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Starring:

Sean Penn

Acting credits By Highest US Gross

By Year
By UK Gross
By US Gross
By Global Gross
Starring With
Total Gross
1.

The Angry Birds Movie / 2016

Director(s):
Clay Kaytis • Fergal Reilly

Starring:
Jason Sudeikis • Josh Gad • Danny McBride • Maya Rudolph • Bill Hader
$107,509,366
2.

Mystic River / 2003

Director(s):
Clint Eastwood

Starring:
Sean Penn • Tim Robbins • Kevin Bacon • Laurence Fishburne • Marcia Gay Harden
$90,135,191
3.

The Interpreter / 2005

Director(s):
Sydney Pollack

Starring:
Nicole Kidman • Sean Penn • Catherine Keener • Jesper Christensen • Yvan Attal
$72,708,161
4.

Risky Business / 1983

Director(s):
Paul Brickman

Starring:
Tom Cruise • Rebecca De Mornay • Joe Pantoliano • Richard Masur • Bronson Pinchot
$63,541,777
5.

The Secret Life of Walter Mitty / 2013

Director(s):
Ben Stiller

Starring:
Ben Stiller • Kristen Wiig • Jon Daly • Kathryn Hahn • Terence Bernie Hines
$58,236,838
6.

The Game / 1997

Director(s):
David Fincher

Starring:
Michael Douglas • Sean Penn • Deborah Kara Unger • James Rebhorn • Peter Donat
$48,323,648
7.

Colors / 1988

Director(s):
Dennis Hopper

Starring:
Sean Penn • Robert Duvall • Maria Conchita Alonso • Randy Brooks • Grand L. Bush
$46,616,067
8.

Gangster Squad / 2013

Director(s):
Ruben Fleischer

Starring:
Sean Penn • Holt McCallany • Wade Williams • James Landry Hebert • Ambyr Childers
$46,000,903
9.

I Am Sam / 2001

Director(s):
Jessie Nelson

Starring:
Sean Penn • Michelle Pfeiffer • Dakota Fanning • Dianne Wiest • Loretta Devine
$40,311,852
10.

Dead Man Walking / 1996

Director(s):
Tim Robbins

Starring:
Susan Sarandon • Sean Penn • Robert Prosky • Raymond J. Barry • R. Lee Ermey
$39,363,635
11.

Carlito's Way / 1994

Director(s):
Brian De Palma

Starring:
Al Pacino • Sean Penn • Penelope Ann Miller • John Leguizamo • Ingrid Rogers
$36,948,322
12.

The Thin Red Line / 1999

Director(s):
Terrence Malick

Starring:
Sean Penn • Adrien Brody • Jim Caviezel • Ben Chaplin • George Clooney
$36,400,491
13.

Taps / 1981

Director(s):
Harold Becker

Starring:
George C. Scott • Timothy Hutton • Ronny Cox • Sean Penn • Tom Cruise
$35,856,053
14.

Milk / 2009

Director(s):
Gus Van Sant

Starring:
Sean Penn • Josh Brolin • Emile Hirsch • James Franco • Diego Luna
$31,789,774
15.

Fast Times At Ridgemont High / 1982

Director(s):
Amy Heckerling

Starring:
Sean Penn • Jennifer Jason Leigh • Judge Reinhold • Robert Romanus • Brian Backer
$27,092,880
16.

Being John Malkovich / 2000

Director(s):
Spike Jonze

Starring:
John Cusack • Cameron Diaz • Ned Bellamy • Eric Weinstein • Madison Lanc
$22,863,596
17.

Licorice Pizza / 2021

Director(s):
Paul Thomas Anderson

Starring:
Alana Haim • Cooper Hoffman • Sean Penn • Tom Waits • Bradley Cooper
$17,318,007
18.

The Falcon and the Snowman / 1985

Director(s):
John Schlesinger

Starring:
Timothy Hutton • Sean Penn • Pat Hingle • Joyce Van Patten • Rob Reed
$17,130,087
19.

21 Grams / 2004

Director(s):
Alejandro G. Iñárritu

Starring:
Sean Penn • Naomi Watts • Danny Huston • Carly Nahon • Claire Pakis
$16,248,701
20.

The Tree of Life / 2011

Director(s):
Terrence Malick

Starring:
Brad Pitt • Sean Penn • Jessica Chastain • Hunter McCracken • Laramie Eppler
$13,303,319
21.

The Gunman / 2015

Director(s):
Pierre Morel

Starring:
Sean Penn • Jasmine Trinca • Javier Bardem • Ray Winstone • Mark Rylance
$10,664,749
22.

Fair Game / 2011

Director(s):
Doug Liman

Starring:
Naomi Watts • Sean Penn • Anand Tiwari • Michael Kelly • Ty Burrell
$9,528,092
23.

All the King's Men / 2006

Director(s):
Steven Zaillian

Starring:
Sean Penn • Jude Law • Anthony Hopkins • Kate Winslet • Mark Ruffalo
$7,221,458
24.

She's So Lovely / 1997

Director(s):
Nick Cassavetes

Starring:
Sean Penn • Robin Wright • John Travolta • James Gandolfini • Susan Traylor
$5,034,431
25.

Persepolis / 2008

Director(s):
Vincent Paronnaud • Marjane Satrapi

Starring:
Chiara Mastroianni • Catherine Deneuve • Danielle Darrieux • Simon Abkarian • Gabrielle Lopes Benites
$4,435,405
26.

Before Night Falls / 2001

Director(s):
Julian Schnabel

Starring:
Olatz Lpez Garmendia • Giovanni Florido • Lol Navarro • Sebastin Silva • Carmen Beato
$4,242,892
27.

Sweet and Lowdown / 1999

Director(s):
Woody Allen

Starring:
Woody Allen • Ben Duncan • Daniel Okrent • Dan Moran • Tony Darrow
$4,197,015
28.

Up At the VIlla / 2000

Director(s):
Philip Haas

Starring:
Kristin Scott Thomas • Sean Penn • Anne Bancroft • James Fox • Jeremy Davies
$2,834,431
29.

U Turn / 1998

Director(s):
Oliver Stone

Starring:
Sean Penn • Jennifer Lopez • Nick Nolte • Powers Boothe • Claire Danes
$2,730,440
30.

Shanghai Surprise / 1986

Director(s):
Jim Goddard

Starring:
Sean Penn • Madonna • Paul Freeman • Richard Griffiths • Philip Sayer
$2,209,013
31.

We're No Angels / 1989

Director(s):
Neil Jordan

Starring:
Robert De Niro • Sean Penn • Demi Moore • Hoyt Axton • Bruno Kirby
$2,047,630
32.

State of Grace / 1990

Director(s):
Phil Joanou

Starring:
Sean Penn • Ed Harris • Gary Oldman • Robin Wright • John Turturro
$1,911,542
33.

What Just Happened / 2008

Director(s):
Barry Levinson

Starring:
Robert De Niro • Sean Penn • Catherine Keener • Bruce Willis • John Turturro
$1,089,365
34.

The Assassination of Richard Nixon / 2005

Director(s):
Niels Mueller

Starring:
Sean Penn • Naomi Watts • Don Cheadle • Jack Thompson • Brad Henke
$697,759
35.

Flag Day / 2021

Director(s):
Sean Penn

Starring:
Dylan Penn • Sean Penn • Josh Brolin • Regina King • Mitchell McCormick
$423,368
36.

I'm Still Here / 2010

Director(s):
Casey Affleck

Starring:
Joaquin Phoenix • Antony Langdon • Carey Perloff • Larry McHale • Casey Affleck
$408,983
37.

At Close Range / 1986

Director(s):
James Foley

Starring:
Sean Penn • Christopher Walken • Mary Stuart Masterson • Chris Penn • Millie Perkins
$180,286
38.

Black Flies / 2024

Director(s):
Jean-Stephane Sauvaire

Starring:
Sean Penn • Tye Sheridan • Gbenga Akinnagbe • Michael Pitt • Katherine Waterston
$132,898
39.

The Weight of Water / 2000

Director(s):
Kathryn Bigelow

Starring:
Elizabeth Hurley • Catherine McCormack • Sean Penn • Sarah Polley • Ciarán Hinds
$102,622
40.

This Must Be the Place / 2012

Director(s):
Paolo Sorrentino

Starring:
Sean Penn • Frances McDormand • Judd Hirsch • Eve Hewson • Kerry Condon
$87,224
41.

Crackers / 1984

Director(s):
Louis Malle

Starring:
Donald Sutherland • Jack Warden • Sean Penn • Wallace Shawn • Larry Riley
$58,689
42.

Hugo Pool / 1997

Director(s):
Robert Downey Sr.

Starring:
Alyssa Milano • Patrick Dempsey • Robert Downey Jr. • Richard Lewis • Malcolm McDowell
$13,330
43.

Pauly Shore Is Dead / 2003

Director(s):
Pauly Shore

Starring:
Ashley L. Anderson • Pamela Anderson • Camille Anderson • Beaumont Bacon • Adam Barnhardt
$11,000
44.

It's All About Love / 2003

Director(s):
Thomas Vinterberg

Starring:
Joaquin Phoenix • Claire Danes • Sean Penn • Douglas Henshall • Alun Armstrong
$2,582