Two Oscar winners, more than thirty years in the same business, and not one shared credit between them. A dinner in Santa Monica and a bankrupt startup are as close as the two have come.
Three men sat down to eat at Giorgio Baldi, an Italian restaurant in Santa Monica, on a Thursday night in December 2024. Robert De Niro and Robert Downey Jr came with their wives and walked past the photographers outside without covering their faces. Leonardo DiCaprio arrived separately, wearing the hat and mask he tends to wear in public. TMZ, which reported the dinner, said the three had arranged to meet rather than run into one another.
None of them has said what it was about.
Table of Contents
Have DiCaprio and Downey ever been in a film together?
No. Neither actor has appeared in a film with the other in any capacity, across careers that have run alongside each other for more than three decades. There is no record of a friendship, and neither man has discussed the other in an interview. What links them comes down to two Academy Awards ceremonies, one collapsed company, and that table in Santa Monica.
Two Oscar nights, two years apart
The 2024 ceremony is the one worth starting with, because DiCaprio was not there.
On 10 March 2024, Downey won best supporting actor for playing Lewis Strauss in Oppenheimer. It was his first Oscar, on his third nomination in a career that began when he was a child. The man he beat was Robert De Niro, nominated for Killers of the Flower Moon.
DiCaprio starred in that film. He was not nominated for it, and the picture lost all ten of the awards it was up for, including best picture. He skipped the ceremony.
De Niro is the thread here. He and DiCaprio first worked together in 1993, when a nineteen year old DiCaprio played his stepson in This Boy’s Life, and again three decades later on Killers of the Flower Moon. Nine months after losing to Downey, De Niro was at that dinner table with both of them.
Two years on, at the 98th Academy Awards on 15 March 2026, DiCaprio finally got the nomination that had passed him by. He was up for best actor for One Battle After Another, Paul Thomas Anderson’s film in which he plays a former revolutionary searching for his missing daughter. He lost to Michael B. Jordan for Sinners.
Downey was on the same stage. He came out with Chris Evans, his old Avengers co-star, to present the writing awards, and handed the adapted screenplay Oscar to Anderson for the same film that had put DiCaprio in the running. One Battle After Another took six awards that night, including best picture and best director. Its leading man got none of them.
A failed green bank put both their names on the same filings
Away from film, the two turn up in the same place for a less flattering reason.
Securities and Exchange Commission filings list DiCaprio and Downey among the investors in Aspiration, a Los Angeles company that sold itself as an environmentally minded alternative to conventional banking, with fossil fuel free funds and tree planting linked to customer spending. Orlando Bloom, Cindy Crawford and the NBA coach Doc Rivers also put money in. The company reached a valuation of $2.3 billion in 2021, and Clippers owner Steve Ballmer invested personally, making Aspiration a team partner.
It filed for bankruptcy in 2025. A co-founder pleaded guilty to wire fraud.
The collapse became a sports story that September, when the journalist Pablo Torre published internal documents suggesting the Clippers had used a $28 million Aspiration endorsement deal to pay Kawhi Leonard without requiring much promotional work from him, allegedly to get around the NBA salary cap. According to that reporting, DiCaprio and Downey, who did make public appearances for the company, were paid a fraction of what Leonard received. The NBA opened an investigation. Neither actor has been accused of any wrongdoing.
The investment fits what both have done with their money elsewhere. DiCaprio has funded conservation work through the group Re:wild since 2021, after closing the foundation he set up in 1998. Downey started FootPrint Coalition in 2019 and added a venture arm two years later, backing climate technology companies including the nuclear fusion firm Commonwealth Fusion Systems.
The two careers, side by side
| Leonardo DiCaprio | Robert Downey Jr | |
|---|---|---|
| Age | 51 | 61 |
| First Oscar nomination | 1994, What’s Eating Gilbert Grape | 1993, Chaplin |
| Acting nominations | 7 | 3 |
| Oscar win | The Revenant, 2016 | Oppenheimer, 2024 |
| Franchise work | None | Marvel, 2008 to 2019, and again from 2026 |
| Estimated net worth | About $300 million | About $300 million |
Net worth figures come from Celebrity Net Worth and are estimates rather than confirmed accounts.
The similarity in those last two rows is the odd part, because almost nothing about how the two men got there matches.
DiCaprio has never signed on for a sequel or a superhero film. After Titanic made him the most photographed actor of the late 1990s, he narrowed rather than widened, working repeatedly with the same handful of directors. Six films with Martin Scorsese since Gangs of New York in 2002, including The Wolf of Wall Street. Long gaps between projects.
Downey had no such luxury. Years of addiction and arrests had left studios unwilling to insure him, and in 2008 he took $500,000 to play Tony Stark in Iron Man, far below what an actor with an Oscar nomination behind him would normally command. He stayed with Marvel for more than a decade, ran the Sherlock Holmes films alongside it, and by Celebrity Net Worth’s estimate earned between $500 million and $600 million from the Marvel work alone.
What each is doing now
Both spent this year on something they had previously avoided.
DiCaprio finished filming What Happens at Night in the spring, a horror film adapted from Peter Cameron’s novel, with Jennifer Lawrence playing his wife. It is his seventh feature with Scorsese and his first real move into the genre. He missed the Screen Actors Guild ceremony on 1 March, despite being nominated, because he was on set in Europe.
Downey returns on 18 December as Doctor Doom in Avengers: Doomsday, playing the villain in the series that rebuilt his career as its hero. Reports put his fee for that film and its 2027 sequel, Avengers: Secret Wars, above $100 million.
Neither schedule leaves an opening. Downey is committed to Marvel into 2027. DiCaprio begins shooting Midnight Vendetta, another Scorsese picture, this December, with a second project about the Hawaiian underworld to follow. Thirty years in, the closest the two have come to working on the same thing was a company that went under.
