Though we know him as the controversial Jamie Dutton, Wes Bentley had been building his resume long before Yellowstone came around for him. Born and raised in Arkansas, the 45-year-old actor took a liking to acting and performing at a young age, growing up to two Methodist preachers who did their own sort of performing in the days of his youth.

From performing improv with his brothers to landing a spot at Juilliard, Bentley would ditch the prestigious acting school to put his skills into practice, and that’s exactly what he did in 1999’s American Beauty, a film that took home the Academy Award for Best Picture.

Bentley’s early fame was quick, but the actor was sticking to doing things on his own terms — he even turned down the possibility of playing Spider-Man way back when. His justification? “I didn’t want to do it, because at the time, comic-book movies weren’t appealing,” he told Men’s Health. “They were not cool.” Furthermore, he explained that he had no desire to be a teen heartthrob or action star.

Despite his early opportunities for a successful career, the young actor would stray down a path fueled by addiction before getting sober and ultimately rebuilding what he had at the beginning of his career.

Part of this rebuilding was his 2012 role of Seneca Crane in The Hunger Games, his 2014 role in Interstellar, recurring roles in American Horror Story and plenty more before taking on perhaps his most celebrated role as Jamie Dutton.

Wes Bentley in ‘Yellowstone’

Bentley’s character of Jamie Dutton is a complicated one. When the series begins, he’s something like an obedient dog, doing whatever possible to earn his father’s approval. However, as time goes on, the layers are peeled back and we learn that there’s more to his character that meets the eye.

Not only is it revealed that Jamie is not John’s biological son, but we also come to discover the reason for Beth’s extreme animosity toward his character. In addition to this, as there comes to be a larger and larger wedge between he and the family he was raised believing was his own, his loyalty is tested continuously — tests in which he repeatedly fails.

“I try not to judge my characters, but it’s been enough years that it’s hard not to at this point,” Bentley told The Hollywood Reporter in 2023. “It’s very hard to play him. And at the same time, I love it. I’m going to miss the challenge. Every single scene is literally the hardest scene I’ve ever had to do. Or it’s bringing in a new challenge. If the next thing is not the same challenge, I’m definitely going to miss it.”