Simon Rex Says Embarrassing Moment with Matt Damon Helped Launch His Career

An awkward audition with Matt Damon became the unexpected launchpad for Simon Rex’s acting career. Now, the actor is opening up about the misstep that helped shape his path in Hollywood.

At a special screening of his upcoming film Americana, the 51-year-old actor exclusively  revealed to People that his first audition — for 1997’s Oscar-winning Good Will Hunting — went so poorly that it had Matt Damon “laughing” in the room.

“It is funny because I started off as a VJ announcing videos in the ’90s, and that’s why I’m an actor,” Rex said, explaining that director Gus Van Sant noticed him on MTV and invited him to read for the film. “I auditioned for Good Will Hunting and I bombed the audition. He said, ‘You’re not ready, but you should go to acting school.’ And now here we are.”

Rex said his lack of experience was obvious. “I was reading the lines like a robot because I had never acted before. And Matt Damon was laughing at me as I’m reading the lines like this,” he shared.

Rex Takes on Western Antiquities Dealer Role in Americana

Following Van Sant’s advice, Rex attended acting school and went on to build a varied career with roles in sitcoms, comedies, and indie dramas. His latest role is in “Americana”, which hits theaters in August. He plays a Western antiquities dealer caught in a dangerous race for a rare Native American artifact, starring alongside Sydney Sweeney, Paul Walter Hauser, Eric Dane, Zahn McClarnon, and Halsey.

Rex said he has grown close to his co-stars, even joining Sweeney for private workout sessions. “Sydney rents out a gym so no one bothers her and then she invites me and I go… we get to have a private workout, which is fun,” he said. While he still makes music as a hobby under his former rap name Dirt Nasty, he added that acting remains his main focus.

Rex to Star in Campy Horror Comedy ‘Halloween Store‘

In addition to “Americana”, Rex has signed on to star in the upcoming horror comedy “Halloween Store” alongside Natalie Lind, according to Variety. The film follows a group of people trapped inside a costume shop on Halloween night while a mysterious killer is on the loose.

The project is directed by Shane Dax Taylor and executive produced by “Saturday Night Live” star Kenan Thompson and John Ryan Jr. through their Artists for Artists banner. Additional executive producers include Steven Schneider, Taylor, John Lind, and Bradley Sloan. 

Reflecting on his focus moving forward, Rex told People, “I’m 51 years old. This is what I should be doing.”