Ranking the Best Performances to Date from Sean Penn

Sean Penn is widely regarded as one of the best actors of his generation. Even if you can’t quite go that far, he’s undeniably one of the most intense. Two Academy Awards certainly speak to his talents, though a host of other performances do the same. As he gets some of his best reviews in years for a chilling supporting turn in One Battle After Another, looking at Penn’s top tier filmography seemed to be well in order. So, I’ve done just that…

In my review of One Battle After Another (here) earlier in the week, I said the following about the cast, including Penn:

Leonardo DiCaprio is an underrated comic actor, as seen in The Wolf of Wall Street. Here, he gets to play perpetually stoned and continually finds ways to make it hilarious. Whether it’s physical comedy or his tendency to forget the group’s code words, you’re laughing at Bob throughout. DiCaprio is a reliably great presence in the center of the film, though the women in his life really shine brightest. Teyana Taylor is a force of nature, owning the first act of the movie, while Chase Infiniti is the really the star of the final act, announcing herself in a very exciting manner. Taylor gets to literally fuel a revolution, while Infiniti gives one of the more noteworthy breakthrough turns of the year. Then, there’s Sean Penn, who hasn’t been this good in some time, playing Lockjaw as funny, pitiful, and scary in equal measure. You hate the vile man, to be sure, but you’re constantly compelled by him, given the way Penn plays him. Regina Hall has a solid and somber part as one of the former revolutionaries, while Benicio del Toro is having a lot of fun as Willa’s martial arts instructor. His scenes assisting Bob are very enjoyable, while also building to some actual action set-pieces. 

Below, you can see my Penn lineup. Both of his Oscar wins are featured, with Milk representing his best turn to date, at least to me. Mystic River is no slouch, of course, but I think he still did some of his very best work early on with Fast Times at Ridgemont High. One Battle After Another also debuts in a high position here, but how high? Well, read on to find out!

Here now is my ranking of the best performances so far from Sean Penn. Behold:

Honorable Mention: Casualties of War, Flag Day, The Game, Licorice Pizza, and The Secret Life of Walter Mitty

10. The Assassination of Richard Nixon

9. 21 Grams

8. Fair Game

7. Daddio

6. Sweet and Lowdown

5. Mystic River

4. One Battle After Another

3. Dead Man Walking

2. Fast Times at Ridgemont High

1. Milk

What are your favorite performances from Sean Penn? Let us know!