Actor Richard Esteras will tell you, he has always played a certain type. At over 6 feet tall and festooned with tattoos, the long-haired, deep-voiced, barrel-chested actor of Mexican heritage has a look that has led to a run of roles he describes as the proverbial “mean guy or bad guy.”
But these aren’t the only roles Esteras, who has a complicated past (more on that later), has in his sights.
Four years ago, Esteras’ acting trajectory changed when he was cast in a recurring role as Manny, a restaurant dishwasher, on the hit Hulu series “The Bear.”
And now, while the show is on hiatus, Esteras takes on his biggest acting challenge to date — the role of Waffles in Anton Chekhov’s classic drama “Uncle Vanya.”
“I enjoy playing different roles, and I don’t get many offers like this,” Esteras says. “When an opportunity like this comes along, I’m happy take it on. I’m just absorbing the whole process.”
Director Spencer Huffman helms an adaptation of “Uncle Vanya” written by Pulitzer Prize-winning playwright Annie Baker (“The Flick,” “Circle Mirror Transformation”), which brings colloquial language to Chekhov’s story of resentment and yearning.
As he did with last year’s sold out production of Caryl Churchill’s “Far Away,” Huffman stages the play inside Servi-Sure, a factory on the city’s North Side. The nine-member cast also includes veteran actors Lawrence Grimm in the title role, Rae Gray as Yelena and Jonathan Weir as The Professor.
Unlike the other actors in the cast, Esteras, who has acted in only two plays (“Hell Cab” and “Santos & Santos,” both in Chicago), had no familiarity with “Uncle Vanya” but says he was “up for the challenge.”
Waffles is a mild-mannered, impoverished landowner who wants people to get along. And in Chekhov’s play, filled with themes of regret and the search for meaning in life, that’s an uphill battle.
“Richard brings an apparent contradiction to the role, which I think is fantastic,” Huffman says. “It’s this great opportunity as an actor to play against his type so the audience will discover another side of his talent.”
Esteras’ path to a acting began later in life; his early years had him on a completely different trajectory.
Born in El Paso, Texas, Esteras’ was a child when his parents, lured by work in the steel mills, moved the family to Gary, Indiana. As a teenager, he admits he wasn’t “a great kid.”
“I was in and out of trouble, and I started hanging around with drug dealers and all that,” Esteras, 56, admits. “And in my 20s, I got into a situation where I was facing time in prison. I ended up incarcerated for four years.”
Upon his release and in an attempt to start over, Esteras moved to Arizona where he “tried to live a normal life and stay out of the spotlight.” He worked a series of everyday jobs before returning to Gary in 2009.
Acting had been something he always fantasized about, but he had no idea how to make it a reality.
“I was 40 by this time and figured I wasn’t going into acting. But people were always commenting on my voice, so I decided to try voiceover work.”
He took classes at Acting Studio Chicago, where instructors said he had a good voice but also “an interesting look” and they recommended he take improv and acting classes. What followed was a year’s worth of additional classes at The Second City and the Acting Studio.
About those improv classes: “I didn’t know anything about improv, and, at first, I didn’t know what was going on,” he says with a laugh. “Most of the students were in their 20s and I was in my 40s. It was so much fun.”
Yet there was still a learning curve to conquer. Auditions, head shots, signing with an agent were still foreign to him.
“I took a not-great selfie and went to Walgreens and made some 8x10s,” Esteras recalls. “I heard a photographer was having a contest for the worst head shot. I entered my photo and won free head shots and began going on auditions.”
Esteras landed roles in “South Side,” “Shameless” and “Chicago P.D.” and signed with Gray Talent Group. In 2015 he was cast in his first film role, “Hood,” an urban re-telling of the Robin Hood myth set in Chicago.
“I never thought acting would happen for me. I thought my past would get in the way, but people encouraged me, saying Danny Trejo has tattoos and is an ex-felon and he’s had success. And then years later here I am in a film with Danny Trejo (2024’s ‘Seven Cemeteries’).”
As for “The Bear,” Esteras says he loves everything about being a part of the family vibe of the ensemble. (A highlight was attending the Screen Actors Guild awards in early 2024 when the show won best ensemble in a comedy series.)
“The cast and crew are a wonderful group to be around,” he says. “Even though the show has blown up, everyone has stayed grounded and focused.”
Now with the addition of “Uncle Vanya” on his resume, Esteras hopes a variety of roles will continue to come his way.
“Everything I’m going through now is a learning experience. I’ve never stopped learning, as far as acting goes. I just love trying to figure out how I want to play a character and giving it all I’ve got. It’s a challenging and fun journey.”