The actor, best known for playing Sam on the Fox phenomenon Glee, stars opposite Lindsay Lohan in director Janeen Damian’s film about an arrogant hotel heiress (Lohan) who suffers amnesia in a ski accident and finds herself in the care of a lodge owner, played by Overstreet, amid her struggle to recall her former life. The project has been touted as a comeback vehicle for Lohan after a long stretch away from leading roles, but it also serves to reintroduce a wider audience to Overstreet, who has been steadily recording music over the years and is part of the cast of the Apple TV+ comedy series Acapulco.
“People that dive into my music might get a better sense of me, but I don’t feel like people really know me,” Overstreet, 33, tells The Hollywood Reporter. “People might know a character I’ve played on Glee. With people that love comedy, there’s also a tragedy to them. I’m a very emotional person. It might be overly emotional, which is why I write music, because it’s my one therapy outlet.”
In a candid conversation about the ups and downs of his past and his optimism for the future, the star explains why his connection with Lohan was a special one, how he navigates the challenges of the music industry, the bond he feels with his former Glee co-stars after the difficult times they faced together, his thoughts on Discovery+’s planned Glee docuseries and his obsession with romantic comedies.
How did you get involved with Falling for Christmas, and what did you know about the project heading into it?
My agent called me and was like, “Would you be down to do a chemistry read with Lindsay for the movie?” Knowing Lindsay’s pedigree, I was like, “That’d be awesome,” because I think she’s so freaking funny and super talented. I responded to the script because it reminded me in a great way of Overboard — I’m a huge rom-com fan. I was like, “Oh, I would kill to do something like this.” Especially with somebody that’s such a pro like Lindsay.
Originally, they wanted me to read for the role of Tad, who was the fiancé. I was like, “I can do an English accent, but I feel like I’m not gonna be as good as someone who’s actually English. Can I just read for the other role?” And I read for it and got it.
What do you remember about first meeting Lindsay?
I’ve done several table reads, and I’d never really done a table read like that with somebody to where I felt there was immediate chemistry. She was very giving, and it flowed really effortlessly between us. I was like, “Oh, this is gonna be really fun.” As far as my experience on that film, it was one of those things where she couldn’t have been more open and sweet when it was coming to working together, to where it was just a really easy environment. We had the scenes how they were written, and then we both tweaked and worked on them together and tried to make them better.
With this being touted by some as Lindsay’s comeback moment, did there feel like a sense of pressure to make sure it worked?
I think there’s pressure. You feel pressure with any movie and any project that you do because you want to make it as great as it can be for the fans and for people that are watching the movie — and at the same time real. But I think when we were working together, there was such an openness with both of us that it never felt like there was pressure.
You’ve had continued success with your music, but this project gives your acting a chance to be in the spotlight again. Fans are talking about a comeback for Lindsay, but can you relate to that as well for your own path?
Yeah. It’s interesting because I took a break from acting as soon as I finished Glee where I was like, “I want to take a break and just focus on music because that’s so important to me.” That’s where I come from. My dad [Paul Overstreet] won BMI song of the year five years in a row; he’s a Grammy Award-winning songwriter, in the Songwriters Hall of Fame. I grew up doing music, and that was such an important part to me.
But also the acting is such an important part of who I am, and that’s something that I love as equally. It didn’t necessarily feel like a comeback, but I had taken a break from it for a bit to where I was really excited to get back into it in that way. Iron sharpens iron, so working with somebody that pushes you and is also really talented and great, it made me rise to the occasion and do something fun again.
You’re really dedicated to comedy, which is a genre that appears to be in a strange moment. But your Apple TV+ series Acapulco is absolutely the kind of show that feels like it could be a huge hit.
I auditioned for that show in Mexico — my self-tape was at a resort in Mexico. I immediately connected with that character, and getting to play that goofy comedy thing, it was right in my wheelhouse. This feels effortless to me. This is what I was meant to do. I couldn’t pick a better job than that with Acapulco, and it’s so funny. I’ve done shows before, obviously, but that show is one where, weirdly, I’m a fan of the show. It’s so fun. It’s so refreshing. It’s so unique. We have a lot of freedom to where we can mess around and play around with a lot of stuff.
Does it feel like there’s currently a different conversation within the industry, or with public perception, about where your career is going? Are you on the path toward where you want to be in a couple years?
I feel like it’s definitely headed there. There’s a real big lack of romantic-comedy movies because I feel like everything has been very serious as far as entertainment goes. We need comedy and laughs and bringing people together more than ever. The serious, heavy, crazy stuff is great because it’s entertaining stories, but I feel like the more you can laugh, the more that stuff works as well. I go back, and I’m watching Notting Hill, and you can’t take your eyes off of Julia Roberts. Hugh Grant is the most charismatic person in the world. You see these movies, and you’re like, “Why aren’t there more of these right now?” You’re still watching those 20 years later. I could literally geek out on rom-coms forever.
I’ve seen your former Glee co-stars Kevin McHale and Jenna Ushkowitz tweeting about how proud they are of your success. Darren Criss and Adam Lambert are on the Falling for Christmas soundtrack. What’s it been like to know that the Glee family is still in each other’s corner?
With those specific people, it’s like we spent so much time together, and we are still a family. Every time we get together, it’s like no time is missed at all. We pick up right where we left off, and if those guys do anything, we all support each other. It comes from genuine love, and it literally feels like family. The fact that I got to do a soundtrack with Darren, that he’s on board, it’s like it’s a full circle. It’s so cool because how many different shows can you do with somebody where you end up doing music, and you’re doing a soundtrack with somebody that you end up on? It’s just honestly really cool.
Your Sam-Mercedes (Amber Riley) storyline from Glee is still such a great one.
One of the cooler parts of working on that show was probably the relationships I made individually with the people. Amber [Riley] texted me the other day, and she was like, “Hey, I heard this song that you had. I didn’t know this was you doing it. I love you so much. This song is so great.” There’s really so much positive reinforcement, especially with mental health — people that are just constantly encouraging you that you have this relationship with. They’re just such kind people.
There’s a Discovery+ show in the works about the making of Glee, and it sounds like the cast won’t be involved. Does it surprise you that there’s still this interest in the dramatic side of it?
It doesn’t surprise me because the show was such a monumental show in diversity and pop culture and really bringing attention to a lot of things that hadn’t been brought attention to. And we — I don’t want to say “we,” but the people that were creating the show — were pioneers in dealing with issues that hadn’t been dealt with before. But as far as the documentary goes, I don’t think anybody that’s really involved in the show has anything to do with the documentary. (Laughs.)
In my personal opinion, the documentary is trying to exploit the negative headlines and not celebrate the fact that we dealt with a lot of really heavy issues. We went through a lot together, and I don’t know anybody that’s involved in the documentary that I know. (Laughs.) It’s just one of those things where I feel like that’s a headline grab.
So many of your former co-stars are still thriving in the industry. Do you think you’ll try to see Lea Michele on Broadway?
I would love that. I’ve seen her up close and in person, and I don’t think there’s anybody like her that can do what she does. I don’t want that to sound like I’m tooting her horn. I’ve worked in this industry long enough time to where I’ve never really encountered anybody like her.
What’s been getting you most excited lately about music?
I have a Christmas song in the movie and been doing music as much as possible. The one thing I’ve never done is I’ve never put a full-length record out. I would love to be able to make a body of work, whether it be an album or several albums, that in 30 or 40 years I look back, and I’m like, “Man, that is something I’m really proud of.” Music is a very single-based world to where there’s not as much attention on a full-length album. Regardless of how people consume music, I would love — just for my own artistic sake — doing a full record, basically painting a picture.
You seem surprisingly thoughtful. Do fans know the real you?
I don’t think so. People that dive into my music might get a better sense of me, but I don’t feel like people really know me. People might know a character I’ve played on Glee. With people that love comedy, there’s also a tragedy to them. I’m a very emotional person. It might be overly emotional, which is why I write music, because it’s my one therapy outlet.
People that know me really well, I feel like I’m the class clown. I like to goof off. I love to try to get people to laugh and take a break from reality. And then there’s the other side of me that’s very overly emotional, which is why I feel like I’m meant to write music. The older I get, the more I want to just expose who I am and have people get to actually know me.
When you say “tragedy,” is that in your younger years, or just in your overall path?
As far as tragedy goes, I was very blessed with a great family and a great upbringing, and my parents are my best friends still. But when I got thrown into the machine that is the entertainment industry at a young age, I went through a lot of things that were unpredictable that — especially with losing people that are your best friends at a young age — you aren’t prepared to handle that. But I do feel like a lot of that makes you stronger and makes you more grounded, in a weird way. It makes you get to know yourself on a different level.
In terms of losing co-stars, does it feel unfair that you all had to go through everything that you did?
When [Glee star] Cory [Monteith] passed, he was my best friend who I spent probably 10 months a year with for three or four years straight, and I was closer to him than with anybody. Losing anybody young, you’re never prepared for what happens with that, and then when there’s a big microscope and lens on that you, you’re dealing with that in a completely different way.
But I do think that that makes you stronger. Losing anybody young is really challenging, but it makes you tougher, and it makes you more resilient. It’s different losing somebody at a young age and then losing somebody that everybody knows about, and they’re asking questions and talking about it, and it’s in your face, and you’re figuring it out.
I know a lot of people, fans included, were really impacted by Cory’s death, so I can only imagine what it was like for the cast.
Cory, it’s just one of those things where you can’t really put your finger on it, and none of it makes sense. Loss never makes sense. I went into a hole, writing songs and stuff, to cope with that. It’s like it’s therapy in itself. But the community around me was so beautiful and so caring that it was just great to have that family.
It’s just one of those things where there’s no making sense of any of it. But it really makes you appreciate the time that you have and the loved ones around you. Hug as many people as you can while you can, and just love blindly. That’s the beauty of the mortality, is just really, really loving on people you can, while you can.
That’s why I love comedy, too, and the kinds of projects you’ve been choosing. It can really feel life-affirming to get to laugh with other people.
That’s the beauty of comedy. You’re celebrating life, and that is, to me, the biggest thing: if you can share, if you can hug. Love as many people while you can, and bring joy to people. As an entertainer, if I can make anybody laugh and smile, that’s what you want to do.
Interview edited for length and clarity.
Falling for Christmas is now streaming on Netflix.