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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.
R Movie (Year) UMR Co-Star Links Adj. B.O. Worldwide (mil) Review Oscar Nom / Win UMR Score
R Movie (Year) UMR Co-Star Links Actual B.O. Domestic (mil) Adj. B.O. Domestic (mil) Adj. B.O. Worldwide (mil) B.O. Rank by Year Review Oscar Nom / Win UMR Score S
1 Mystic River (2003)
AA Best Picture Nom
AA Best Actor Win
Kevin Bacon &
Directed by Clint Eastwood
90.10 186.8 325.10 33 87 06 / 02 99.1
4 Dead Man Walking (1995)
AA Best Actor Nom
Susan Sarandon 43.70 125.6 125.60 39 86 04 / 01 93.6
3 The Thin Red Line (1998)
AA Best Picture Nom
John Travolta &
John Cusack
36.40 97.0 261.50 57 81 07 / 00 91.0
2 Milk (2008)
AA Best Picture Nom
AA Best Actor Win
James Franco 31.80 55.4 95.00 89 89 08 / 02 90.5
6 Colors (1988) Robert Duvall 46.60 141.8 141.80 21 74 00 / 00 89.7
6 One Battle After Another (2025)
AA Best Picture Nom
AA Best Supp Actor Nom
Leonardo DiCaprio 71.50 71.5 205.10 30 80 13 / 00 88.8 NP
8 Taps (1981) George C. Scott &
Tom Cruise
35.90 161.2 161.20 16 67 00 / 00 88.8
7 Carlito's Way (1993) Al Pacino 36.90 111.6 192.80 41 80 00 / 00 88.3
9 The Game (1997) Michael Douglas 48.30 131.6 298.00 40 72 00 / 00 87.9
10 Fast Times at Ridgemont High (1982) Directed by Cameron Crowe 27.10 115.2 115.20 28 74 00 / 00 86.7
11 The Interpreter (2005) Nicole Kidman 72.70 142.0 318.30 33 64 00 / 00 86.1
10 Licorice Pizza (2021)
AA Best Picture Nom
Bradley Cooper &
Directed by Paul Thomas Anderson
16.10 18.6 31.20 50 91 03 / 00 85.4
13 The Angry Birds Movie (2016)
Voice Only
Jason Sudeikis 107.50 155.4 505.50 27 55 00 / 00 84.3
13 The Tree of Life (2011)
AA Best Picture Nom
Brad Pitt &
Jessica Chastain
13.30 21.0 85.60 133 88 03 / 00 83.4
14 Into the Wild (2007) Emile Hirsch &
Vince Vaughn
18.40 33.3 102.20 111 82 02 / 00 78.6
16 The Falcon and the Snowman (1985) Timothy Hutton 17.10 60.3 60.30 52 73 00 / 00 77.7
16 Casualties of War (1989) Michael J. Fox 18.70 58.8 58.80 55 74 00 / 00 77.6
17 21 Grams (2003) Benicio Del Toro &
Naomi Watts
16.30 33.8 125.30 114 79 02 / 00 76.7
20 The Secret Life of Walter Mitty (2013) Ben Stiller 58.20 89.5 289.30 60 62 00 / 00 75.5
18 The Pledge (2001) Jack Nicholson 19.70 43.7 65.10 101 76 00 / 00 75.3
22 I Am Sam (2001)
AA Best Actor Nom
Michelle Pfeiffer &
Dakota Fanning
40.30 89.2 216.40 61 59 01 / 00 74.4
21 Bad Boys (1983) Ally Sheedy 9.20 36.5 36.50 68 73 00 / 00 71.4
22 Before Night Falls (2000) Johnny Depp &
Javier Bardem
4.20 9.8 19.80 147 81 01 / 00 71.3
23 At Close Range (1986) Christopher Walken &
Chris Penn
2.30 7.9 7.90 142 79 00 / 00 67.7
24 Sweet and Lowdown (1999)
AA Best Actor Nom
Directed by Woody Allen 4.20 10.4 10.40 156 77 02 / 00 67.6
25 State of Grace (1990) Gary Oldman &
Ed Harris
1.90 5.6 5.60 152 78 00 / 00 65.7
25 Fair Game (2010) Naomi Watts &
Ty Burrell
9.50 15.1 38.30 130 75 00 / 00 65.2
26 The Indian Runner (1991) David Morse 0.20 0.6 0.60 207 72 00 / 00 53.9
32 Gangster Squad (2013) Ryan Gosling &
Emma Stone
46.00 70.7 161.70 71 48 00 / 00 51.0
27 The Assassination of Richard Nixon (2004) Naomi Watts 0.70 1.4 8.90 214 70 00 / 00 51.0
29 Racing with the Moon (1984) Nicolas Cage 6.00 22.5 22.50 102 63 00 / 00 51.0
30 U Turn (1997) Jennifer Lopez &
Directed by Oliver Stone
6.70 18.2 18.20 130 63 00 / 00 47.8
31 This Must Be the Place (2011) Frances McDormand 0.10 0.2 18.60 231 67 00 / 00 44.7
34 We're No Angels (1989) Robert DeNiro 10.60 33.2 33.20 80 57 00 / 00 44.6
33 She's So Lovely (1997) John Travolta 7.30 19.8 19.80 126 60 00 / 00 43.2
35 The Professor and the Madman (2019) Mel Gibson 0.10 0.1 7.30 375 64 00 / 00 38.5
36 The Crossing Guard (1995) Jack Nicholson 0.90 2.5 2.50 197 63 00 / 00 36.8
37 Daddio (2024) Dakota Johnson 1.00 1.0 1.00 158 63 00 / 00 36.4
37 Up at the Villa (2000) Kristin Scott Thomas &
Anne Bancroft
2.90 6.8 8.70 159 59 00 / 00 31.8
38 Hurlyburly (1998) Meg Ryan 1.80 4.8 4.80 176 59 00 / 00 29.8
39 Flag Day (2021) Josh Brolin 0.30 0.4 0.40 118 57 00 / 00 25.0
40 What Just Happened (2008) Bruce Willis &
Robert DeNiro
1.10 1.9 11.70 201 55 00 / 00 21.9
41 Asphalt City (2024)
Limited Release
0.20 0.2 0.30 183 55 00 / 00 20.5
44 Judgment in Berlin (1988) Martin Sheen 0.20 0.7 0.70 234 54 00 / 00 19.2
45 Loved (1997) William Hurt 0.00 0.1 0.10 334 49 00 / 00 11.8
46 The Weight of Water (2002) Josh Lucas 0.10 0.3 0.30 255 48 00 / 00 10.7
47 The Last Face (2016) Charlize Theron &
Javier Bardem
0.10 0.1 1.80 305 47 00 / 00 9.1
47 The Gunman (2015) Javier Bardem 10.70 15.8 35.80 117 39 00 / 00 7.1
49 All the King's Men (2006) Mark Ruffalo &
Anthony Hopkins
7.20 13.7 18.00 171 37 00 / 00 5.3
50 Crackers (1984) Donald Sutherland 0.10 0.5 0.50 190 40 00 / 00 4.1
50 It's All About Love (2003) Joaquin Phoenix 0.10 0.1 1.00 270 35 00 / 00 1.8
52 Hugo Pool (1997) Robert Downey Jr. 0.10 0.1 0.10 265 32 00 / 00 1.1
52 Shanghai Surprise (1986) Madonna 2.30 7.8 7.80 143 26 00 / 00 0.5

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”

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Older comments
  1. BOB says:
    March 22, 2017 at 7:49 am

    HI BRUCE

    1 You should be more selective about which comment you read. For example I think you could skip those of Steve and John and you would miss nothing and in fact could end up less confused.

    Reply
    1. Cogerson says:
      March 22, 2017 at 8:01 am

      Hey Bob. Your comment made me laugh. I imagine they are thinking the same thing about your comments……lol.

      Reply
  2. BOB says:
    March 18, 2017 at 5:30 am

    1 As articulated above Sean Penn is now in that small group of actors with more than one Academy Award. However any time people whom I know are asked to name the actors with more than single Oscar success they get most of them such as Tracy, Nicholson and Hanks but normally there is surprise when they finally have to be told that Penn is also in the group.

    2 So it would seem that Sean may have achieved acting greatness largely under the radar of the general public . The clue is possibly in the revelation that Sean has the penultimate lowest average Cogerson box office gross of all time and of the two movies for which Sean won Oscars only Mystic River did well commercially and of course it had the Eastwood connection.

    Full many a gem of purest ray serene
    The dark unfathomed caves of ocean bear,
    Full many a flower is born to blush unseen
    And waste its sweetness of the desert air

    3 Thankfully though none of Sean Penn’s achievements have escaped the notice of this site and I for one appreciate this comprehensive profile of his career and the page demonstrates once again that the site is broad based in recognising worthy performers even if the are not huge box office draws. .

    Reply
    1. Cogerson says:
      March 22, 2017 at 7:02 am

      Hey Bob
      1. Sorry I am so far behind in comments. And each day I get further and further behind.
      2. Thanks for your comments on Sean Penn.
      3. Well at least Penn did top Judd Nelson’s average box office total….lol.
      4. You are 100% correct……he seems to be the name people forget when naming the multiple Best Actor Oscar winners.
      5. Milk is almost a forgotten film. Mystic River will probably be the movie that he gets remembered for….and as you say…Mr. Eastwood has a lot to do with that.
      6. As always…thanks for the feedback.

      Reply

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