Benicio del Toro and Sean Penn have appeared together in 6 films between 1991 and 2025, with a combined box office of $303.1 million. Every shared film with year, roles and gross, plus who else each works with most.
| Year | Film | Box office |
|---|---|---|
| 1991 | The Indian Runner | $191,125 |
| 2001 | The Pledge (film) | $29.4 million |
| 2003 | 21 Grams | $60.4 million |
| 2006 | Buy the Ticket, Take the Ride: Hunter S. Thompson on Film | |
| 2025 | Battle | |
| 2025 | One Battle After Another | $213.1 million |
Benicio del Toro also often with: Chris Penn (3), Christopher Walken (3), D. W. Moffett (3), Dennis Hopper (3), Don Cheadle (3)
Sean Penn also often with: Robin Wright (9), Eileen Ryan (8), Catherine Keener (5), R. D. Call (5), Harry Dean Stanton (4)