Second City Actress Sam Bailey Talks Earlier Challenges And New Webseries “You’re So Talented”

By: Denishea Bright

Everyone knows what self-doubt is like because it puts a sour taste in our mouths, all beautiful sounds are mute, it’s a down and out feeling, it smells like everything but success, and worst of all you can’t see the light at the end of the tunnel.

Sam Bailey takes us back to that moment, the very period of time that occurred just before everything changed for the good, our goals were met, and the dream that we were about to give up on became true. She delivers in the creation of You’re So Talented and as the main character, Bea, a young artist and struggling actress fighting to stay motivated in her quest to fulfill her dreams.

“I have learned… Better an asshole than a chicken shit… I love that idea to just go in full heartedly with everything that you want to do. And if you make an asshole of yourself its better than being a coward.”Sam Bailey

Bailey has earned her stripes and built an extensive resume as an actress all over the windy city working in places like the Strawdog Theatre, ATC, and The Gift. Her writing work has been showcased in live performance clubs like The Paper Machete, BYOB Story Hour, and Guts And Glory.

Chicagoans Ashleigh Lathrob, Gabe Franken, Gabe Ruiz, Dakota Loesch, LaNissa Frederick, Behzad Dabu, Kimberly Michelle Vaughn, and Jaren Merrell also star in the series.

DB: You are a writer and an actress. When did you first know that this was something that you wanted to do with your life?

Sam Bailey: Yeah, I started acting when I was 14 doing theatre with Free Street Theater, which was a youth oriented theatre in Chicago. And its funny because at that process, you’re writing all of your work as an ensemble, but by the time I got to college I kind of left the writing part behind and just focused solely on acting. And it wasn’t until about a year and a half ago that I started writing again and really committing to focusing on that and giving it just as much energy as I do my acting career. And its funny that the minute I started doing that, every door that you’d think could just reveal itself and open, did! So yeah once I started getting good feedback and started feeling good about the writing that I’m doing I think I have no choice but to lean into that and continue doing it.

image3DB: You’re So Talented follows a girl in her mid-twenties who’s basically trying to follow her dreams and figure it all out. What was one of your biggest challenges in the past when it came to figuring out your life? And what did you learn from it?

Sam Bailey: Probably one of the bigger things I’ve had to do is take a step away from the theatre world solely. At first I didn’t think I wanted to but, it just wasn’t fulfilling me in a way that I really wanted it to do as much as writing and producing my own stuff is doing. But that’s a really difficult thing when that’s all you’ve done since you were 14 years old. So in the last decade and year, almost 12 years, I defined myself by being a theatre actor and in the last two years I’ve had to rethink that. And that’s really difficult because if you had told me three years ago that I was going to stop doing theatre I would of been like, “Uh you can go screw yourself.” You know? But now it feels like a whole other world and its hard for me to sit in that space comfortably now.

1DB: How are you similar to your character Bea? And also how are you different from her?

Sam Bailey: I’m also in my mid twenties, 25 years old. And I think Bea has less of a sense of self than I think that I have. She doesn’t really know what she wants but, I can relate to that in doses. I think Bea lives that. I think her normal at zero self is very unsure of who she is. And just being in the art community and being in Chicago (are similar). And those big other characters in the series are very big in my life as well. I think Bea is a little self destructive. I’m much more of the if I’m upset about something or depressed about something I will find another project to throw myself into. And she does that half heartedly and might also find other relationships that she throws herself into which doesn’t prove to be a great decision in the series. So yeah those are part of the bigger differences between the two of us.


Bailey is currently finishing up The Second City‘s Urban Twist show which has been showing at the theater all fall long and she’s also brainstorming ideas for the second season of You’re So Talented!

You’re So Talented will premiere on Vimeo January 2015.

Follow Sam Bailey on Twitter .

And keep up with You’re So Talented here:

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