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… 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.
  • Use the search and sort buttons to make this page very interactive. For example…type in “DeNiro” in the search box and up pop the 2 Robert DeNiro/Penn movies
RankMovie (Year)UMR Co-Star LinkAdj. B.O. Domestic (mil)Box Office Rank by YearCritic Audience RatingOscar Nom / WinUMR Score
Mystic River (2003)Kevin Bacon & Directed by Clint Eastwood$126.0033rd of 200383.50%06 / 0274.82
Milk (2008)James Franco$37.4089th of 200886.00%08 / 0261.62
Dead Man Walking (1995)Susan Sarandon$76.3042nd of 199584.50%04 / 0159.27
Thin Red Line, The (1998)John Travolta & John Cusack$65.4059th of 199877.00%07 / 0051.30
Carlito's Way (1993)Al Pacino$75.2042nd of 199380.50%00 / 0050.87
Taps (1981)George C. Scott & Tom Cruise$108.7018th of 198172.50%00 / 0050.62
Colors (1988)Robert Duvall$95.6021st of 198873.50%00 / 0049.88
Game, The (1997)Michael Douglas$88.8041st of 199773.50%00 / 0048.86
I Am Sam (2001)Michelle Pfeiffer & Dakota Fanning$60.1061st of 200170.00%01 / 0047.12
Fast Times at Ridgemont High (1982)Directed by Cameron Crowe$77.7029th of 198274.00%00 / 0046.82
Tree of Life, The (2011)Brad Pitt & Jessica Chastain$14.10132nd of 201183.50%03 / 0044.88
Sweet and Lowdown (1999)Directed by Woody Allen$7.00161st of 199975.50%02 / 0043.11
Interpreter, The (2005)Nicole Kidman$95.8033rd of 200560.00%00 / 0043.05
Casualties of War (1989)Michael J. Fox$39.6058th of 198978.00%00 / 0042.85
Into the Wild (2007)Emile Hirsch & Vince Vaughn$22.50114th of 200782.00%02 / 0042.79
Angry Birds Movie, The (2016)Jason Sudeikis$107.5026th of 201654.00%00 / 0042.50
Falcon and the Snowman, The (1985)Timothy Hutton$40.7052nd of 198576.00%00 / 0042.03
Bad Boys (1983)Ally Sheedy$24.6075th of 198380.50%00 / 0041.65
21 Grams (2003)Benicio Del Toro & Naomi Watts$22.80119th of 200378.50%02 / 0041.22
Pledge, The (2001)Jack Nicholson$29.40102nd of 200173.50%00 / 0039.04
At Close Range (1986)Christopher Walken & Chris Penn$5.30141st of 198681.00%00 / 0038.94
Secret Life of Walter Mitty, The (2013)Ben Stiller$60.4042nd of 201362.50%00 / 0038.58
State of Grace (1990)Gary Oldman & Ed Harris$3.80156th of 199078.50%00 / 0037.48
Fair Game (2010)Naomi Watts & Ty Burrell$10.20134th of 201073.50%00 / 0036.12
Before Night Falls (2000)Johnny Depp & Javier Bardem$6.60165th of 200073.50%01 / 0035.96
Indian Runner, The (1991)David Morse$0.40218th of 199172.00%00 / 0033.90
Assassination of Richard Nixon, The (2004)Naomi Watts$1.00238th of 200469.00%00 / 0032.59
Crossing Guard, The (1995)Jack Nicholson$1.70203rd of 199568.50%00 / 0032.48
Racing with the Moon (1984)Nicolas Cage$15.20103rd of 198463.50%00 / 0032.26
U-Turn (1997)Jennifer Lopez & Directed by Oliver Stone$12.30133rd of 199764.50%00 / 0032.23
This Must Be the Place (2009)Frances McDormand$0.20298th of 200966.00%00 / 0031.05
Gangster Squad (2013)Ryan Gosling & Emma Stone$47.7071st of 201350.00%00 / 0030.99
She's So Lovely (1997)John Travolta$13.40128th of 199760.50%00 / 0030.53
We're No Angels (1989)Robert DeNiro$22.4083rd of 198954.00%00 / 0028.86
Hurlyburly (1998)Meg Ryan$3.20190th of 199859.00%00 / 0028.23
What Just Happened (2008)Bruce Willis & Robert DeNiro$1.30218th of 200855.50%00 / 0026.32
Judgment in Berlin (1988)Martin Sheen$0.50217th of 198854.50%00 / 0025.70
Up at the Villa (2000)Kristin Scott Thomas & Anne Bancroft$4.60170th of 200053.00%00 / 0025.62
Weight of Water, The (2002)Josh Lucas$0.20347th of 200248.00%00 / 0022.59
Gunman, The (2015)Javier Bardem$10.70125th of 201537.00%00 / 0019.24
Crackers (1984)Donald Sutherland$0.30165th of 198440.00%00 / 0018.85
All the King's Men (2006)Mark Ruffalo & Anthony Hopkins$9.30174th of 200635.50%00 / 0018.22
It's All About Love (2004)Joaquin Phoenix$0.01506th of 200434.50%00 / 0016.22
Hugo Pool (1997)Robert Downey Jr.$0.01293rd of 199732.00%00 / 0015.05
Shanghai Surprise (1986)Madonna$5.30142nd of 198621.00%00 / 0010.69

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’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.

If you do a comment….please ignore the email address and website section.

(Visited 553 times)

17 thoughts on “Sean Penn Movies


    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.

  2. 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. .

    1. 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.

Leave a Reply

Your email address will not be published.