Sean Penn’s all-time favourite actor: “The biggest blessing I’ve ever come across”
It might seem unusual for an actor to name one of their peers as the greatest thespian they’ve ever worked with when they’ve never even shared a single scene together, but Sean Penn doesn’t seem to mind that he’s never gone toe-to-toe with his idol onscreen.
It’s also unusual for an actor-turned-director to never appear onscreen in any of their features, but Penn has made a point of ensuring his focus is always placed behind the camera. The rule always has exceptions, of course, with the two-time Academy Award winner breaking his in the name of family.
2021’s drama Flag Day was the sixth movie Penn had directed, but the first in which he played a role. As a family-driven story where his daughter Dylan played the lead and son Hopper had a key supporting part, he was happy to disavow his previous insistence on operating only as a filmmaker when he could share the spotlight with his real-life kids.
Speaking of which, Hopper Jack Penn got his name from one of his old man’s friends, inspirations and influences, while the kid’s middle name was taken from somebody who didn’t only travel in the same circles as counterculture icon and legendary hellraiser Dennis Hopper, but ended up as Sean’s favourite actor and most celebrated creative collaborator.
As mentioned, they’ve never been part of the same cast, but Penn and Jack Nicholson proved themselves to be excellent foils nonetheless. The former directed the latter on 1995’s The Crossing Guard and 2001’s The Pledge, and the pair struck up a bond that extended far beyond the final day of principal photography.
“I love this guy in every way,” he told Alex Simon. “Just a great fucking guy. Brilliant all the way around. He’s just the biggest blessing I’ve ever come across in this business. Just a gift. Collaborating with him becomes seamless after a point. We start early, a year early, talk it out, layer it out. I’ll go back to the drawing board on the script, hammer it out. He’ll come up with ideas, and we’ll incorporate them. By the time we get going, it’s just effortless.”
As anyone would expect from one of the best actors in cinema history, Nicholson was reliably excellent in his two Penn-helmed flicks, with The Pledge in particular boasting one of the most underrated and overlooked performances of his storied career. That’s the downside about being an all-timer, though; there’s so much greatness to choose from that some of it tends to fall by the wayside.
Their paths wouldn’t cross again in a professional capacity before Nicholson withdrew from the business in 2012, but it’ll take somebody pretty special to dislodge him from the top spot as both Penn’s favourite actor and favourite person to direct.
