Skylar Astin on Stage, Screen, and in Your Living Room

Though most certainly recognizable as Jesse from the unexpectedly-giant hit musical-turned-trilogy Pitch Perfect, Skylar Astin has been a staple on stage for many years—from playing Tony in a Carnegie Hall production of West Side Story, to a hit one-off rendition of Stephen Sondheim’s Into The Woods at the Hollywood Bowl, and the lead in the Off-Broadway production of Little Shop of Horrors.

Moving away from musicals, Skylar Astin can now be seen in the new CBS drama, So Help Me Todd, opposite Academy Award winner Marcia Gay Harden.

Below, he sat down with us to discuss how a basketball-loving NYC kid turned into a musical go-to, the complexity of Sondheim, and why in between hit shows and blockbuster acapella franchises, he’ll always find his way back to the stage.

LEO: Where did you grow up and how did you first get into musical theater? 

SKYLAR: I grew up in Rockland County, New York, and I got into musical theater because my mother convinced me to audition for the local production of Godspell when I was about 13. I was coming back from basketball practice, and I had been playing piano since I was about five years old. I was always a fan of theater, but never had the guts to try it out for myself, and she kind of convinced me to do it, and thankfully, and due to a lack of boys auditioning, I got the lead role, and my life kind of did a bit of a 180 from there.

Could you tell us a little bit about your new series So Help Me Todd, and was there anything specifically that drew you to the lead role? 

I love Todd’s messiness. I love the idea that I get to play someone who’s kind of a black sheep of the family, who has his own point of view on what went down with his demise. He lost his private investigator license and is now struggling to get it back. And I just absolutely love the dynamic between him and his mother. It is totally like a buddy comedy between the two of them, but then again, there are so many great characters in the series that are going to really expand the world of this legal/private investigator comedy drama.

“I always want to be on stage when I’m not on camera.”

Were there any detective films or shows that you used as a reference point, or did you just jump straight in and make it your own?

I went straight in, but I was given a reference of Moonlighting, with Cybill Shepherd and Bruce Willis. I think that has a slightly different tone, but it’s very snappy dialogue, and ours is very dialogue heavy, and that’s something that Scott Prendergast, our creator, really enforced. Like, “You guys are going to be memorizing a lot of lines on this, because it’s got to be fast, and it has a total rhythm to it.” So, as a theatre performer, and Marcia Gay Harden being a theatre performer, I think we lend ourselves to these characters in a nice way that doesn’t feel so stiff and rigid.

What was it like working with Marcia Gay Harden? 

She’s the best. I’m very lucky. I’ve been a fan of hers for so long, and I kind of had an idea of what she’d be like, and she even surpassed my high expectations. She’s such a pro. She’s so lovely to work with and she has a lot of fun with it. And we actually get to do quite a bit of improv together, which is really nice.

Was that your favorite part of working on the show? 

It was all really great, but they do let me get away with a lot. I don’t like to just improv for improv’s sake. I’m never just going to add things because I want more lines. If it’s perfect as is, I will do that. I’ll always give them versions where it is completely on book. But if I find any little moments or opportunities, they don’t even have to be dialogue improvs, they could just be little physical manifestations that I put in there, I like to give Todd these little quirks that make him unique.

Photos by Ian Lanterman

Switching over to musical theater. Are there any upcoming projects? 

I just got off an amazing run in Little Shop of Horrors. I did that in New York, and I had the best time. So, I was just on stage, and I always want to be on stage when I’m not on camera. And so, I imagine for my hiatus, hopefully, I could work something out where I go back on the stage in some capacity.

Speaking of Little Shop of Horrors, this is the second or third time you’ve done a work by Alan Menken. Is this a coincidence or are you a big fan of his in particular? 

I’m a big fan of his work for sure and I was able to get to know him quite well the first time we worked together, because it was actually his first work that he ever did with Howard Ashman, who he eventually went on to do Aladdin and Little Mermaid and Beauty and the Beast with, and this was one of his early works, God Bless You, Mr. Rosewater. It wasn’t a big hit, but it showed his seedlings of brilliance. So, all these years later, he really got a kick out of revisiting the material, putting it up with professional actors, and we even made a cast recording of it. To see him kind of excited like a little kid was really fun, so that bonded us. So now, we know who each other are. But that offer to do Little Shop of Horrors came directly from the production itself and from the director, Michael Mayer, who I did that production of God Bless You, Mr. Rosewater with.

You’ve also performed in two Stephen Sondheim works. West Side Story, which he did the lyrics to, at Carnegie Hall. And Into the Woods at the Hollywood Bowl. Were you ever able to meet Sondheim in person? I’m assuming you’re a huge fan.

I love him. He’s my number one. I thankfully was able to meet him, but not when I was doing those works. I do know that he saw the Hollywood Bowl production, so that was really cool. And I know that he liked it because there was even talks of potentially doing it elsewhere before the pandemic kinda shut everything down. And the fact that he and James Lapine both approved of this production was such a big thing for me. I didn’t get to work with him in any intimate capacity, but I did meet him back in the day when he saw Spring Awakening. And I even met him when I was briefly at NYU, and we had a little chat in the waiting room. I’m sure he would never remember it, but I do, of course, so that’s my Sondheim story.

“This isn’t pop music where you can take liberties. There is a reason why he wrote every single dynamic in his score. It’s your responsibility when you do Sondheim to learn its complexity. That’s why people say it’s difficult. “

People say Sondheim’s music is particularly difficult to perform.

It’s complex. So even when you think you know a Sondheim song, there are these moments when you’re learning the music with the musical director where they’ll make these corrections that you’ve probably been singing wrong for years, or you’ve always been hearing a melody, but now you have to sing a counter melody or a harmony; define that, the rhythm, the lyrics. But the thing about it is, when you study it and when you do it, you learn so much. And in the learning of it, you understand why every moment is exactly where it is. There is a method behind every bit of madness. It’s like Shakespeare, in that you have to respect each quarter note, each rest; this isn’t pop music where you can take liberties and alt melodies and maybe back phrase a little bit, there is a reason why he wrote every single dynamic in his score and with his lyrics. So, it’s kind of your responsibility when you do Sondheim to learn its complexity. And I guess that’s why people say it’s difficult.

Is there a Sondheim, or any other musical actually, that you would really love to perform in but haven’t yet? 

Yes. A big dream role for me is to play George in Sunday in the Park with George. That’s my number one. I know so much about the artist. Artist and commerce mixed with art. I just think it’s a really beautiful, beautiful story and a brilliant character.

Is there anyone in the industry that you particularly look up to?

Of course! I love certain directors like Bartlett Sher and Alex Timbers, I’m a big fan of. I would love to work with them one day. I guess Sondheim is number one. I know he’s the topic of the day, but he is my number one. I really, really look up to him.

Finally, you’ve had success in television, film and theater. Is there any aspect of the industry or any other industry that you’d like to try, but haven’t yet? 

Directing and producing. And writing actually. I’ve written a fair amount of scripts and I’ve even sold shows to networks and gotten very close to being able to turn them into series. But, for whatever business decision, it didn’t completely happen. But it’s inevitable. It will definitely happen. And I’ve produced before, but I think directing is on the horizon. I know I’m good with actors, and I feel like I know how to talk to them. And as far as TV and film is concerned, if I were able to shadow a director through the pre-production process and really understand what it takes to prep an episode, I would probably start there and I would probably be starting on a show that I’m on like, So Help Me Todd, so I really know how the machine works and I’m not just coming into some foreign land, because that’s daunting even for very experienced directors at times. And then, who knows, maybe mount something on stage locally in California or a small theater somewhere just to kind of do it and work with actors.

Do you reside in California?

I’m from New York. That’s where my family is. But I have a house in LA and so I consider myself bicoastal.

Most importantly, which basketball team do you root for? 

The New York Knicks. All my teams are New York.



Premiering Thursday 29th September, as Todd in So Help Me Todd


As Jesse in Pitch Perfect

As himself in the HBO documentary Spring Awakening: Those You’ve Known