Ryan O'Connor
(© KC Perry)
Ryan O'Connor
(© KC Perry)
Ryan O'Connor's path to the spotlight has been a circuitous one. Trained as a stage actor in New York, he headed out to L.A. -- where he found small parts in movie and television -- before finding a larger audience on YouTube. Now, he's in the midst of his first live comedy tour, Ryan O'Connor Eats His Feelings, which has upcoming gigs at Davenport's in Chicago on July 7 and 8; Harlan's Cabaret in New Hope, Pennsylvania on July 11; and Joe's Pub in New York on July 19. TheaterMania recently spoke to O'Connor about this show and his career.

THEATERMANIA: What made you start posting videos on YouTube?
RYAN O'CONNOR: I was really frustrated with my career. I had a couple of great years in LA, but nothing big was happening. So one night, I decided to watch every episode of the [title of show] show, Jeffery Self's video blog, and Andrew Keenan-Bolger's video blog, and I instantly decided I wanted to be part of this community. So I filmed myself in my bedroom -- I think in that first video I have remote controls talking to each other -- and while I hadn't originally planned on posting it on the Internet, I just put it up the next day and didn't tell anyone.

TM: So how did you develop a following in the theater community?
ROC: Initially, I hadn't tapped into the theater community. But in 2008, I was in New York with my best friend, Marissa Jaret Winokur, during Tony Award time; we even went backstage to see Patti LuPone after Gypsy. So my next video after that was my thoughts on the Tony Awards with Patti's speech from the Tony Awards behind me. Marissa posted it to her friends, and people started finding it. And so my video show went from being a pop-culture show to a more theater-specific one.

TM: How did you decide to start performing live again?
ROC: I left Circle in the Square feeling underconfident and self-conscious about my singing voice; they knocked me down but hadn't picked me back up. So I was focusing mostly on film and television. But in my videos, like in my life, I would just sing here and there, and enough people said that they liked my voice that it started to give me confidence. Then I got a call to do this show in Burbank called Red, and thank god, it went well. I did a song called "Naked" by Katie Thompson, and so I started to put an act together of Katie's songs -- and then I got the idea of doing an evening of story songs woven into my own stories. Then in 2009, I talked to my friend Colleen, who is better known as Miranda Sings, and I suggested we do a show together. So I called the Rrazz Room in San Francisco and pitched them our show -- which was really two shows where we each did half a set -- and they tried it and it was a big hit.

Artwork for Ryan O'Connor Eats His Feelings
Artwork for Ryan O'Connor Eats His Feelings
TM: So how did that show develop into Ryan O'Connor Eats His Feelings?
ROC: The title came from what I knew I'd be talking about, which would mostly be food issues. But I also knew it's tough to do a whole hour about food; and then I realized the term "eats my feelings" means I can sing and talk about anything. I remember Rosie O'Donnell once saying fat people are the last acceptable group you can discriminate against. Personally, I don't care what size you are if you love yourself; but I think that's rare for a fat person to really love himself.

TM: Would you go on one of those reality TV shows that make you lose weight?
ROC: I did audition for Dance You're A** Off even though Marissa was the host. I didn't tell them about our friendship and though my audition went really well, they finally looked at YouTube and then told me I couldn't be on the show. I actually ended up being Marissa's assistant. Then, I was up for Dieting with the Stars with Kirstie Alley, but that show got canned. I would do a reality show, but not one where it's you need to lose 100 pounds in three days. The thing is if I got thin, not only could I still talk about when I was fat in my own show, I'd actually have a better ending to it!

TM: You've been touring for about a month: What has the experience been like?
ROC: It's been really interesting and a lot of work. I anticipated it being hard and it's been harder. It's really just me and my boyfriend and best friend, and none of us have really done this before, so between us we're a lousy tour manager. And you never know what to expect. I thought we'd sell out Las Vegas, or at least find an incredibly receptive crowd, and it turned out five people showed up. But I think a handful of the five really loved it and that made it worth it.

TM: Was it a plan to make New York the last stop on the tour?
ROC: Yes, New York will see the show in the strongest shape it can be in. Even now, when a show doesn't go so well or when an audience may not get something, I know the New York crowd is going to get it, so I don't worry about it. I'm still waiting to hear who the special guest will be for the talk show segment I do in every city; but I promise you that whoever I get, any theater fan will not be disappointed. And one more thing -- although it hasn't happened yet; there's a place in the last song where I could moon the audience. So people who really want to be sure they don't see my butt will just have to leave before the last song. .