Three Decades In, Leonardo DiCaprio Has Worked With Just One Female Director — And It Flopped

Leonardo DiCaprio just reminded everyone how long it has been since he worked with a woman behind the camera. Short answer: three decades. After his latest 'Actors on Actors' chat, fans started doing the math and, yeah, it has been since the mid-90s. Let’s unpack how we got here, what people are mad about, and why this conversation keeps coming back.

How the question came up

During his sit-down with Jennifer Lawrence, DiCaprio was asked the classic 'white whale' question: which director is still on his wish list. He name-checked the usual heavy hitters — Damien Chazelle, Michael Mann — and talked about how close he once came to teaming with Paul Thomas Anderson.

"There’s a lot of great directors out there. Damien Chazelle is very talented. Michael Mann’s amazing, I’ve always wanted to work with him. I don’t have one specifically, Paul [Thomas Anderson] was always somebody generationally that I really looked up to. We almost did 'Boogie Nights' together, and then I got to watch his entire career progress over the last 25 years and see this incredible visionary."

It was a perfectly fine answer. But the internet zeroed in on what he didn’t say: any female directors. On Dec 17, 2025, writer Emmy Potter pointed out that Leo hasn’t made a movie with a woman director in 30 years. Others quickly chimed in with names they’d love to see him team with, like Lynne Ramsay ('Die My Love') or Kelly Reichardt ('The Mastermind').

Yes, he has done it — twice, early on

To be fair, DiCaprio did work with women at the very start of his career. Kristine Peterson directed him in 'Critters 3' (1991). And in 1995, he took a big swing with Agnieszka Holland’s erotic historical drama 'Total Eclipse,' playing 19th-century French poet Arthur Rimbaud.

That movie? Complicated legacy. Critics mostly shrugged at the film but singled out DiCaprio’s performance as bold and electric. Holland herself later said he carried himself like a seasoned pro, even as a teenager:

"Probably Leonardo was still 19, but not for one moment did I have the impression I was dealing with a newcomer. He was one of the most mature actors I’ve ever worked with."

Commercially, though, 'Total Eclipse' face-planted. And there’s some confusing labeling floating around — you might see 1991 attached to the title in a few places — but the movie was released in 1995. Here’s the snapshot everyone keeps citing:

• Title: Total Eclipse (1995)
• Director: Agnieszka Holland
• Production budget: $8 million
• Box office: $340,139
• Rotten Tomatoes: 24%
• IMDb: 6.4/10

If that one flop is the reason he never tried another woman-led project, that’d be a pretty thin barometer — but we don’t actually know why it hasn’t happened again. It might be taste, timing, the projects he chooses, or just inertia at this stage of his career.

The criticism is not new

Back in 2019, critic Guy Lodge pushed back on a glowing Hollywood Reporter piece that praised DiCaprio for avoiding capes, lightsabers, and sequels. Lodge’s take: Leo’s picks are prestige and high quality, sure, but not exactly daring, and almost exclusively with established male auteurs. He also flagged that Leo hadn’t worked with a woman director since 1995 — and said that’s not a trivial detail. Another critic, Kayleigh Donaldson, backed that up, calling DiCaprio the safest major star in town and wishing he’d take on riskier, more dangerous roles — and, by extension, riskier collaborators.

So where does he go from here?

Fans clearly want to see DiCaprio stretch — not just in what roles he takes, but who he lets steer the ship. The Lynne Ramsay and Kelly Reichardt suggestions are strong for a reason: both are meticulous, uncompromising filmmakers who would probably pull something new out of him. If Leo truly wants a fresh chapter, pairing his clout with a woman director feels like the easiest big swing he could take.

Who would you want to see him team up with? Drop your picks — the more unexpected, the better.