Leonardo DiCaprio Names ‘Boogie Nights’ as His Biggest Career Regret in Candid Interview

The glow of an Oscar statuette and decades of critical acclaim haven’t erased one lingering pang of regret for Leonardo DiCaprio. In a revealing conversation with director Paul Thomas Anderson for Esquire magazine (August 2025), the legendary actor confessed that passing on Anderson’s 1997 masterpiece Boogie Nights remains his most profound career “what if.”

DiCaprio’s Frank Admission About the Role That Got Away

Sitting across from the very filmmaker who offered him the career-defining role, DiCaprio didn’t hesitate when Anderson asked about regrets: “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 now. When I finally saw it, I knew it was a masterpiece.”

The role of Dirk Diggler—a rising star in the adult film industry’s gritty 1970s heyday—ultimately went to Mark Wahlberg after DiCaprio declined. Why? The actor had already committed to a little-known project called Titanic. Anderson had sought DiCaprio after being captivated by his raw performance in The Basketball Diaries, but scheduling clashes made it impossible. In a twist of Hollywood fate, DiCaprio personally recommended Wahlberg, his Basketball Diaries co-star, for the part—a decision that launched Wahlberg into superstardom.

The Titanic Trade-Off That Shaped Cinematic History

While Boogie Nights became an instant cultural landmark, DiCaprio’s choice to board Titanic cemented his own status as a global icon. The 1997 epic directed by James Cameron remains one of history’s highest-grossing films. Yet DiCaprio’s admiration for Anderson’s work is undeniable. He later collaborated with the director on the upcoming film One Battle After Another, proving their artistic bond endured despite the missed opportunity decades earlier.

The Scorsese Film DiCaprio Can’t Stop Rewatching

When Anderson asked which of his own films he revisits, DiCaprio surprised by naming not The Departed or The Revenant, but Martin Scorsese’s 2004 biopic The Aviator: “I rarely watch my films, but I’ve seen The Aviator more than others. At thirty, it was the first time I felt implicitly part of the production, not just an actor. I’d carried Howard Hughes’ biography for a decade. Working with Marty [Scorsese], I became a true collaborator—that pride never faded.” The role earned DiCaprio his second Oscar nomination, a partnership that would yield six Scorsese collaborations to date.

DiCaprio’s confession reveals how even icons ponder alternate paths—his reverence for Boogie Nights underscores its enduring impact, while The Aviator represents his evolution into Hollywood royalty. For fans, it’s a rare glimpse behind the curtain of cinematic legacy. Stream both classics tonight and decide: Did fate get it right?

Must Know

Why did DiCaprio really reject Boogie Nights?
DiCaprio had already signed for Titanic when Paul Thomas Anderson offered him the lead. Scheduling conflicts made both roles impossible. He revealed this in his 2025 Esquire interview with Anderson, calling it his only major career regret.

How did Mark Wahlberg get cast in Boogie Nights?
DiCaprio personally recommended Wahlberg to Anderson after they co-starred in 1995’s The Basketball Diaries. Wahlberg’s transformative performance earned him his first Golden Globe nomination and catapulted his film career.

What makes The Aviator special to DiCaprio?
It marked his first deep creative partnership with Scorsese beyond acting. DiCaprio helped develop the Howard Hughes biopic for years, calling it a “key part of growing up in the industry” during his Esquire interview.

Did DiCaprio ever work with Paul Thomas Anderson?
Yes! Their long-delayed collaboration finally happened with One Battle After Another, currently in post-production and slated for a 2026 release.

Has DiCaprio won an Oscar?
Yes, he won Best Actor for 2015’s The Revenant. He’s been nominated seven times total, including for The Aviator and Killers of the Flower Moon.