Out and proud performer Anthony Rapp is celebrating his new life in Chicago with Home for the Holidays this season. This December, he presents an intimate show for fans inside the Lookingglass Theatre Company space right on the Magnificent Mile. Accompanied by Rick Bertone and supported by various local talent, Rapp has curated a variety of tracks to warm any Scrooge’s heart.
He began a career on Broadway in The Little Prince and the Aviator in 1981 and appeared onscreen in 1987 for Adventures in Babysitting. Film appearances include School Ties, Six Degrees of Separation and A Beautiful Mind, among many others.
Other Off-Broadway, Broadway and tours followed, but the musical Rent changed the trajectory of his stage career in a major way. Lead parts in You’re a Good Man, Charlie Brown, Hedwig and the Angry Inch and If/Then followed. He created a one-man show based on his memoir Without You and is set to be Benjamin Stone in Porchlight in Concert’s production of Follies in April of 2026.
He met success on the television series Star Trek: Discovery, playing Paul Stamets, and sang on multiple albums throughout his musical journey over the years.
Anthony’s latest chapter has him returning to his roots and moving husband Ken Ithiphol, along with two sons Rai and Keony, to Illinois.
Rapp took time out of rehearsals and juggling a busy home life to talk about his upcoming holiday show at Lookingglass Theatre.
Windy City Times: You were born in Chicago?
Anthony Rapp: Yes, and I live in Andersonville now, not that far from the hospital where I was born at Swedish Covenant.
WCT: We are neighbors and you have picked a great place to live.
AR: Absolutely. I grew up in the suburbs and would come to Chicago to work as a kid. I have come back to Chicago on tours, but it’s been very special to move back and make it my home.
WCT: Was there a specific reason that you moved here?
AR: Yes. My husband Ken and I have two young kids. We were doing fine raising them in New York and there were challenges, but when we visited friends and family here, we started liking the vibe. We began exploring the possibility of a change of pace and scenery.
Chicago has exceeded our expectations. I didn’t know you could live in the neighborhood in a city that has bunnies. Our kids delight in seeing the bunnies hop around and there is a nature path a block from where we live.
This is all in the city with accessibility to restaurants and culture. I grew up in the suburbs and it’s not my speed now.
WCT: How have your fifties been so far?
AR: It has been a total life shift. I thought parenthood had passed me by and I was always concerned about how I would do it as an actor.
After working with Sonequa Martin-Green on Star Trek: Discovery, I saw she had two kids and still worked so hard on the show. A lightbulb went off, then I realized it was possible and I could make it work.
It was during COVID that Ken and I started talking about having children. My fifties have been part of that whole journey, which has been transforming.
WCT: How do the intense fans of Broadway compare to Star Trek fans?
AR: When I do Star Trek conventions and I have my pictures at the table, I get as many fans picking up the Rent photos as I do with the Paul Stamets photo.
Both pieces of art speak to our best selves. They are about hope in the face of darkness and coming together when facing a crisis. Transcending our differences is in the DNA of both shows. They are both sincere and anti-cynical. It’s coincidental, but I think there is commonality.
WCT: How are they different?
AR: Star Trek fans can be obsessive over little details about every episode and the technical things.
People will speak about what Rent has meant to their lives and how it has shaped them. It might affect the career that they want or how they want to live their lives. This is different than being a fan of something they just enjoy watching.
WCT: How did you approach crafting this holiday show at Lookingglass?
AR: When I first started talking about it to the team, one of the things I was excited about was the possibility of assembling local talent and getting to know them. I approached it by holding auditions and hearing songs they wanted to sing. We had six slots to fill and by bringing those puzzle pieces together, we shaped it from there.
I hoped someone would come in singing “River” by Joni Mitchell. It’s not a traditional Christmas song, but it’s a song of the season and speaks to the mood of the time. Alina Taber will sing it in the show after singing it so beautifully at the audition.
I was hoping for a great rendition of “Have Yourself a Merry Little Christmas” because it’s my personal favorite Christmas song and Grace Bobber made it her own while honoring the overall feel of it.
The approach that Solomon Langley took with “White Christmas” lit everyone up, so what people brought in shaped the show. I had ideas on what I wanted to sing and which group numbers we should sing together.
My longtime friend and director, Rick Bertone, and I built out what we thought the set list could be and hoped they would bring in those songs, which they did and we assigned a few songs.
The idea is honoring the traditional while bringing something alive, fresh and contemporary to it.
Someone brought in a funny song that no one had heard and it was entertaining, so now it’s a part of the show. I don’t think anyone has heard it before, but I might be surprised.
WCT: We can leave that as a surprise at the performances. Do you like contemporary holiday songs from singers like Kelly Clarkson, Ariana Grande and Sabrina Carpenter?
AR: Some of them. We had someone bring in a Kelly Clarkson Christmas song, but the other material rose above it. It was more about the right fit with the right person, if that makes sense.
WCT: Are you singing a holiday song from Charlie Brown?
AR: We are definitely singing a song from Peanuts because for me, that’s synonymous with Christmas.
WCT: Does this cabaret style allow you to take breaks during the show when a guest singer performs their song?
AR: The idea is we are inviting an audience into our living room for a holiday party. We are all hanging out onstage and there are no formal entrances and exits.
There might be a little backup singing moment or duet segments. It’s informal, comfortable and cozy. We are all human beings sitting in the room together. That’s the kind of theater that I love, where there’s no barrier between the audience and the performers. Not that I am demanding sing-alongs, but there might be some. We are all here together in cold, dark times to bring each other a little comfort.
WCT: Is the show appropriate for people of all ages?
AR: Yes, I don’t think there is any cursing in it.
WCT: Was there a holiday song that you refused to add to the show?
AR: I told everyone from the beginning that it should be secular. I didn’t want to alienate anyone with any kind of religious content. The respectful path was to keep the spirit as general and not any specific religion.
WCT: Your next project is with Porchlight Music Theatre. Have you performed at the Studebaker before?
AR: I honestly wasn’t familiar with the Studebaker and I had heard about Porchlight, but didn’t know them directly. I did know Follies, though, and when I was asked, I felt very honored.
I have sung some of Stephen Sondheim’s songs at events and I have had the pleasure of meeting him a few times, but to do this show at this time in my career is exciting.
WCT: Is there a Broadway musical that you would still like to do, but haven’t yet?
AR: I have been close to being in Cabaret a number of times, but couldn’t do it because of conflicts. I would love to play Emcee. I remember seeing Joel Grey’s performance when I was eight-years-old and it’s a role that is epic to me.
WCT: Do you still talk to Idina Menzel? She was very down to earth when I was around her.
AR: Yes, she has always been authentically herself from day one. When Frozen took over the world, she was the same artist as before and would go perform at the Oscars, then return to our show. She is always committed to the work, no matter how famous she gets.
WCT: Speaking of talent, your brother Adam wrote the book for The Outsiders: A New Musical. Are you planning on attending the premiere in Chicago this coming February?
AR: I didn’t know it was coming, but I will be there. I have been a fan of his ever since he started writing in high school. He is one of the most dedicated writers I have ever known and is so prolific.
My brother has been critically acclaimed, but it has taken him a while to reach this level of outward success. Believe me when I say he’s earned it.
WCT: What advice would you give performers auditioning for Broadway?
AR: My advice is to stay grounded while being connected to your spirit and heart. Always remember what you love about the work because the business part is always changing and can be really challenging.
There’s a lot of noise and in the age of social media, people can become inundated by feedback, both negative and positive. It can lead to opportunities, so they should use the Internet as a tool, not an end goal.
Just stay connected with the person in the room acting in the scene in front of the audience. That’s why we do what we do. All of the other stuff is just noise.
Anthony Rapp: Home for the Holidays makes the season bright at the Joan and Paul Theatre at Water Tower Works, 163 E. Pearson St, from Dec. 17-20. Find ticket information, including two performances on Dec. 20, at lookingglasstheatre.org.