Three-Times Oscar Winner Sean Penn's Best Movies, Ranked
Whatever incarnation of Sean Penn comes to mind when you think of his name — the recent, grizzled version who travelled to Mexico to interview El Chapo and played Steven J. Lockjaw in One Battle After Another; the mid-career icon who won Oscars for Milk and Mystic River; or the long haired stoner Jeff Spicoli who ordered pizza to the classroom in Fast Times at Ridgemont High — I think it’s fair to say that the actor has enjoyed one of the most colourful careers in the last 40 years of American movies.
Preternaturally gifted, consistently intense, and — as his movies as director (Flag Day, The Last Face) have shown — occasionally earnest to a fault, Penn’s work both in front of and behind the camera has always seemed to mirror his personality off it. At its best, this all-encompassing dedication has led to some of the finest performances of the last half-century, ten of which I’ve listed below in ascending order — based both on the movies themselves and Penn’s significance to them.
Read on to learn a little more and use the guide below to find out where to stream them on services like Apple TV, Netflix, Prime Video and elsewhere.
Having earned an Oscar nomination for Best Foreign Language Film for his influential debut, Amores Perros, Mexican director Alejandro González Iñárritu immediately made the jump to Hollywood with 21 Grams and immediately cast Sean Penn in the lead role.
This grittiest of films follows three interweaving stories, one of which concerns a man who kills a father and his two children in a hit and run, only to be given the man’s heart in a subsequent operation. It’s one of the toughest watches from Penn’s back catalogue — a prime example of Iñárritu’s approach before he remembered to put a little humour and pep into his movies (think more Babel than Birdman), but there’s no doubting Penn’s excellence in it.
To be honest, I love Liquorice Pizza so much that it was kind of tough to leave it languishing in ninth place here. The reason for its placement is that, while Penn certainly kicked off a comeback with his role as the leathery Hollywood star Jack Holden here, he doesn’t have the kind of screen time to warrant it overtaking the other movies on this list.
Pizza is, I think, Paul Thomas Anderson’s most nostalgic and joyful film to date — a coming-of-age tale that lets you feel what it might have actually been like to be young and in love in the San Fernando Valley in the 1970s.
It’s probably true that Penn has roughly the same amount of screen time in Fast Times at Ridgemont High as he does in PTA’s Pizza, but of his early roles, it was just too iconic to leave out. Amongst his earlier roles, we could have mentioned the juvie-set drama Bad Boys or James Foley’s At Close Range, but Fast Times basically lodged that image of Penn as the affable, long-haired stoner into the minds of every single person who saw it.
Fast Times was also Cameron Crowe’s breakout hit, so if you’re an appreciator of all things Almost Famous, it’s well worth going back to check this one out.
Okay, so fair warning: Sweet and Lowdown is a Woody Allen movie. It’s also one of the most interesting lead roles that Penn — an actor who also excels in supporting parts — has ever taken on.
Essentially a retelling of Fellini’s classic La Strada, Sweet and Lowdown sees Penn play a Django Reinhardt-obsessed jazz guitarist who falls in love with a mute woman — played by Samantha Morton — in 1930s Chicago. It’s the kind of thing that makes you wish he did more straight-up comedy.
You certainly won’t find a lot of laughs in either of Penn’s collaborations with Terrence Malick. If I had to choose the one I prefer, I’d certainly go for the director’s peerless 2010 Palme d’Or winner, The Tree of Life — but seeing as Penn spends most of his time in that movie wandering through a metaphysical desert, I felt inclined, for the sake of this list, to go for The Thin Red Line.
This phenomenal Second World War movie was Malick’s long-awaited comeback after a 17-year hiatus following the release of Days of Heaven. As a result, pretty much every male actor in Hollywood wanted to be in it — and by the look of the cast list, most of them got their wish. For that reason, you couldn’t exactly call this one a Penn movie, per se, but it’s a masterpiece and the actor gets top billing, so credit where credit’s due.
I always like films that work as a kind of passing of the baton between generations of great actors — think Redford and Pitt in Spy Game, or Brando, De Niro and Norton in The Score — Hollywood’s best example of a changing of the guard.
With Al Pacino in the lead and Penn supporting, 1993’s Carlito’s Way — a story about a rehabilitated criminal (Pacino) who gets dragged back into his previous life, partially by his lawyer and friend (Penn) — is another prime example of the genre.
If you’re reading this, chances are you’ve already seen Paul Thomas Anderson’s Best Picture-winning One Battle After Another — perhaps even multiple times. So rewatchable is Anderson’s Best Picture winner that, even at close to three hours long, fans just seem to keep going back for more.
The story stars Leonardo DiCaprio as a washed up revolutionary alongside Chase Infiniti as his loving and long-suffering daughter, but it’s Penn’s demented turn as the antagonist, Steven J Lockjaw, that really sticks in the memory long after the credits roll — enough for the Academy to award him with a record-equalling third Oscar, which, of course, he didn’t show up for.
Outside of Mystic River (more on that, shortly), Tim Robbins’ only Oscar recognition in his career, surprisingly enough, was the director nod he received for his 1995 crime drama Dead Man Walking. This was also the first nomination that Penn received, and it remains one of his very best performances — and one of his greatest films.
Penn is said to have gone into intensive research mode to prepare for the job of playing Matthew Poncelat, the death row inmate who forms an unlikely bond with Susan Sarandon's conscientious nun. If you’re a fan of ‘90s movies like Primal Fear and The Shawshank Redemption, make sure to seek this one out.
Eight years after his first nomination, Penn finally won the coveted Best Actor prize for Clint Eastwood’s Mystic River — a deadly serious, Boston-set crime drama that centres on the killing of a 19-year-old girl. Playing the bereaved father, this was a role — along with 21 Grams, released the very same year — that cemented Penn’s reputation as Hollywood’s go-to actor for characters beyond the verge of a nervous breakdown.
Eastwood’s film also won Best Picture that night, but its reputation hasn’t exactly grown over the years. This is likely to do with it being such a tough watch — but if you’re a fan of Penn, it’s naturally worth the effort.
Five years after River, Penn confirmed his reputation as one of the best of his generation when he starred as the queer activist Harvey Milk — the first openly gay person to be elected to major public office in the United States — in Gus Van Sant’s eponymously titled biopic. This was the role that saw him win his second Best Actor award over his old friend Mickey Rourke, who was heavily favoured that year for his comeback turn in The Wrestler.
This was Van Sant’s follow-up to his otherworldly, Columbine-inspired film Elephant — a work that actually beat Mystic River to the Palme d’Or in Cannes in 2003. As topical films go, Milk is far less austere and experimental, but it’s still a must-see. It remains Sean Penn’s finest hour.
