Leonardo DiCaprio's Biggest Hollywood Regret Is Missing Out On This Classic 1997 Movie

Not every actor can afford to be picky about the roles they end up taking. It's a brutal industry to be selective in. But if you see an upcoming film that stars an actor like Leonardo DiCaprio, that means he truly believes in the project. The teen heartthrob turned Academy Award-winning actor boasts quite the filmography having worked with such celebrated filmmakers as James Cameron ("Titanic"), Christopher Nolan ("Inception"), Steven Spielberg ("Catch Me If You Can"), and Sam Raimi ("The Quick and the Dead"). Working with any one of those names would give you some boost of credibility, but the fact that he's also fostered a working relationship with the legendary Martin Scorsese across six (soon to be seven with "Devil in the White City") films in two decades is a real feather in his cap. And now DiCaprio's next big role comes to us courtesy of one of our greatest working filmmakers in Paul Thomas Anderson.

Anderson's filmography is just one heavy hitter masterpiece after the other, including "Magnolia," "Punch-Drunk Love," and "The Master." He's a generational talent whose work demonstrates his near flawless ability to secure some of the best actors in the game and capture them to perfection, à la Daniel Day-Lewis in "There Will Be Blood" and "Phantom Thread." It seems pretty strange that Anderson hadn't already worked with DiCaprio before, given that they seem like a natural fit. Nevertheless, it's pretty exciting that these two artists are finally collaborating with "One Battle After Another."

In the anticipated action crime thriller, DiCaprio plays Bob Ferguson, a burned out revolutionary figure who ends up falling back into his old habits when his teenage daughter Willa (Chase Infiniti) finds herself wrapped up in a terrible predicament. Warner Bros. may not seem to have any idea of how to market this movie to casual moviegoing audiences, but for my money, DiCaprio working alongside the likes of Regina Hall and Benicio del Toro in a PTA picture says everything I need to know about being there opening night. While it certainly feels like a gift for Anderson and DiCaprio working together at this point in time, their talents could have collided a lot sooner.

In a 2025 Esquire interview, Anderson asked DiCaprio if he had any lingering regrets, to which the "Once Upon a Time In Hollywood" actor had only one — not saying yes to the lead role in "Boogie Nights:"

"I'll say it even though you're here: My biggest regret is not doing 'Boogie Nights.' It was a profound movie of my generation. I can't imagine anyone but Mark [Wahlberg] in it. When I finally got to see that movie, I just thought it was a masterpiece. It's ironic that you're the person asking that question, but it's true."

On the DVD commentary for "Boogie Nights," Anderson talks about how the decision to cast the high school dropout turned heavily-endowed porn star Dirk Diggler came down to a decision between DiCaprio and Mark Wahlberg after having been impressed by their work in 1995's "The Basketball Diaries" (via Film School Rejects). DiCaprio is such a committed actor that he probably would have given a great performance alongside the likes of Philip Seymour Hoffman, Julianne Moore, and a scene-stealing Alfred Molina, but Wahlberg fits Diggler like a glove, with the role playing to his strengths as an actor. He effortlessly transforms from a youthful optimist allured by the prosperity of fame to an industry veteran trapped in a sleazy cycle that chews him up, spits him out, and welcomes him back as a changed person.

In the late '90s, Anderson and DiCaprio were both notable 20-somethings taking big swings that ultimately sent them on the trajectory of the career paths they have now, albeit in different roles within the film industry. There's an irony to Anderson believing that DiCaprio didn't have any regrets over deciding to work with Cameron instead, only for him to reveal the opposite right at the top of their interview. I supposed it's better late than never to correct a pairing nearly three decades in the making.

"Boogie Nights" is currently streaming on Paramount+.