Woman in red short-sleeved dress, with long curly brown hair, stands outside under light green foliage from trees.
Ana Silva Credit: Elias Rios

Ana Silva is the type to celebrate Groundhog Day. 

On a January morning, over Zoom, Silva recounts how she “asked off work” for the woodchuck festivities. She and her boyfriend, actor Andrew Jessop, are driving to Woodstock, where the 1993 classic Groundhog Day was filmed. Next on the list is a groundhog-themed pub crawl followed by a bags tournament. They are especially excited to meet mascot Woodstock Willie.

Wearing a Prussian blue flannel, Silva sits in her kitchen. A natural storyteller, she leans forward when she speaks like she’s telling me a secret. Her cocoa curls upstage her espresso cabinets. I can’t see much of her background, except for a large jar of coconut oil and a yellow onion perched on her gray marble counter. 

Effortlessly funny, Silva talks about her first taste of stardom—her kindergarten’s rendition of Mary, Mary, Quite Contrary. She was determined to play Mary: the lead who forgot to water the flowers. But she was cast as one of the flowers. “And that’s the story of my life,” she says.

In high school, her only representation onscreen was America Ferrera. “How fucked up that a person who looks like me is in a show titled Ugly [Betty],” Silva says. “It brainwashes you into believing there is no space for you.” 

And beyond the lack of TV representation, Silva experienced this bias firsthand offscreen. When she studied acting in Los Angeles at the American Musical and Dramatic Academy, she “didn’t fit the media standard of beauty.” One of her teachers told her she wouldn’t find work until she was 30 because she wasn’t a size two. Casting agents would tell her, “We don’t know where you belong,” because she’s Latina but doesn’t speak Spanish. “And it destroyed me,” she says. 

This April, Silva will make her debut as Sister Sophia in The Sound of Music at the Marriott Theatre in Lincolnshire, opening in previews on April 13. Rehearsals began on March 28. 

“I thought I bombed the callback,” Silva says. After forgetting the lyrics halfway through “How Do You Solve a Problem Like Maria,” and having to start over, Silva left the audition thinking, “’Well I lost this job,’” she says. Jessop drove her to the callback in the midst of a blizzard, which probably didn’t help the overall vibe. “We came home, and I cried and cried and cried, and we’re having lunch and I got the offer,” she says. 

For her fall performance in Theater Wit’s Mr. Burns, a Post-Electric Play, Silva was runner-up for the Reader’s 2021 “best stage actor.” (She lost to Carrie Coon, who is currently starring in HBO’s The Gilded Age.) After that, she took an impromptu break from performing. Despite being vaccinated and boosted, Silva caught COVID-19 and even missed seeing her family over the holidays. The last time she saw them was for her grandfather’s memorial service this past summer.

“I come from a green card marriage,” Silva says. Her father is from Brazil, and her mother, who died five years ago, “was a Jew from Long Island.” Growing up in Portland, Oregon, aka “the cool Portland,” with her parents and two siblings, Silva is the quintessential middle child. Olivia, her older sister, is a nurse who married an electrical engineer and, as a result, is “the pride of the family,” she says (only half-jokingly). 

Silva’s parents expected her to go to law school, not acting college, “which is basically clown school,” she says. It’s safe to say they weren’t happy when she pursued live theater, and it wasn’t just a phase. Especially when she moved back home shortly after college to live in her dad’s basement and work at Baskin-Robbins. “People that I went to high school [with] would come in and be like, ‘Why is the valedictorian serving me chocolate fudge?’” Silva says as she laughs.  

After dabbling in improv, Silva moved out of her dad’s basement and to Chicago where she fell in love with sketch comedy. Improv allowed the self-described “biracial deviant” to perform with a diverse community she felt safe with. “I ended up finding my family here,” Silva says. “It’s through working with them that I have felt empowered to come into my own.” 

Having the coronavirus forced Silva to get in touch with her body and ask herself, “What does it mean to take care of myself again?” Since then, she has opened an Etsy candle shop, FireandFlameCandleCo, with Jessop, who she’s been dating for six months now. 

Silva also worked as a med spa receptionist, which she describes as “low-key, a therapist service where people put things in their face to convince them that they’re now pretty when they were gorgeous before.” Earlier this month, she quit. “I know that there are people who can do this for a living and they don’t have to work at a med spa,” she says. “I’m so ready for that to happen.” 

Now a stage actor, writer, comedian, Second City teacher, and candle connoisseur, Silva uses entertainment to “create a world that you want to see.” A master improviser, she has performed with three local troupes, including Improvised Jane Austen and Baby Wants Candy, a long-running musical improvisation troupe with notable alums like Saturday Night Live’s Aidy Bryant. 

Silva was also a member of Matt Damon Improv, composed entirely of women of color. Occasionally, they would invite a white male or female to perform with them. (I recommend watching their In-Diana webseries, filmed entirely on Zoom during peak quarantine. The project won Best Web Series in the London International Web & Shorts Film Festival last year.)  

The members of Matt Damon Improv went on to pursue individual projects, but they remain best friends. Maria Konopken, a Matt Damon member, remembers when Silva joined their team. After performing with her a few times, they made it official. “It was like a proposal,” Konopken says. At a local improv festival, Matt Damon cofounder Allison Reese was handing out wristbands to members. Silva was sitting in the corner, just enjoying her Stella Artois. That’s when Reese turned to her with a wristband and popped the question, “Will you be on Matt Damon Improv?” Silva jumped out of her seat and shrieked in excitement. 

Last December, Silva celebrated her 30th birthday. In the last decade, she’s accomplished more than her teacher could fathom, including starring in a Mike’s Hard Lemonade commercial. And after taking a brief hiatus from the theater scene, she’s eager to return to the stage. 

Her father now sees why she loves it so much. “But when I told him that I got this [Reader] nomination, his answer to me was, ‘You know, I had a dream last night that you got an MBA and were working on the stock market in New York City,’” she says. While Silva was Rex Putnam High School 2010 valedictorian, she doesn’t want to be a nurse, an engineer, or worse—a finance bro. 

This May, her family is flying in to celebrate her many accomplishments, including The Sound of Music. They will also be meeting the boyfriend for the first time, but that’s a whole other story.