The one actor Paul Thomas Anderson called the most iconic of all time: “There’s nothing funny about it”
One of the benefits of being not just one of the most respected auteurs in the industry but arguably the best actors’ director in the business is that legends, icons, and A-listers aren’t just falling over themselves to try and work with Paul Thomas Anderson: they know there’s a high chance he’ll steer them towards one of the best performances of their careers.
Denzel Washington doesn’t go out of his way to track down high-calibre filmmakers because he’s in a similar position to Anderson on the other side of the camera: he’s the guy everybody wants to direct. And yet, the two-time Academy Award winner has made it his mission to partner with PTA before he calls it a day.
Burt Reynolds? An icon of his era who gave a career-best turn in Boogie Nights and earned his one and only Oscar nomination in the process. Sure, he hated Anderson’s guts, but he was still great in the movie. Daniel Day-Lewis? One of the all-time greats, who won another Oscar for leading There Will Be Blood.
Adam Sandler? He gave his best performance on Anderson’s watch and made the Golden Globes shortlist. Tom Cruise? He also gave his best performance on Anderson’s watch and netted his third – and so far final – Oscar nomination for acting. Joaquin Phoenix, Philip Seymour Hoffman, Amy Adams, Julianne Moore, and on it goes, talented stars in their own right, but on a level above in a PTA flick.
One name escaped him from the very beginning, though, and Anderson was determined to eventually cast them no matter the when, what, where, why, and how. He got his wish, but he made a very bold proclamation when he suggested that there wasn’t a name in the history of cinema that could be declared as more iconic.
“I wanted to find somebody who felt iconic, and there’s no one more iconic than Sean Penn,” Anderson said to Variety, tasking the two-time Oscar winner to play Jack Holden in Licorice Pizza. “I’ve been asking Sean Penn to be in movies for as long as I’ve been doing this. I wanted him for Boogie Nights in the part that Alfred Molina ended up playing in the firecracker scene. I talked to him around the time of Punch-Drunk Love.”
Anderson didn’t want to hire somebody for the sole purpose of having them do an impression of William Holden, on whom the character was based. Instead, he wanted someone who would play it completely straight, and they don’t get much more serious than Penn, whether it’s for better or worse.
“What’s nice about his performance is there’s nothing funny about it,” Anderson explained of Penn’s stoic approach to the part. “Sean does not play one thing for the gag. He plays the utmost seriousness and delusions of an actor. That’s hilarious.”
Then again, maybe Penn didn’t have to try all that hard when he’s known for taking himself very seriously. Either way, after he finally wrangled him into an ensemble, he’ll do it again when they reunite for 2025’s The Battle of Baktan Cross.
