Interview: Dually talented Sarah Dooley is self-made, self-making

Sarah Dooley

Sarah Dooley, courtesy: James Underwood.

Comedian, musician and author Sarah Dooley, a creative powerhouse, might seem like she’s resting comfortably at the top of her game. But even after the release of her second album, Is This Heartbreak? Dooley has never stopped moving, making and re-making herself.

“I started writing music in high school,” Dooley said in a recent video call. “But it wasn’t until I started dating comedians and going to their shows in New York that I was, like, ‘Oh, I can do this.’ The dream is to write a movie-musical, or a musical show that would combine the two things I like to do. But other than that, I just like to do both.”

Dooley is self-taught in both music and comedy, other than years of piano lessons. She never thought she’d be a self-made comedian.

“I did the improv show at my high school, and it was like the worst night of my whole life,” she said. “I was like, ‘I can never show my face again.’” 

Fortunately, bombing in her high school’s “Dating Game” production didn’t deter her from pursuing comedy, and her 2011 web series “And Sarah” was covered by the New York Times. Her 2019 parody book, “Are You My Uber?” received substantial internet acclaim. 

The making of Dooley’s music career has been just as audacious as her comedy. After some success at Barnard College, which she attended, Dooley made a name for herself playing gigs around New York City. Dooley’s 2014 debut album, Stupid Things, eventually hit No. 16 on the iTunes pop chart.​  

In 2018, she reached national popularity with her cover of Ira and George Gershwin’s standard “But Not For Me” was featured on CBS show “The Good Fight.” She released her latest album, Is This Heartbreak? in October. As she always does, Dooley made her virtual release party work. 

“It ended up being really special, because so many more people could come from different parts of the country,” Dooley said. “It was also like me screaming in my apartment to no one. I would finish a song and just be in my kitchen.”

Dooley said she wrote the album about past relationships, but life ended up imitating art in the most ironic of ways.

“As I was getting ready to release it, my current relationship ended,” she said. “It was so bizarre to be singing these songs that I wrote for myself to get over breakups in my early twenties, and they still speak to me now.”

Is This Heartbreak? ended up being an amalgamation of songs that she described as “a museum of heartbreak,” showing her listeners vignettes of her life in song throughout the years. 

Dooley’s latest transition has been her recent move to L.A. from New York. She gushed about the her balcony view looking up to the Hollywood sign.

“It’s my dreams. I moved to LA and it’s suddenly, like, deer are helping me get dressed in the morning,” she said. “This is a magical place. I don’t know if I’ll get ever over it.”

Through social media, Dooley has been able to combine her love of music and talent for comedy in a grassroots way. She’s also learned how much work growing your own following takes. She liked to create slowly. Tik Tok doesn’t really allow for that. Dooley churns out posts with accents and impressions to fan-requested cover songs. Her “Weekly Bedroom Concert” series proved to be a hit with followers. Next, she wants to record and produce some of those covers..

Then there’s Spotify, which she hadn’t much paid attention to until she needed people to stream her songs.

“And it feels so annoying to ask people. It feels so impersonal. But it’s make or break,” she said.

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