One of the big questions posed by Palm Springs, Andy Samberg’s new wedding-goes-Groundhog Day romantic comedy, is also a timely thought experiment: If you had to spend the rest of eternity stuck in a single day with a single other person, would that be hell? Or, if you were lucky enough to be stuck there with the right person, might desert-oasis purgatory in fact be a kind of heaven? The film picks up after Samberg’s Nyles has re-lived the same hipstery Palm Springs wedding a million times, and right before he drags Cristin Milioti’s sister of the bride into his infinitely recurring marital nightmare. Together, and with more than a few Lonely Island-style hijinks, they try to escape their time-loop. Along the way, they consider the horror—or is it joy?—of eternal cohabitation.
For better or worse, the circumstances of quarantine have led couples everywhere to confront a similar question: what happens to a relationship when every day is the same? Samberg, joyfully boyish at 41 in ballcap and Studio Ghibli tee, opens the first of our two Zoom calls with an admission. “It's weird to be doing press again at all,” he says, “thinking about saying anything about the world other than COVID or the protests and everything, and George Floyd.” This wasn’t an idle gripe. Brooklyn Nine-Nine, his sitcom about an affable band of detectives, had been pulled into the national debate around policing sparked by Floyd’s death, as audiences and networks alike began to rethink the merits of shows about benevolent cops. But Samberg had Palm Springs to promote, as both star and producer, and had brought himself around on the idea. “You know, the world was kind of fucked up before, and it's still fucked up, and we were doing press before, and making movies,” he says. “I'm going through all the same stuff,” he’d realized, “and at night I want to watch stuff. So I guess putting something out is okay.” What he’s putting out has that newly relevant pandemic layer, its echo of our endlessly repeating days. And Samberg makes no secret of the fact that he’s plenty happy for this to be the recurring day he’s stuck in, and for the people he’s reliving it with to be his wife, the harpist and songwriter Joanna Newsom, and their young daughter.
Their days at home are placid. There’s a piano, mostly used by Newsom. (Samberg’s repertoire reaches its outer limit with the two-note melody—duh-duhduhduh-duhduhduh-duhduhduh-duh—from Ol’ Dirty Bastard’s “Shimmy Shimmy Ya.”) There are three harps, also mostly used by Newsom: two for mom, one toddler-sized, a gift from Newsom’s preferred harpmaker. He’s confident Baby Samberg will get around to making dick jokes sooner than later, but for now she’s taking after mom. “She's not bad,” he says. “She watches her mom and emulates that sometimes, and it's the cutest fucking thing I've ever seen.”
At night, Newsom mans the grill. Samberg, who’s been perfecting his Paper Planes and Bourbon Brambles, delivers drinks. They’re doing what a lot of other couples are doing. “We are those cliche fucking people right now watching Mad Men for the first time and then making cocktails.” (“I'm friends with [Jon] Hamm and I don't think he knows,” he says. “So maybe this is how he finds out.”) He’s checking Eater aggressively, and ordering increasingly ambitious takeout. If you’re wondering who delivers the best Nashville hot chicken in Los Angeles, Samberg is practically bursting to share his answer. (It’s Howlin’ Rays.) Newsom cut his hair recently, delivering what I can confirm is a perfect fade. She just used scissors, only breaking out the little electric Peanut razor to clean up the neck—a real pro, Samberg says, transparently delighted.
The work isn’t paused, exactly. He’s been doing some press for Palm Springs, and jamming away on development for Party Over Here, the Lonely Island’s producing shingle. They opened shop in 2017, and had something of a banner year last year, developing two of 2019’s best-loved TV comedies in I Think You Should Leave with Tim Robinson and PEN15. “I never woke up any morning being like, ‘I want to produce,’” he says. The point was always writing and telling jokes, preferably with his best friends. “But it’s started to become something that's really cool. The moments where you get to allow people you respect and admire and think have cool new voices fulfill the things they want to do, it's really gratifying. The amount of attention those two shows got this year was so rad.”
Developing two buzzed-about comedies will certainly boost your reputation, but nothing gets scripts and projects sent your way like selling your indie movie to Hulu and Parasite distributor Neon at Sundance for $17 million...and 69 cents. (“Hulu insisted," he jokes. "I can't remember who exactly suggested it, but I'm pretty sure it was Hulu.”) That deal was meant to give Palm Springs a theatrical release. The pandemic means it goes directly to Hulu on Friday, along with a few socially distant drive-ins. This might be a blessing in disguise, Samberg notes. “There's definitely the box office part of putting out movies that I was dreading all over again,” he says. “Obviously I haven't had smash-hit success in that department,” he says. Many of the films he’s starred in have become cult classics—which is another way of saying that most of them have failed to make back their budgets.
He finds himself in an interesting spot, career-wise. A seven-year stint on Saturday Night Live assures you a degree of fame. The specific nature of Samberg’s Digital Short-pioneering tenure—his debut was roughly coincident with that of YouTube, where his clips continue to rack up hundreds of millions of views—put him on even more intimate terms with his audience. Seven more years showing up in peoples’ living rooms as Detective Jake Peralta on Brooklyn Nine-Nine, deepened that relationship even further, cementing him as the charming, funny-face-making guy inside the TV.
Palm Springs was supposed to be a little different—it was built in part to reintroduce Samberg to the world as the star of films like this, rather than, say, Hot Rod. “We talked about movies like Eternal Sunshine and Punch-Drunk Love, in terms of casting a comedian who is known for making people laugh and using something different in him,” says the film’s director Max Barbakow. And Samberg had that different something, costar Cristin Milioti tells me. “He gets very vulnerable and raw, and I was so blown away by that,” she says. “He's so good at that.” A gaping existential chasm opens up in front of a guy who just wants to have a good time. Samberg dives in headfirst.
It was all lining up, a lucky leap forward in a career that’s followed a relatively steady progression. Sure, his movie wouldn’t come out in theaters. But it would be released on the platform that already hosts the shows that made him famous, where his fans know him best. He was grateful for his mellow quarantine. He was delivering cocktails to his grillmaster-wizard-harpist wife. He was catching up on some sorely needed pretend-mermaid playtime with his daughter.
By the time we spoke, Samberg’s mellow time-loop had gone a little wobbly at the edges. Coronavirus cases were spiking in Los Angeles, junking our plans to meet for a second interview. The protest movement had called into question the viability of his day job—could Brooklyn Nine-Nine exist in a defund-the-police world? A season spent contemplating the quiet joys of repetition had given way to something more like real life.
Don Rickles had the insult. Jerry Seinfeld had the quotidian gripe. Andy Samberg, to his occasional chagrin, has the comedy rap song. Pretty much the only job he ever wanted was SNL, basically organized his life around getting there. He transferred from UC Santa Cruz to NYU’s film program, did standup for a while after college, and suffered through what he describes as a miserable audition for a sketch-comedy theater, since it seemed like that was another viable path to Studio 8H. But the bits that really worked—on his way to SNL, as well as during his time there—were the videos, many of them song-based, he made with his junior high best buds Akiva Schaffer and Jorma Taccone. All three had grown up on a diet of golden-age hip hop, getting into rap and reggae while attending Berkeley High. And when they reunited in L.A. after college, they recognized that, since none of them could sing, rapping could be “a wonderful delivery system for jokes,” Samberg explains. Their relationship to the form is complicated: “There's strangely no one who dislikes comedy rap more than us,” he says now. “It just happened to be something that we started doing as a joke, just for ourselves, that people really enjoyed.”
The group honed its craft to a laser-sharp, transcendently dumb point, calling themselves The Lonely Island and posting videos online. Those videos got them a gig writing jokes for Jimmy Fallon’s MTV Movie Awards hosting gig in 2005, and on Fallon’s recommendation, the group scored SNL auditions. Lorne Michaels was charmed, signing all three—Taccone and Schaefer joined the writing staff, while Samberg was hired as a cast member. “Lazy Sunday,” which saw Samberg and Chris Parnell vigorously rapping about cupcakes and The Chronicles of Narnia, aired in December 2005; that week, traffic to an upstart video-hosting site called YouTube jumped by more than 80 percent. The Lonely Island would go on to produce more than a hundred more shorts for the show. He was always better known for his pretaped shorts than for appearing in live sketches. His Nicolas Cage impression radiated an intensely appealing psychotic bliss.
To a degree, Samberg and his friends were just doing what made them laugh. And while Samberg’s goofy affect and floppy haircut could give the impression that they weren’t thinking terribly hard about the process, they were comedy technicians. Real grinders. And beyond that, they were cognizant of how easily their work could tip into iffy territory. “To be blunt,” Samberg says, “being a white person making comedy raps is a dicey game. And we were aware of that from the start.” So they approached the genre from a place of love, stapling dick jokes to in-the-know allusions to deeper-cut rap and R&B. Perhaps more importantly, all their work adhered to one rule: We have to be the butt of all these jokes.
And so Samberg’s characters, buffoons in an ever-expanding universe of dipshittery, were always the punchline. They’d jizz in their pants, and bang their friends’ moms, and brag about recent acts of intercourse, never the wiser that the jokes were on them. Over time, The Lonely Island’s body of work coalesced into something like a definitive case against white-bro masculinity. This, too, came from experience. Growing up, he says, “the really aggro, macho dudes were the ones that we didn't really jive with. You get older and you realize a lot of that is learned and taught, and not necessarily the fault of a kid. But making fun of it is always funny to us, making fun of dudes that are sexist and homophobic and all that.” (His thinking has evolved there, too: “The way that you make fun of that has evolved, even. There was a time when, for us, the way that we thought it was really funny, you can argue was gay panic.”)
That people might not be in on the joke was an occupational hazard. “The fear with comedy is that people will like it for the wrong reason—like, that's your worst case scenario in success,” he says. “I’m on a Boat,” a song about assholes on a boat, has become a sort of anthem for assholes on boats. Such are the limits of comedy rap.
Sometimes a blunter approach is required. Co-hosting the 2019 Golden Globes, Samberg smuggled a not-quite-joke about Ryan Coogler’s Black Panther into his opening monologue. He posed a question to the director, all well-meaning but catastrophically ill-equipped white guy: "Ryan, were there, like, a bunch of old members of the actual Black Panther Party saying, 'I can't even get an audition?'” The camera cut to Coogler, who looked befuddled. Samberg, all in one breath, quickly undercut the premise: “Just kidding, they were all framed and murdered for wanting justice and equality. The world is and always has been a nightmare; it just seems worse now because of our phones."
“It's not even really a joke,” Samberg says when I ask him about it. “The joke is, I'm just saying the government fucked over the Black Panthers. The joke is that I'm setting it up by making it seem like it's going to be a super tone deaf, wack joke.” He’d met Coogler a few times, knew they were both from the Bay, was blown away by Fruitvale Station, Coogler’s 2013 film about the police murder of Oscar Grant, and needed to write some jokes about Black Panther.
It was less a chance to get political, he explains, than just a good joke, and one he felt prepared to tell: “That's something that I know about for real, [that] I've read about and learned about,” he says. Also, it killed at rehearsal: “I wanted to say it because when I did it in the read-through, everyone laughed and was like, ‘That's cool. That's a good thing to say.’ And I was like, ‘Yeah. It feels right.’” He was the butt of the joke. He also got the laugh.
When Samberg and I speak, the protest movement sparked by George Floyd’s murder by Minneapolis police has entered its third month. Statues are being torn down, university buildings renamed. For the first time maybe ever, the role of policing in American life seems up for debate. But the fate of shows about police is altogether cloudier. Cops and Live PD have been canceled, while shows about so-called “good cops” have come under scrutiny. Things seem somehow trickier for a comedy like Samberg’s Brooklyn Nine-Nine, which is thought to excessively sanitize police. In our moment of crisis, Nine-Nine’s well-intentioned approach seems perhaps not up to the moment.
Samberg is quick to acknowledge that reality. He’ll also note that “I just don't feel really like I'm the person to make any grand statement about it. I know this is what everyone's saying, but it's the right thing to say, which is: I'm really more in listening and learning mode.”
When I ask about the new landscape the show will have to contend with, he slows down. He takes his time before answering, seems a little anxious, wants to get it right. “We don't have the answer yet. I'll tell you that,” he says. The writers have gone back to the drawing board with their plans for season eight, he says, “and also taken a break to give it a beat, and feel what's going on a little more, and read more.” The whole team has been reading about police representation in film and television. Showrunner Dan Goor and the cast donated $100,000 to the National Bail Fund Network.
Samberg has been thinking about the limits of the show’s effectiveness, its power to do what it set out to. “We've done, quote-unquote, ‘the best we could’ so far,” he says. “Could we have done more? Of course. Anytime anyone's in a position where they're asking themselves, ‘Could I have done more?’ the answer is always yes. It's about what the goals were, and for us, the goal, maybe naively so, was more about laughs. We were making a workplace comedy and we tried to acknowledge the things about policing that were not ideal along the way.” He knows they’ll have to do more.
It’s not an excuse, but it’s worth noting that Samberg was a little hesitant about playing a cop to begin with. “I didn't grow up being like, ‘Trust and love the cops,’” he says. But, he notes quickly, “I also didn't grow up Black or Latino and have to actually be fucked with.” Early on, he’d joke with his castmates about how odd it was, that this squad of professional funny people had wound up wearing prop guns in prop holsters.
At first, it was easy enough to skip past that concern. His contract had run out at SNL, and, feeling a little burnt out from producing his weekly shorts, he’d declined to renew it. He didn’t have interest in leading a network sitcom, necessarily, but he’d made it a personal rule to do whatever Tina Fey and Amy Poehler did, and they’d both done that. “That has never steered me wrong. They are smart and good,” he says, laughing, aware of the understatement. He felt a particular kinship with Poehler, thanks to what he calls a shared “buoyancy in our styles.” When the producers Mike Schur and Dan Goor came calling, he was ready to listen. They’d built Parks and Recreation around Poehler, and though Samberg doesn’t watch much network TV, the connection helped: “Parks and Rec was a fantastic show and I loved it, and my wife loved it, and we watched it, and I love Amy, and I love Mike Schur,” he says, all bubbly effusiveness. “And he and Dan Goor asked me if I wanted to do another one of those, basically, and I was like, ‘Shit, I have to say yes.’
The show was sweet, a strong ensemble buoyed by Samberg’s cheery clowning. He won a Golden Globe after the first season. He was goofing off, but he was growing, too. His Nine-Nine character Jake Peralta is a typically joyful Samberg dingus, a detective frustrated that his job doesn’t more closely resemble Bruce Willis’s in Die Hard. The show’s ratings wavered over the course of its five seasons on Fox, but the audience it did retain was devoted enough to help it find new life—two seasons and counting—on NBC. That adoration could be credited in part to the series’ willingness to tackle, if awkwardly, the real-world issues that cut against the Nine-Nine fantasy of kooky, kind-hearted cops. The show devoted plotlines to workplace sexism, corruption, and, most strikingly, racial profiling: one episode finds Terry Crews’s off-duty police sergeant harassed by a fellow cop, and focuses on a conversation he has with Andre Braugher’s precinct captain. Two Black cops debating whether one should come forward with a potentially career-hindering accusation, the whole thing written by a Black writer, Phil Augusta Jackson: Hollywood is no one’s idea of an equitable space, but this had to be better than the alternative, right?
The cast and crew always knew that their television show wasn’t the real world, anyway, Samberg says. “We've always seen the show as a fantasy of what we would like the world to look like,” he explains. The whole project represented a kind of liberal wishful thinking: “Wouldn't it be amazing if there was a precinct like the Nine-Nine, this core group of detectives that has the moral compass you would wish for, and is truly diverse and represents a lot of different people?”
But the next episode of Brooklyn Nine-Nine will air in a world transformed first by a pandemic and then by a reckoning over the role of policing in American life. Things will change: Terry Crews has said that the show’s writers junked an initial run of four episodes they’d already written, and it’s all but certain that the show will address our new moment. It’s going to be hard, Samberg says, and though he’s wary of sounding defensive, he has a point. Because even an adjusted Brooklyn Nine-Nine will still have to deliver ratings, and appeal to an audience that sees it as a source of comfort, not provocation. “We're going to be striking a balance between doing that”—reckoning with decades of police brutality—“and putting on a show that people who love [it] have been watching for seven years,” Samberg says. “And they're expecting something specific, especially with comedy.” Whether audiences will be ready to laugh along with their favorite detectives again—whether the show’s breezy tone can persist in a defund-the-police world at all—is an open question.
The trick of it, really, is that his tried and tested tools aren’t of much help here. “There's nothing funny about what we've been seeing from the police,” Samberg says. “It's not a laughing matter.”
When Samberg was in his early twenties, cobbling together standup gigs and shooting early Lonely Island videos, he read an interview that Will Ferrell had given. This would have been smack in the middle of Ferrell’s legendary run on SNL, and yet here was Ferrell, holding the only job Samberg had ever wanted, explaining that even he was waiting for the whole adoring world to realize he was a fraud. The realization hit hard. “Me at that age, reading that about him at that time, thinking he is maybe the funniest person to ever live, period, [I] was like, ‘Oh fuck, there's no end.’ You're never on solid ground,” he tells me during our second talk. That feeling, he explained, never really went away—not when he got the SNL gig, not after he shot to fame on the show. And not now, either, not really. “I'm more secure than I was,” he says. “But I don't trust it.”
This echoed something he told me in our initial interview. He’s worked hard, he said, to find the work-life balance that being a father and a husband requires; trading the chaos of SNL for the network order of Nine-Nine has helped. But no matter how full his calendar gets, he still struggles to turn down bucket-list gigs. “I'm not out of the mindset of, like, ‘Holy shit, I got asked to do blank. I have to do it, or else I'll never get to do it again,’” he said. If he says no, well—what if he doesn’t get asked again? Theoretically, he’s been playing with house money since leaving his dream job in 2012. But that doesn’t mean the house can’t change the rules. “Somewhere I do genuinely believe it,” he said. “If you don't take the opportunities when they're there, they'll go away.”
So in 2019, Samberg shot the seventh season of Brooklyn Nine-Nine. He said yes to co-hosting the Golden Globes, and also to going out on a Lonely Island concert tour. He made a sublimely weird “visual poem” about Mark McGwire and Jose Canseco with Akiva Schaffer, too, under the logic that their most seemingly bird-brained ideas (“Jack Sparrow,” notably) had an odd way of finding enormous success.
The Palm Springs shoot had to be crammed in there, too, somewhere. He gets sent lots of potential scripts, but this was the rare one that checked all his boxes. The tone was there—it could benefit, even, from a dose of Lonely Island chaos, and the kind of beefed-up romantic arc they’d learned matters while working with Judd Apatow on Popstar. It was the sort of genre-bending movie he’d pay money to see, just as a civilian. That felt good. Perhaps most importantly, he thought he could actually do the part.
This was not an insignificant consideration. “In the beginning I was like, ‘I definitely am not a good actor,’” he says, bluntly. He’d always felt a little weird about acting, generally, his Lonely Island antics a rebuttal to theater-kid talk-about-your-craft work. A role opposite his pal Rashida Jones in the rom-com Celeste and Jesse Forever helped shift his thinking, as did a strangely touching scene opposite Adam Sandler in That’s My Boy, “which is an insane movie,” Samberg says. “It feels weird to say it, but when we shot that scene, I remember afterwards being like, ‘Oh, that was kind of nice.’" By the time Palm Springs came along, he was feeling a little more confident in his resume. “I feel like I've gotten a little better at acting,” he says, “having done so much of it over the last 14 years or whatever.”
The shoot was a blur, with Samberg juggling his biggest movie role in half a decade with the hundreds of small-bore decisions required of a producer. Constant conversations about the number of takes they’d have time for. Reminders of the degree to which they were falling behind schedule, of the killer bits that would then have to be cut. Initially, he’d thought he could maybe borrow a trick from Sandler and bring the whole family up to Palm Springs for a few months. For reasons of budget (the shoot lasted three short weeks) and tax rebate (Palm Springs was played by scruffy Los Angeles suburbs), that plan was scrapped. But the tradeoff, he says—he’d make that again in a heartbeat. “The reason to make an indie—to, like, eat shit on getting paid money and having a good schedule and having a good trailer and all of the cushy movie amenities,” he says, “you forego that because you're creatively excited about what you're doing. That was definitely this.”
The film’s gotten great reviews so far, easily the best of Samberg’s career. There’s that huge sale number they scored at Sundance, too, and the producing work that’s geysered into the Lonely Island office, past the songwriter Babyface’s piano and onto Samberg’s desk, as a result. (It’s Babyface’s old office.) The corona-affected release, of course, means Samberg won’t have the chance to break his opening-weekend curse, and what becomes of Brooklyn Nine-Nine remains a thorny problem yet to be solved. Challenges, sure, but also not more than that.
The whole thing reminded me of the way he described the appeal of Palm Springs's script. “It was well-written, and mixed with real comedy. Which, for me, is how life feels," he'd said. “It's miserable and terrifying and wonderful and beautiful.” He chuckled. "And in the darkest moments, comedy rises out of it.”
