Sean Penn Movies

Want to know the best Sean Penn movies?  How about the worst Sean Penn movies?  Curious about Sean Penn box office grosses or which Sean Penn movie picked up the most Oscar® nominations? Need to know which Sean Penn movie got the best reviews from critics and audiences and which ones got the worst reviews? Well you have come to the right place….because we have all of that information.

Sean Penn (1960-) is a 2-time Oscar®-winning actor and director  Sean Penn has been starring in movies for over 35 years.  His IMDb page shows 62 acting credits and 8 directing credits from 1974-2017. This page will rank 45 Sean Penn movies from Best to Worst in six different sortable columns of information. Television shows, shorts, cameos and movies that were not released in North American theaters were not included in the rankings.

Drivel part of the page:  Why a Sean Penn page?  One…this was a request from many many moons ago.  Two….back in the 1980s….we were huge fans of Sean Penn.  Talk about a great start to a career…first was Taps (which got Tom Cruise going too), then Fast Times At Ridgemont High (his Jeff Spicoli put him on the map and Bad Boys (proved the man could really act).  And finally….of the 9 members of the 2 or more Best Actor Oscar® winner club…Sean Penn was the only that did not have an UMR page.  Well no more…..as we now have a UMR page on him..  *The other members of the 2 or more Best Actor Oscar® club?  Marlon Brando, Gary Cooper, Daniel Day-Lewis (3 time winner), Tom Hanks, Dustin Hoffman, Fredric March, Jack Nicholson and Spencer Tracy.  Pretty good company that Mr. Penn is keeping.

Sean Penn Movies Can Be Ranked 6 Ways In This Table

The really cool thing about this table is that it is “user-sortable”. Rank the movies anyway you want.

  • Sort Sean Penn movies by co-stars of his movies.
  • Sort Sean Penn movies by adjusted domestic box office grosses using current movie ticket cost (in millions)
  • Sort Sean Penn movies by yearly domestic box office rank
  • Sort Sean Penn movies how they were received by critics and audiences.  60% rating or higher should indicate a good movie.
  • Sort by how many Oscar® nominations and how many Oscar® wins each Sean Penn movie received.
  • Sort Sean Penn movies by Ultimate Movie Rankings (UMR) Score.  UMR Score puts box office, reviews and awards into a mathematical equation and gives each movie a score.

Stats and Possibly Interesting Things From The Above Sean Penn Table

  1. Three Sean Penn movies crossed the magical $100 million domestic gross mark.  That is a percentage of 6.67% of his movies listed. Mystic River (2003) is his biggest hit.
  2. An average Sean Penn movie grosses $32.20 million in adjusted box office gross.
  3. Using RottenTomatoes.com’s 60% fresh meter.  31 of Sean Penn movies are rated as good movies…or 68.88% of his movies.  Milk (2008) is his highest rated movie while Shanghai Surprise (1986) is his lowest rated movie.
  4. Ten Sean Penn movie received at least one Oscar® nomination in any category…..or 22.22% of his movies.
  5. Three Sean Penn movies won at least one Oscar® in any category…..or 6.67% of his movies.
  6. An average Ultimate Movie Ranking Score is 39.86.  19 Sean Penn movies scored higher than that average….or 42.22% of his movies.  Mystic River (2003) got the the highest UMR Score while Shanghai Surprise (1986) got the lowest UMR Score.
Sean Penn in 1988’s Colors

Possibly Interesting Facts About Sean Penn

1. Sean Justin Penn was born in Los Angeles, California in 1960.

2. Sean Penn’s father, Leo Penn, was an actor and director.  In 1974 Leo Penn directed his son in his first ever role….an appearance on television’s Little House on the Prairie. Sean Penn’s two brothers are the late actor Chris “Reservoir Dogs” Penn and singer/composer Michael Penn.

3. When still going to school, Sean Penn began making short films with some of his childhood friends, including actors Emilio Estevez and Charlie Sheen.

4. Sean Penn has been nominated for 5 Best Actor Oscars®: 1995’s Dead Man Walking, 1999’s Sweet and Lowdown, 2001’s I Am Sam, 2003’s Mystic River (he won) and 2008’s Milk (he won).

5. Sean Penn has been married two times. His first marriage was to singer and 1986’s Shanghai Suprise co-star, Madonna.  His second marriage was to Robin “Princess Bride” Wright.  Penn and Wright have two children.  Penn’s son, Hopper Jack Penn, is named after Dennis Hopper and Jack Nicholson.

6. Sean Penn’s performance as “Jeff Spicoli” in 1982’s Fast Times at Ridgemont High was ranked #9 on Premiere Magazine’s 100 Greatest Movie Characters of All Time.

7. Sean Penn is very good friends with Robert DeNiro. The two share the same birthday and would often throw a joint birthday party together.

8.  Sean Penn has a cameo in 1983’s Risky Business.  Penn is the man sitting in the passenger seat as Joel first takes the Porsche for a spin. The cameo was a favor for director Paul Brickman. Penn and Cruise had previously starred together in 1981’s Taps.

9.  From the UMR database:  Of all of the UMR subjects we have written about….Sean Penn’s average of $32.20 million in adjusted box office is the 2nd lowest average in our database.  Only Judd Nelson has a lower average per movie.

10. Check out Sean Penn‘s career compared to current and classic actors.  Most 100 Million Dollar Movies of All-Time.

Academy Award® and Oscar® are the registered trademarks of the Academy of Motion Arts and Sciences. Golden Globes® are the registered trademark and service mark of the Hollywood Foreign Press.

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17 thoughts on “Sean Penn Movies

  1. I thought he was severly miscast in The Gunman. Thinking with the way it bombed I am not the only one. Favorites include Mystic River, Fast Times, At Close Range and Bad Boys. Favorite trivia? The second worst box office average, only beating Judd Nelson? Not thinking Penn is bragging about that.

    1. Hey Petetson…I agree The Gunman was not Penn’s finest day. I like all the movies you listed as your favorites. Glad you enjoyed our trivia…and yes that is not something for h to brag about.

  2. I never liked Sean Penn, he’s a good actor I won’t deny but something about him, he doesn’t seem like a nice guy. Sean is #228 on the Oracle of Bacon Center of the Hollywood Universe list (which has been updated again). Actually Sean has dropped to 252 now. These are the people in the most recent top 30 of the countdown whom he appeared with.

    At Close Range (1986) – 28 Christopher Walken
    Colors (1988) – 15 Seymour Cassel
    Crackers (1984) – 9 Donald Sutherland
    Hugo Pool (1997) – 8 Malcolm McDowell
    I’m Still Here (2010) – 18 Bruce Willis
    Judgment in Berlin (1988) – 11 Martin Sheen
    Racing with the Moon (1984) – 2 Michael Madsen
    The Thin Red Line (1998) – 19 John Savage
    We’re No Angels (1989) – 6 Robert De Niro

    Sean has worked with 35 Oscar winners by my count.

    21 Grams (2003) – Benicio Del Toro, Melissa Leo
    All the King’s Men (2006) – Anthony Hopkins, Kate Winslet
    At Close Range (1986) – Christopher Walken
    Carlito’s Way (1993) – Al Pacino
    Colors (1988) – Robert Duvall
    Dead Man Walking (1995) – Susan Sarandon
    Fast Times at Ridgemont High (1982) – Nicolas Cage, Forest Whitaker
    Gangster Squad (2013) – Emma Stone
    Hurlyburly (1998) – Kevin Spacey, Anna Paquin
    I Am Sam (2001) – Mary Steenburgen, Dianne Wiest
    I’m Still Here (2010) – Jack Nicholson, Jamie Foxx, Casey Affleck, Natalie Portman
    Loved (1997) – William Hurt
    Mystic River (2003) – Tim Robbins, Marcia Gay Harden
    Racing with the Moon (1984) – Nicolas Cage
    Taps (1981) – George C. Scott, Timothy Hutton
    The Falcon and the Snowman (1985) – Timothy Hutton
    The Game (1997) – Michael Douglas
    The Gunman (2015) – Javier Bardem, Mark Rylance
    The Interpreter (2005) – Nicole Kidman
    The Secret Life of Walter Mitty (2013) – Shirley MacLaine
    The Thin Red Line (1998) – George Clooney, Adrien Brody, Jared Leto
    This Must Be the Place (2012) – Frances McDormand
    U-Turn (1997) – Jon Voight
    Up at the Villa (2000) – Anne Bancroft
    We’re No Angels (1989) – Robert De Niro

    Mo’Nique, best supporting actress for Precious in 2009 cannot be connected to Sean Penn through anybody!!!! Not 2 steps, not 20 steps. I bet Mo’Nique misses a lot of other people too.

    1. Hey Dan
      1. I understand your thinking on Sean Penn. I really liked him at the start of his career. But his off screen life has turned many people away.
      2. That is a decent Oracle showing…..but then again he has been working steadily for a very long time.
      3. He and Bruce Willis were in What Just Happened as well.
      4. 35 Oscar winners is pretty impressive…especially in the non-studio world we live in.
      5. That is interesting about Mo’Nique….I will probably see if I can figure that one out…..seems her to her co-star in Precious to the Tower Heist should unlock some links.
      Great feedback as always.

      1. I think they have a problem with Mo’Nique. They say Mo’Nique has made 1 film. She does not link to Gabourey Sidibe her co-star in Precious even going through Gabourey which lists her as a co-star but then says she has a number of infinity. I would disregard the Sean Penn comment to her and say the site has problems with Mo’Nique.

        1. You are correct on What Just Happened which also means he has appeared with Robert De Niro twice in a movie, this and We’re No Angels.

        2. Mo to Gabby to Gabby & Ben Stiller in Tower Heist….to Stiller and Penn in Walter Mitty. So I agree they have a mistake there.

  3. I usually don’t comment on current star UMR pages, but I did love Mystic River so I thought I would comment that I have seen 5 Sean Penn movies, all in the top 10.

    1. Hey Flora….thanks for a comment on a current UMR page. Mystic River is an intense excellent movie…..with some great acting from Penn, Robbins and Bacon. Since all 5 of the Penn movies you watched are in the Top 10…tells me our rankings really worked on this page. Thanks again for the feedback.

  4. Hey Cogerson. I liked his earlier movies but have to admit his extreme political views have rubbed me the wrong way. That has made me do an unofficial boycott of his movies. But no matter what I feel today, I remember thinking he was going to be the next DeNiro or Hoffman back in the 1980s. You must be a big fan of his if you have seen 39 of his movies.

    Off the subject. Seems like my last couple of comments have disappeared? Is that something people have complained about recently? Or did I write something that had to be deleted? Just curious.

    1. Hey SteinHOF
      1. Thanks for the visit.
      2. I avoided his political activities completely.
      4. I agree his early career was pretty impressive.
      5. I had heard the comparison to DeNiro but not Hoffman…but the more I think about it….. the more spot on I feel about it.
      6. Mmmmm missing comments…I think Steve had that happen to him as well…..sorry about that….hopefully that issue had bee resolved.
      7. Good feedback.

  5. And I will put out the first tally count….I have seen 39 of these movies. Or 86.66% of his movies. Not thinking anybody will top that tally count.

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