“God, this is tough to answer without sounding like a jerk,” says Skylar Astin before pausing for thought. The question probably feels tough because it requires him to blow his own trumpet: something he seems a bit too polite to do. But seriously, why has the 33-year-old singer-actor always had plenty of work? Since his breakthrough role in Broadway rock musical Spring Awakening 15 years ago, he’s racked up 35 screen credits in everything from the Steve Coogan-led comedy film Hamlet 2 to cult musical dramedy series Zoey’s Extraordinary Playlist. Then of course there’s his star-making turn in the Pitch Perfect movies as affable a cappella singer Jesse Swanson, boyfriend of Anna Kendrick’s Beca Mitchell.
Because he’s a pro, Astin finds a way to tackle the question that doesn’t sound arrogant. “What I will say is this,” he continues, speaking on Zoom from his home in LA’s San Fernando Valley. “I don’t know if this is the reason why I’ve gotten work but something very important to me is having good working relationships. It’s really easy to be a dick in this position. If you’re walking onto set as the number one lead, you can be a nightmare – and technically, people will have to deal with that because there’s this kind of built-in hierarchy, unfortunately. But coming from the theatre, I never subscribed to that.”
“It’s really easy to be a dick in my position, but that’s not me”
When he’s on set, Astin always hangs up his costume after a scene, makes a point of thanking crew members, and doesn’t expect anyone else to fetch his water between takes. “I think that kind of work ethic and respect for everyone else is maybe what has gotten me far, or at least keeps me going,” he says. “Leaving the trail of a good reputation is important. You don’t want to leave people any way other than wanting more. But I don’t do that in a calculated way. It’s just the way I was raised.”
Astin’s work ethic is now fuelling a recording career that feels overdue. He has sung plenty in the past – he covered Kelly Clarkson‘s ‘Since U Been Gone’ in Pitch Perfect and even tackled Linkin Park‘s ‘Numb’ on Zoey’s Extraordinary Playlist – but until this year, he had never put out music of his own.
Astin says he’s been writing “piano-based singer-songwriter songs” for years, but the pandemic compelled him to make “lighter, poppier” music that he actually wants to share with the world. In June, he dropped his debut solo single ‘Without You’, a shimmering synth gem that conjures up images of driving through LA on a balmy summer evening. Then earlier this month, he followed it with ‘When You’re Not There’, a perky disco-pop track he compares to Justin Timberlake‘s ‘Can’t Stop The Feeling!’.
Both songs were written over Zoom with Eric Lam, a producer with connections to Astin’s family. “Eric sent me all these beats: little five-second clips that we would loop. And I really had fun writing hooks and building them out further,” he says. What started as a “fun experiment” soon coalesced into a Skylar Astin sound. “For a while, it’s been like: ‘What is my style? Is it more John Legend, or more Justin Bieber? But I think this genre kind of found me and I’m excited to take it further.” Astin has at least six other Lam-produced tunes in the can, but is now working with other producers too.
Eventually he wants to release an album, but for now he’s being “more careful and choosy” about what he releases. Astin insists balancing his fledgling music career with acting commitments won’t be a problem. “It’s already working out,” he says. “I’ve written songs in the past couple weeks that I’m really proud of, and so I have an appointment today [NME spoke with Astin in late August] with a producer to track some piano. I’m going to finish the vocals next week before I leave for Canada to film a movie. And then when I’m filming, I can remotely give notes and do some post-production stuff.”
Astin’s acting career predates his Broadway breakthrough in Spring Awakening, a role he landed when he was 18. Three years earlier, he was given his stage name – he was born Skylar Astin Lipstein – by Nancy Carson, a “very famous youth talent agent” whose previous clients included Ben Affleck and Matt Damon. Astin, who grew up in Rockland County near New York, the son of a garment industry executive and a homemaker, was bitten by the acting bug when he starred in a local production of Godspell at 13. He can still remember the precise moment he realised performing was his calling. “I stopped thinking about the lines, the choreography and my blocking and suddenly I just behaved as the character in that moment,” he recalls. “And I know now in hindsight that the director, Tim McDonald, who I still keep in touch with, had really found a way to shake me out of my head and be that character.”
With Carson championing him, the teenage Astin would be called into New York every few months to audition for a musical workshop. Eventually, after no fewer than 12 callbacks, he landed a role in Spring Awakening, a brand new musical that explored teen sexuality through an alt-rock-leaning score, then stayed with the production as it transferred from Off-Broadway to Broadway. “I remember feeling so unworthy, but also thinking, ‘I guess I’m here and this is my community,'” he recalls. “And that was a really empowering feeling, because I felt like I had nothing to lose.”
At that stage in his career, Astin says he never contemplated working anywhere other than Broadway. But because Spring Awakening was “such a hot show”, the entire cast of rising stars – including future Glee lead Lea Michele and Mindhunter‘s Jonathan Groff – would get invited to audition for film and TV projects. Astin landed his first one in 2008 when he was cast opposite Steve Coogan in Hamlet 2, an acerbic comedy film about a failed actor who reluctantly takes a job as a drama teacher. Astin plays Rand Posin, one of just two students who’s remotely interested in what he has to offer.
“Leaving the trail of a good reputation is important”
Working with Coogan was a challenge that Astin rose to. “For some reason, I had the guts to come out and improvise with him right away,” he says. “And I think that’s because he made me feel safe from the start.” Astin can remember witnessing a rather surreal example of Coogan’s comic brain in action. “He’s playing a recovering addict and there’s this scene where we, the students, spike his non-alcoholic beverage so he has this crazy LSD trip,” Astin recalls. “Steve was adamant that when he wakes up, he should be bottomless rather than shirtless. Adamant. He was like, ‘Nothing is funny about the torso – but someone’s ass in the air, that’s funny.'” Ten years after Hamlet 2, Astin and Coogan co-starred again on the comedy-drama film Hot Air. “He started giving me shit straight away,” Astin says with a laugh. “Like: ‘You really blew up.’ Because I guess when we first worked together, I was only a kid.”
Four years after Hamlet 2, having guest starred in Lena Dunham’s Girls and the Hugh Laurie medical series House, Astin landed his star-making role in Pitch Perfect. Co-starring Anna Kendrick, Rebel Wilson and Anna Camp – who later became Astin’s wife, though they divorced in 2019 – this infectiously goofy musical movie about a cappella singers became a huge sleeper hit in 2012. “I thought it was hilarious straight away,” Astin says, “but I did think: ‘Are people going to go for this? Is it too campy?’ But I’ll tell you someone who always knew [it would take off]: Rebel Wilson. From the first table read, when we were still figuring it out, she was saying: ‘You guys don’t understand – we’re not just doing one of these movies. Skylar, you’re going to be a heartthrob and we’re going to win all the Teen Choice Awards. I think it was half manifesting and half intuition on her part, but she’s a real smart cookie.”
Sure enough, Pitch Perfect won four Teen Choice Awards the following year including one for Astin. Before he reprised his role in the 2015 sequel, which grossed an impressive $287million worldwide, he played a fancy banker who falls for his janitor in the underrated sitcom Ground Floor. After Pitch Perfect 2, he starred opposite Nick Nolte in the political comedy Graves and appeared in the final season of Emmy-winning series Crazy Ex-Girlfriend. Along the way, however, there have been bumps in the road. “I’ve been part of many TV pilots that didn’t get picked up,” he says. “Some of my favourite TV shows never happened. I made one with [This Is Us creator] Dan Fogelman and we still text each other today saying: ‘How did that not go [ahead]?’ When that happens, it feels like a failed purpose, but you also feel like you owe each other something. Like, we gotta try again sometime.'”
Still, when asked to name his most crushing disappointment, Astin singles out the recent cancellation of Zoey’s Extraordinary Playlist, a quirky comedy series starring Jane Levy as a woman who can hear people’s innermost thoughts as songs. As Max, a coworker who has feelings for her, Astin has belted out everything from INXS‘s ‘Need You Tonight’ to the Jonas Brothers‘ ‘Sucker’ over the show’s two seasons. “It really upset me because I feel like we let down the audience,” Astin says. “They really came on a journey with us, and we were there for them in such a tough time during the pandemic. The show is very meta and cathartic in a way because it deals with grief and sickness and moving on. And I really wanted to move on with that show and audience through the post-pandemic world.”
“My Billy Joel biopic would focus on his struggles”
Asked about recent reports that streaming newbie Roku is reviving the show for a two-hour TV film, Astin becomes as adamant as Steve Coogan before a potential bottomless scene. “Oh, we’re doing it – I’m booked, boo,” he says excitedly. “I know there was a season three idea and maybe a season four idea, but now we’re going to do a movie and maybe we’ll do another movie [after that]. This one’s going to be Christmas-themed, and there might be a Valentine’s Day-themed [movie] after. And who knows, maybe we’ll get more seasons down the line? But right now, I’m just grateful that we get to do this movie. We’re filming it very soon.”
Astin says embracing a TV movie instead of a new season just goes to show that “this business is all about pivoting.” He’s happy to talk about his dream pivots for the future, which include a Marvel role and a Billy Joel biopic. “I’m a huge superhero guy, and I think I have the skill set to do something different with it,” he says. “Kind of like the way Ryan Reynolds and Paul Rudd have incorporated comedy, I’d love to play a superhero who’s not super-serious with a bit of wit.” As for Joel, Astin says he can envision a film that’s “not so big production-wise” as the Elton John biopic Rocketman. “I see it having a grainier vibe,” says Astin, who covered Joel’s ‘New York State Of Mind’ very well on Zoey’s Extraordinary Playlist. “Like, we’d really bring out the Long Island [in him] and focus on his struggles and that New York story of a piano man.”
Perhaps taking a leaf from Rebel Wilson’s book, Astin continues with his manifesting. “I think there’s a really artful way to tell his story, which is such an inspiration to me, so I’m putting it out there into the universe,” he says. But in the meantime, Astin has a simple aim for the way he conducts his music and acting careers. “I want people to realise I’m always being authentically, transparently myself,” he says, “and hopefully to love me for it, too.”
Skylar Astin’s latest single ‘When You’re Not There’ is out now