. Incredible. They’d rewrite on the fly and do their live shows over and over, knowing for a fact which jokes worked everywhere. Now you do it in reverse order: have a test screening, see what works and then go shoot more.

And you and your two buds continued to make shorts?
There is a monthly event-network-website thing called Channel 101, started by Dan Harmon, who went on to create Community, and Rob Schrab, who later co-created The Sarah Silverman Program. They screen a bunch of fake TV shows of five minutes or less. A live audience votes and the top “shows” get “renewed,” meaning you make another episode and just keep going until you’re eliminated. It started as an exercise for them and their friends, then it got more traction and they started to get submissions from all over. We created a few shows for it, the most successful of which was The ’Bu, a deadpan spoof of The O.C. I love that Zucker brothers style of dry comedy. That’s where we met Jack Black and Steve Agee and lots of really cool people in comedy.

You were asked to write your first MTV Movie Awards, with Akiva and Jorma, in 2004. Was that an offshoot of Channel 101?
Murray Miller is a writer on Girls, and he and I created the HBO tennis comedy 7 Days in Hell. He’s an old friend from summer camp who convinced me to apply to NYU because he went there before me and then convinced me it was a good idea to move to L.A. He and I even did stand-up together for the first time. His brother helped me get a job as a runner for National Geographic Channel, and then Murray helped me get my next job, as a writer’s personal assistant on Spin City. He helped us get hired as writers on the MTV Movie Awards. We made $300 or $400 a week split three ways after taxes, but you meet people. There are folks we’re still in touch with because of that job. And it led to SNL.

How does Jimmy Fallon come into your story?
Jimmy was the host for the second year we wrote for the MTV Movie Awards, and he brought a ton of the SNL folks with him, including Liz Cackowski, who came to help write for the awards show. We hit it off with Jimmy and his buddies—in fact, Akiva is married to Liz. Like with Harmon and Schrab with Channel 101, we were in the company of like-minded people. There was a crackle to it. You could tell you were at the center of what was happening.

I took off my pants to reveal these crazy-tight shorts. Lorne Michaels says that was the moment he decided to hire me.

When you auditioned for Saturday Night Live, did you plan to drop trou?
Two or three days after my first audition, I was told they wanted to see me again and that I didn’t have to do a totally new audition. Then, a couple of days before the second audition, I got tipped off not to do the same audition. I don’t know whether it was a mix-up or a head game, but I went to the flea market and bought this ridiculous pair of supershort Adidas 1980s jogging shorts. I was hanging out with Liz, who already worked at SNL, so I showed her the shorts and we came up with this bit about an out-of-breath jogger making random references to events from 1982. It made us laugh, so for the audition I put the shorts on underneath my pants, and in the last part of my audition, I took off my pants to reveal these crazy-tight shorts. Lorne Michaels says that was the moment he decided to hire me.

Ken Jeong, Jason Segel and Sacha Baron Cohen have gone full monty in movie comedies. Will you up the ante?
I don’t think I’d ever do it, because of the internet. Once you show your dick, that’s the first image that comes up on Google for the rest of your life. I don’t want my dick on the internet.

Apparently Lorne Michaels isn’t a fan of SNL cast members cracking up during sketches for the sake of breaking or trying to make a sketch work. Will you cop to ever doing that?
To get laughs? No. But I genuinely lost it twice. One time was during the Kenan Thompson “Scared Straight” sketch, where he’s an ex-con trying to scare a bunch of teens who got into trouble for underage drinking. Kenan got in our faces and acted insane. Bill Hader broke first. We’re good friends, and it’s really hard not to laugh when your friend’s laughing. Besides, it was funny. The other time was when Will Forte was doing a stupid halftime dance with Peyton Manning to the theme from the 1960s Casino Royale movie. I think there were seven of us in the scene. Again, I believe Bill was the first to go, but in my defense, everyone lost it. Fred Armisen lost it and so did Kenan, which rarely happens. We all went down at Will doing that stupid dance.

You got hired as an SNL cast member, and your Lonely Island partners were hired as writers. Did the pressure of doing the show put a strain on your relationship?
I had done a lot of stand-up and we led with me for that first audition. Akiva didn’t want to be on camera. He took a writer’s meeting. Jorma auditioned, but he was a theater major. He is super funny and would have been great on the show, but he never did the Groundlings or tried improv or anything like that. We all wrote and submitted a writers’ packet together, and Jorma and Akiva helped me write my audition. The fact that we all got hired was incredible and a victory for the three of us. Once we were hired, we started to make those videos together, and it was always about the three of us. The nature of the show sometimes threatened to drive a stake between us, but we rarely let it happen.

Did you accomplish all you set out to do on SNL?
We far exceeded my expectations. The 40th-anniversary special last year was a mind-blowing and eye-opening experience for us. There was a long section where a majority of the clips were things we had worked on. We looked at each other like, “Holy shit, we’re being treated like we’re really a part of this show.” We’re obviously very close with the cast that was there at the time—Bill Hader, Fred Armisen, Amy Poehler, Maya Rudolph, Kristen Wiig—and we all talk about how when you see yourself in clips sandwiched between Chris Farley, Gilda Radner, Bill Murray, that whole long list, you don’t allow yourself to believe you belong among them. But it’s nice to think that anyone watching the show thinks that.

When did you first feel “I’m famous”?
You get hired on SNL, but except for the show’s die-hard fans, nobody knows who you are until you do something that everyone’s talking about. After we did Lazy Sunday with Chris Parnell in 2005, I would be out in public and people would go, “Hey, Lazy Sunday!” That first wave feels the biggest because you’re going from not at all famous to thinking, Holy shit, somebody just spotted me on the street. It’s both exhilarating and terrifying, but the truth is, you’ve just scraped the surface to the point that, if there’s a Google search for you, now at least there’s something there. The second big one was Dick in a Box, and to this day that’s still probably the biggest. Lorne likes to joke about the thing you’ll be most remembered for on your tombstone. He’s like, “I’ll be Lorne ‘SNL’ Michaels, and you’ll be Andy ‘Dick in a Box’ Samberg.” I’m very comfortable with that. I love that video. I still find it really funny, and it was huge for our careers. It was a moment. There was a Justin Timberlake explosion happening and the video got picked up everywhere. That was the first time I really felt the power of the media and the first time I was getting more attention than I was comfortable with.

Did it ever get creepy?
Knock on wood, but I’ve been pretty lucky in that what we make generally appeals to the types of folks we’d like to be interacting with. It’s people who are really into comedy and have been since their childhoods and teen years, and it’s sort of the fabric of their social lives. That’s incredibly gratifying. Like when a group of teenagers comes up and goes, “We quote your stuff all the time,” that’s the ultimate compliment because that was basically our religion coming up.

There is, of course, that other comedy cliché—that all comedians are depressed. Have you ever had to dip into the Xanax or talk to a therapist?
Yeah, I have. Not a ton. I’m generally a pretty happy person. For a lot of people, the honesty and realness that produce the best comedy means you’re facing the world as it is. You’re trying to uncover some truth, and that can be painful and scary. There’s a lot of things about being a human on earth that there are no answers to, and that’s the scariest part of it, depending on your faith and what you believe. I think most comedians believe in comedy, which we do with some pretty daunting unanswered questions, and that can lead to depression. That said, when I get down it’s generally more about working myself too hard and losing my handle. Or something incredibly sad happens in the world or in my world and I’m affected by that. I definitely feel things deeply. And when you feel great joy and major highs, you are susceptible to major lows.

I had this moment of clarity about online comments: None of it matters. All of it is easily ignored.

Do you check out what people on the internet say about you?
In my third or fourth year at SNL, I made the mistake of looking. There was some awful shit, things that made me think, You’re the only one everyone hates. I read one that basically said, “He should fucking kill himself so he can’t procreate.” That was so harsh that I actually found it funny. As an experiment, I looked up people who were at the height of their game, people whose achievements I aspired to, like Will Ferrell, Jack Black, Amy Poehler, Tina Fey, Jim Carrey. They all had the most horrendous shit written about them. And I remember reading people say how much they hated Will Ferrell and how he wasn’t funny, knowing in my heart that he is likely the funniest human being on planet Earth and can do no wrong. That’s when I had this moment of clarity about online comments: None of it matters. All of it is easily ignored. That’s helped tremendously.

Do you ever miss your anonymity?
That can be managed too. There are folks who do it, my wife, Joanna, being one of them.

Your wife, Joanna Newsom, creates music that is so uncommon and introspective that she draws comparisons to artists like Joni Mitchell and Kate Bush. Were people surprised when you first got together, let alone when you got hitched in 2013?
At first a lot of folks who were fans of hers found it confusing that we were together, which I totally understand. When you care about someone’s art that much, you have a relationship with it. Her work is so personal, special and emotional. She’s one of the greatest songwriters ever. If someone I admire artistically starts dating someone I don’t find worthy of their art and gifts, I’ll allow it to bum me out.

Were you a fan before you met?
Oh yeah. I listened to her second record, Ys, every day for almost a year. That was my second year on SNL, so it was around 2006, 2007. I would wake up to it, listen to it on my headphones in the subway and then listen to it in my office.

Was it awkward meeting her at one of her concerts?
I figured it would just be me sort of bowing and saying my pleasantries, but she’s into comedy and is really funny. She was a great fan of Dick in a Box and Lazy Sunday, and she, her brother and sister had watched all our weird early Lonely Island stuff. We became friends very quickly, but it wasn’t like either of us was pursuing the other. I think when we met she was in another relationship. We kept in touch for a while, and then eventually the timing was such that we found ourselves saying, “Hey, we’ve been friends. What’s going on?” We’ve been married three years this month.

If the two of you were to have children or adopt children, what aspects of yourself would you hope they wouldn’t inherit?
Impatience. It’s something I grapple with. I can get very flustered by deadlines. I get asked a lot why Akiva and Jorma direct and I don’t. My answer is that I really don’t want to because I’m not good at multitasking. I get overwhelmed very quickly. I like to focus on one thing at a time and give it all my attention. But kids—I hope they laugh a lot.

Do you feel that marriage has changed you?
Just being in that relationship made me happier, calmer, more comfortable with life. Like I said, I don’t really love being alone, but the idea that you get to spend a good chunk of time with someone you’d rather be with more than anyone else? Incredible. We love going to nice dinners, but we also like staying home and watching Game of Thrones, Chef’s Table or the DVD extras for Alien.

As TV watchers, have you ever bought something because you saw it on a TV commercial?
I got a Squatty Potty.

You did not.
I did. The commercial sold me. I don’t know if it was the prince, the unicorn or whatever, but I was like, “I’ll buy it and try it.” It works fine, but it’s less comfortable. Also, I’m not trying to speed up that time in my life. On the toilet and in the shower are the two places I get to truly be alone and think.

Do you have any fears that other people tell you are irrational?
Not that people tell me are irrational, just your basic fear of death or fear that I won’t be able to work anymore. Also, fear that I’ll be in a plane going down. The best death you can hope for is a peaceful passing surrounded by loved ones. The idea of being ripped from a plane in the air just feels so helpless and terrifying. This is getting dark.

It depends on your view of the afterlife, right?
My suspicion is that it’s like Jon Snow says: “Nothing, there was nothing at all.” I believe in energies and that there’s probably some transfer into the universe of whatever it is that makes you alive. But I don’t believe in the retaining of your consciousness.

How did you react when the Lonely Island’s recent music mockumentary, Popstar: Never Stop Never Stopping, got more love from critics than from ticket buyers?
It would have been nice if it had made us all a lot more money. We probably would have been given carte blanche to make another movie. But I also feel that if we wanted to make another movie, we could. There are so many outlets now. I’m not complaining about how much money I have. I’m fine. When we put out Hot Rod in 2007, it didn’t perform the way we wanted, but during a college tour promoting Popstar, kids showed up dressed in Hot Rod costumes and with Hot Rod posters and DVDs. It found its audience. We wanted to make a movie that people would talk about in the same sentence as Billy Madison or Wet Hot American Summer. We’re really happy with how Popstar turned out.

When you were coming up, you were often compared with and said to resemble Adam Sandler, with whom you made the raunchy That’s My Boy. Do you envision yourself emulating his career moves?
One of my favorite things Sandler ever did was Punch-Drunk Love. I know the director, Paul Thomas Anderson, a little, and I know a lot of people were surprised when that casting was announced. It’s fucking great, a perfect movie, and Sandler is great in it—vulnerable, believable, funny and heartbreaking. Put your trust in an incredible filmmaker and it can work out great. Everyone who has ever been in front of a camera wants to get a call from Martin Scorsese, Steven Spielberg, David Fincher, Paul Thomas Anderson, Spike Jonze, Wes Anderson—from one of the many incredible directors you can trust.

Have you ever been called by one of those directors?
The last time I really auditioned for anything was while I was at SNL. It was a one-line thing for the Coen brothers—incredible—for Burn After Reading. I came in, said my line once, and they were like [in a monotone], “Okay.” I was like, “Oh boy.”

So what’s next on the agenda?
This is the most relaxed I’ve been in years, as the half beard would imply. I’m very happy. I’ve been sleeping a ton. I’m regenerating, going on family trips.

Besides the new season of Brooklyn Nine-Nine, what’s next for you and the Lonely Island?
I did a few scenes playing Josh Peck’s mean older brother in a movie for Netflix called S.B. Bound, directed by my old NYU roommate Chester Tam. I’m basically like Bill Paxton’s character Chet from Weird Science. We’re producing a very odd and funny movie, Brigsby Bear, starring the brilliant, wonderful Kyle Mooney. The tennis comedy we did last year with Kit Harington for HBO, 7 Days in Hell, was fucking nuts, and we’re now doing one around the Tour de France.

What’s your comedy philosophy?
Go after whatever’s funny at the moment. When you have a winner, nail it and keep nailing it. I met Mel Brooks at the party after the 2015 Emmys, which I hosted. That was a “holy shit” moment. Mel Brooks said, “You were great because some of the jokes you told were great and some of them were shit, but you told the ones that were shit like they were great.” The other people in his circle and I laughed really hard. He and I sat down and I told him how much he meant to me, how I grew up watching his stuff and blah, blah, blah. I saw Nick Kroll and John Mulaney, so I called them over and he introduced himself to them. He goes, “He was great tonight, wasn’t he? Some of the jokes he told were great and some of them were shit, but he told the ones that were shit like they were great.” It was so old-school and beautiful, where he was like, “Yeah, I told a joke and it got a huge laugh, so I’m sticking with it.” His inflections were identical. He knew he had a winner, so he just nailed it.

Sounds like life is good at the top for Andy Samberg.
Comedy is such a strange thing in the world. On occasion, it can be treated with a lot of reverence, but it’s generally treated a little bit less than reverentially. Still, I’m doing this for a living. People call and ask me to come do comedy. I’m writing comedy, and people are letting me make it. I’ve already won. Everything from this point on is about what I want my career to look like. When it’s over, I want to stand by all the things I’ve made.