Acting Up: James O'Connor '98 Makes Name for Himself in Hollywood

O'Connor has performed alongside stars including Richard Gere, Bill Murray and Donnie Wahlberg

He’s been a Commie and a cop, a goon and a grieving father, a hitman and he’s been hit a few times. Welcome to the world of character actor James Andrew O’Connor ’98, a guy who growls like a grizzly bear before the camera, but chuckles like a teddy bear when you meet him in person.

“I’m a big, six-foot-five, 300-pound guy,” he says with a laugh. “I’m not going to play Bob Dylan. But I’d love to play Orson Welles, a person I get compared to all the time.”

O’Connor, who was a theatre major at Holy Cross, has built his career playing nuanced supporting characters on television shows, including “The Americans,” “Chicago P.D.,” “Gotham” and “The Blacklist,” and in movies, like “St. Vincent.” But don’t let his steely on-camera stare fool you — at home, his favorite role is playing dad to his kids, Stephanie, 3, and James, 1, with his wife and audition coach, Tammy.

“You should see me at home,” he says, chuckling. “I’m a teddy bear. I’m a mush. Sometimes I cry at car commercials.”

Theatre Roots

O’Connor grew up in the Bronx, raised by parents who constantly took him to movies and Broadway plays. His first acting gig was in high school English class, where everyone had to perform a monologue from Shakespeare. He chose Shylock’s speech from “The Merchant of Venice.”

“My father, James, rehearsed it with me, and kept quizzing me about the choices I was making with the speech,” he remembers. “In class the next day I was terrified, but I raised my hand to go first. And I nailed it. Afterward, some of my classmates said, ‘You did really good.’”

He was in a few high school plays and entered Holy Cross as an English major, joining Alternative College Theatre and acting for fun in productions of “My Fair Lady,” “Measure for Measure” and “Iolanthe,” among others.

“[Theatre] Professor Steve Vineberg told me, ‘I’d love to see more of you in class,’” O’Connor says. “And at the end my sophomore year, Professor Edward Isser [current chair of the theatre department] asked me, ‘Are you in this to have fun, or do you want to learn and grow?’”

While he thanks Vineberg, Isser and other faculty mentors for encouraging him to pursue a theatre career, it was a heart-to-heart talk with his father that finally pushed him on stage.

“I was worried about my grades and told my father over the phone that I didn’t want to be an English major. He asked, ‘If it was up to you, what would you want to do?’ I told him I’d rather study theatre. He told me to go ahead and do it. I couldn’t speak; I was floored. I asked him, ‘Why didn’t you tell me I could do that?’ and he said, ‘Because I’ve been waiting for you to tell me that.’” O’Connor pauses, then adds, “That was a very significant moment in my life.”

O’Connor with Willie Garson on the set of the USA Network TV series “White Collar.”

The Big Break

After graduation, he studied acting in New York City and auditioned for countless roles, “getting to the Actors Equity Association office by 6 a.m. sometimes,” he says. He performed in several Off-Off-Broadway productions and with the National Shakespeare Touring Company. But his big break came when he moved into an apartment in Jersey City, New Jersey, next to a couple whose daughter was a casting director for several television shows, including “Law & Order.”

“Not knowing who her parents were, I was helping them move some furniture one day, and they said they’d put in a good word for me,” he says. “So I called her and we spoke every couple months, and then she offered me a part in a show. I was a character in a hospital bed.”

In the 17 years since, O’Connor has appeared in dozens of movies and television shows, and also does voice-over work on video games. You can catch him this December as the fire chief in “The Greatest Showman,” a biopic about P.T. Barnum starring Hugh Jackman.

“We had an overnight shoot in the pouring rain, and we did several takes on a scene where I had to tackle him to prevent him from entering a burning building,” he says. “Hugh was great to work with. He always carried scratch-off lottery tickets in his pockets, and he’d hand them out to everyone.”

Though the ticket Jackman handed him wasn’t a winner, O’Connor feels he’s winning greater recognition in the film and television industry. He’s also helping others find success by coaching young actors and assisting his fellow Holy Cross alumni with their projects, including co-producing, with Brud Fogarty ’00 and Clifford Kirvan ’98, “No Alternative,” a film about mental illness, written and directed by William Dickerson ’01.

Five Questions with James O’Connor ’98

What’s the oddest exercise you’ve ever done in an acting class?

Probably being an animal. Acting exercises are supposed to break your inhibitions. Some teachers say when you’re approaching a character, pick an animal and model your character after that animal. I was always a bear – maybe I should’ve challenged myself and tried to be a lamb.

Who’s your favorite Muppet?

I keep telling my agent, “I want you to get me on ‘Sesame Street.’” He just laughs at me. [O'Connor laughs.] I’ve always liked Fozzie Bear because, like me, I was once a struggling actor and Fozzie’s a struggling comedian. But I also like Rowlf the Dog, which was Jim Henson’s favorite. Rowlf could drop one-liners and keep everything light.

O’Connor acted alongside Bill Murray in the 2014 film “St. Vincent.”

What was it like working with Bill Murray on “St. Vincent”?

Bill was a sweetheart. He was so approachable, funny and kind. He knew how to keep things upbeat. During our scenes together, he kept telling me to look at things over my shoulder. He’d say, ‘Is that a yellow-bellied warbler?’ and I’d look around, and then he’d throw me a fake punch.

What was the last movie that made you cry?

“Dead Poets Society.” I revisit that movie at least once a year. I just watched it last week, largely for Robin Williams. No other actor could make me laugh or cry with such ease. I knew if I was walking into the theatre to watch him, I'd walk away feeling better than when I walked in. In my field, I've encountered many artists battling resistance to their passion and choices. This film manages to simultaneously devastate me and inspire me. It has definitely shaped me as an artist.

Would you rather play a superhero or a supervillain?

I’d rather be superhero. When I was younger, I was drawn to darker stuff, but I’m attracted to more significant roles now. I want to have a positive influence on people. I like telling stories that make you think, inspire you and make you feel good about yourself. I want people to say, “You inspired me with your performance.” My resume is full of gangsters and thugs. (Pause.) But playing a supervillain would also be fun.

Written by Benjamin Gleisser for the Summer 2017 issue of Holy Cross Magazine.

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