Simon Rex Says He ‘Bombed’ His Good Will Hunting Audition So Bad, Matt Damon Started ‘Laughing’ (Exclusive)

Simon Rex is opening up about how a professional failing led to a very successful career in Hollywood.

The 51-year-old actor spoke exclusively to PEOPLE while attending a special screening of his new movie, Americana, at the Desert 5 Spot in Hollywood, Calif.

During the conversation, he reflects on his path from an MTV video jockey to an actor appearing in projects alongside the likes of Sydney Sweeney. Interestingly, he says that his acting career took off after a horrible audition that left Matt Damon “laughing” at him.

The movie in question was 1997’s Good Will Hunting, which won two Oscars and starred the likes of Damon, Robin Williams and Ben Affleck.

“It is funny because I started off as a VJ announcing videos in the ’90s, and that’s why I’m an actor,” Rex reflects, noting that director Gus Van Sant “saw me on MTV and he goes, ‘I want that guy to read for my movie, Good Will Hunting.’ ”

He continues, “So I auditioned for Good Will Hunting and I bombed the audition and he said, ‘You’re not ready, but you should go to acting school.’ And now here we are.”

Asked how the audition went awry, Rex explains, “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.”

After getting a bit more experience, Rex went on to land roles in projects such as What I Like About You, the Scary Movie franchise, Red Rocket, Blink Twice and, most recently, Americana, which premieres on Aug. 15.

According to a synopsis of the film, Rex plays a “Western antiquities dealer” who is one of “a gallery of dynamic characters clash[ing] over the possession of a rare Native American artifact.”

“After the artifact falls onto the black market, a shy waitress with big dreams (Sweeney) teams up with a lovelorn military veteran (Paul Walter Hauser) to gain possession of it, putting them in the crosshairs of a ruthless criminal (Eric Dane) working on behalf of a Western antiquities dealer (Rex),” the synopsis continues. “Bloodshed ensues when others join the battle, including the leader of an Indigenous group (Zahn McClarnon) and a desperate woman fleeing her mysterious past (Halsey).”

Speaking about his current costars, Rex notes that the group has gotten quite friendly.

“Sydney has me go to her private workout classes with her,” he tells PEOPLE, adding that she “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 also appeared in the music video for Halsey’s 2024 single “Lucky.”

Rex notes that things have come full circle, as appearing in music videos mirrors his earliest days working with MTV as a VJ.

“But it’s definitely funny because I’ve done a few music videos. I did a Pharrell music video. I did a few over the years,” he says.

The actor also launched a music career, rapping under the artist name Dirt Nasty, back in the 2000s. However, he tells PEOPLE that he is unlikely to resurrect the alter ego anytime soon.

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“Probably not, but I still as a hobby, still like to make music as a hobby, not a career. Yeah. I still will make music for my friends, but I’m just don’t want to be rapping anymore. I’m 51 years old. This is what I should be doing,” he says.

Rex attended the screening with girlfriend Maia Kai, who had been kept in the dark about the project.

“I haven’t told her anything,” he tells PEOPLE. “It’s always better to see a movie not knowing anything. That’s always the best way to see a movie.”