Years before she embarked on career as a stand-up comic, Jessica Michelle Singleton was already using humor and improvisation to win over crowds.
When her family arrived in Alaska from Mississippi, Singleton immediately started playing the role of "the new kid."
On the verge of entering the often-awkward teenage years, she struggled to fit in.
"I was a weird kid and kept to myself," she said. "I was a loner. I was picked on and bullied. I don't want to say rightfully so, but I was really weird. Instead of keeping my head down, I would fire back or make fun of myself. Halfway through high school, I became friends with a lot of people. I stopped trying to hold in my thoughts. People were all of a sudden, 'She's funny. She's not a creepy, weird person.' "
By the time she graduated from high school at Service High School, she was active in sports and named homecoming queen -- and, of course, class clown.
"I stopped trying to be something I wasn't," Singleton said.
Singleton is returning home to record her first live comedy album during a pair of shows Friday at Chilkoot Charlie's.
Singleton's unvarnished portrayal of her life -- and the peculiar way it intertwines with the lives of rest of the world's populace -- has been the comedic trademark of her young career.
It's a two-year professional stint that has already seen some notable successes. Singleton has performed on Comedy Central and CBS and has been featured on Sirius XM's Raw Dog comedy channel.
After gaining confidence throughout her high school years, Singleton had visions of performing but didn't actively pursue it until her senior year of college.
"My second-to-last semester of college, I finally looked up an open mic," she said.
She hurriedly penned her first-ever comedy act and tried it out. Little did she know, the open mic also came with a unique opportunity.
"The open mic was also a contest to get into the finals of Florida's Funniest Person," she said. "I had an amazing first set."
Organizers were wowed by Singleton's set and put her in the finals, but wanted her to clean up some of the more explicit parts of the act. But sanitizing the bit made it benign and boring.
"I took clean as Disney clean," she said. "I said to myself, 'It's not that funny but it's clean.' Of course I bombed. It was harsh but I was still like, 'This is what I want to do.' It's like a drug."
Topically, Singleton said her comedy has evolved from sex-tinged observational humor to tackling broader issues she has encountered.
"I didn't have a great upbringing," she said. "I'm talking more about that and real-life things, struggling with depression and having abandonment issues. I write about depression because it's something I struggle with, but I hope it will help other people because it's not something people are comfortable with."
She's relocated to Los Angeles, where she's been working steadily and has organized, produced and co-headlined a couple of national tours. One of her biggest gigs was an invitation to be the first English-speaking performer at the Montreux Comedy Festival in Switzerland.
"I think a lot of comedians, it takes a few years," she said. "The voice I'm at now, five years from now, it'll be more firm and more clear."
Singleton has taken cues from a wide variety of comic influences -- from George Carlin to Ellen Degeneres to Robin Williams -- and even Eric Cartman.
"People probably think I had a horrible mother because I was an 8-year-old watching 'South Park,' asking, 'Mom, what's a dildo?' " she said.
The decision to record a live album is in part to get more of her material out to the masses, even though comedy albums in the digital age aren't quite what they were during the stand-up boom of the 1970s and '80s.
"I don't anticipate a lot of physical sales," she said. "You have the option of the digital download. I don't plan to make money, it's a way of getting out there."
Increasingly, comics are turning to the Internet -- with Web series and YouTube videos to grab viewers.
"That's a big outlet," she said. "It seems silly to me but the younger generation is all on YouTube."
Singleton said the market for female comics is on the rise with the success of acts like Amy Schumer, who has garnered big audiences with her sketch comedy series and recent film "Trainwreck."
"It's a great time to be a female in comedy," Singleton said. "I think (Schumer) is really funny. There are a lot of female comics who are just as funny in different ways. It's a big thing now. (Entertainment executives) are looking for the next Amy Schumer. Any woman succeeding in comedy is good for other women. It reaffirms the fact that women are funny and that people are tuning in and want to see these women."
Singleton said she's received good feedback from other major comedians. "Tater Salad" architect Ron White enjoyed a recent Las Vegas performance and major touring comedian Brian Regan implored her to continue on her current track.
"He said, 'I think you're really honest and vulnerable and that's really brave, and a lot of people are too scared to do that,' " she said. "I want to talk about real things and make a point, but make people laugh."
Singleton isn't just in town to record the album -- she timed her trip with her 10th high school reunion and hopes to see friends and family in the audience Friday.
"I'm super excited for the record," she said. "I'm hoping everyone can come out and have a good laugh with me -- or at me."
Jessica Michelle Singleton
When: 7 and 9 p.m. Friday, July 24
Where: Chilkoot Charlie's
Tickets: $10 at the door, koots.com or brownpapertickets.com