Leonardo DiCaprio may have an Oscar, a career full of box-office hits, and a resume filled with iconic films, but he has a career choice he wishes he could take back. In a conversation with director Paul Thomas Anderson, DiCaprio revealed the one role he regrets turning down, and it involves a now-classic porn-star drama from the late ’90s.
Leonardo DiCaprio shares his biggest regret in Hollywood
Leonardo DiCaprio has spent decades dominating the big screen, from Titanic to Inception and The Wolf of Wall Street. He’s worked with the world’s top directors, bagged an Academy Award for The Revenant, and consistently pushed his craft. But when it comes to regrets, the actor points to one missed opportunity: Paul Thomas Anderson’s Boogie Nights.
In Esquire’s latest cover story, DiCaprio sat down with Anderson and admitted that not taking the role of Eddie Adams, aka Dirk Diggler, still stings. Anderson had him in mind after seeing The Basketball Diaries, but the shooting schedule clashed with Titanic. DiCaprio had to choose, and James Cameron’s epic won.
“My biggest regret is not doing Boogie Nights,” Leonardo DiCaprio said. “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.”
Rather than leave Anderson empty-handed, DiCaprio suggested Wahlberg, his co-star from The Basketball Diaries. The role turned out to be a career-defining moment for Wahlberg, while Boogie Nights became a cult classic.
Fast forward nearly three decades, and DiCaprio is finally teaming up with Anderson on One Battle After Another, set for release on September 26. The action drama blends high-octane chases and shootouts with an emotional father-daughter storyline. DiCaprio plays Bob Ferguson, a washed-up revolutionary trying to protect his teenage daughter, Willa, played by Chase Infiniti.
For DiCaprio, this project is more than a long-awaited collaboration as it’s the fulfillment of a creative itch that’s been there for years. “I’ve been wanting to work with you—Paul—for something like twenty years now,” DiCaprio told Anderson. “It’s about the disconnection between generations… We think we understand it, but we don’t.”
