Sean Penn and Michael Wincott have appeared together in 4 films between 2000 and 2018, with a combined box office of $19.6 million. Every shared film with year, roles and gross, plus who else each works with most.
| Year | Film | Box office |
|---|---|---|
| 2000 | Before Night Falls | $8.5 million |
| 2004 | The Assassination of Richard Nixon | $4.4 million |
| 2008 | What Just Happened | $6.7 million |
| 2018 | What Just Happened |
Sean Penn also often with: Robin Wright (9), Eileen Ryan (8), Benicio del Toro (6), Catherine Keener (5), R. D. Call (5)
Michael Wincott also often with: Christopher Adamson (3), John Turturro (3), Alessandra Daniele (2), Angela Bassett (2), Anna Thomson (2)