IMDb Page
Movie Release Date Character Age at Release
BC Project 08/08/25 64
Daddio 05/23/24 Clark 63
Asphalt City 03/28/24 Gene Rutkovsky 63
Gonzo Girl 09/07/23 63
Superpower 02/17/23 Self 62
Licorice Pizza 11/26/21 Jack Holden 61
Flag Day 08/20/21 John Vogel 61
Val 07/23/21 Self (archive footage) 60
Friends: The Reunion 05/27/21 (archive footage) 60
Charles Bronson, le génie du mâle 11/29/20 Self (archive footage) 60
Citizen Penn 09/24/20 Himself 60
Fast Times at Ridgemont High: A Virtual Table Read 09/17/20 Pizza Guy 60
The Professor and the Madman 03/07/19 Dr. William Chester Minor 58
Sound of Sun 01/14/17 Man 56
Mad Hannans 01/01/17 56
The Angry Birds Movie 05/11/16 Terence (voice) 55
The Gunman 02/16/15 Jim Terrier 54
Sweet Micky for President 01/23/15 Self 54
Beaver Trilogy Part IV 01/23/15 Himself (archive footage) 54
Return to the Wild: The Chris McCandless Story 11/25/14 Himself 54
Holbrook/Twain: An American Odyssey 06/15/14 Himself 53
The Night That Changed America: A Grammy Salute to the Beatles 02/09/14 Self 53
The Secret Life of Walter Mitty 12/18/13 Sean O'Connell 53
The Human Experiment 11/23/13 Narrator 53
Gangster Squad 01/09/13 Mickey Cohen 52
Americans 10/10/12 Commie 52
Haiti Untold 01/01/12 51
Woody Allen: A Documentary 11/20/11 Self 51
This Must Be the Place 08/24/11 Cheyenne 51
The Tree of Life 05/17/11 Jack 50
I'm Still Here 09/10/10 Sean Penn (uncredited) 50
Fair Game 05/20/10 Joseph Wilson 49
The People Speak 12/13/09 Self 49
Deflating the Elephant 05/19/09 Narrator 48
Milk 11/05/08 Harvey Milk 48
What Just Happened 10/17/08 Himself 48
Witch Hunt 09/07/08 Himself (Narrator) 48
VH1 Rock Honors: The Who 07/17/08 Self 47
Brando 05/01/07 Self 46
Buy the Ticket, Take the Ride 12/12/06 Self 46
All the King's Men 09/10/06 Willie Stark 46
The Interpreter 04/08/05 Tobin Keller 44
The Cutting Edge: The Magic of Movie Editing 10/12/04 Self 44
The Assassination of Richard Nixon 05/17/04 Samuel Bicke 43
Dennis Hopper: The Decisive Moments 05/01/04 Self 43
21 Grams: In Fragments 03/16/04 Self 43
21 Grams 09/06/03 Paul Rivers 43
Pauly Shore Is Dead 03/11/03 Sean Penn 42
Mystic River 03/03/03 Jimmy Markum 42
Dennis Hopper: Create (or Die) 02/10/03 Self 42
Bukowski: Born Into This 01/18/03 Himself 42
It's All About Love 01/10/03 Marciello 42
This So-Called Disaster: Sam Shepard Directs "The Late Henry Moss" 01/01/03 Ray 42
Inside Björk 01/01/03 Self 42
Rosy-Fingered Dawn: A Film on Terrence Malick 09/01/02 Self 42
Searching for Debra Winger 07/13/02 Self (uncredited) 41
I Am Sam 12/28/01 Sam Dawson 41
Dogtown and Z-Boys 01/18/01 Narrator 40
The Beaver Trilogy 12/31/00 "Groovin' Larry" Huff 40
The Weight of Water 09/25/00 Thomas Janes 40
Before Night Falls 09/03/00 Cuco Sanchez 40
Up at the Villa 04/14/00 Rowley Flint 39
A Constant Forge 01/01/00 Self 39
Reliving Our Fast Times at Ridgemont High 12/21/99 39
Sweet and Lowdown 12/03/99 Emmet Ray 39
Being John Malkovich 10/29/99 Sean Penn (uncredited) 39
Hurlyburly 12/25/98 Eddie 38
The Thin Red Line 12/23/98 1st Sgt. Edward Welsh 38
Hugo Pool 12/12/97 Strange Hitchhiker 37
Loved 10/31/97 Man on the Hill (Michael) 37
U Turn 10/03/97 Bobby Cooper 37
The Game 09/12/97 Conrad Van Orton 37
She's So Lovely 08/29/97 Eddie Quinn 37
Dead Man Walking 12/29/95 Matthew Poncelet 35
Carlito's Way 11/10/93 David Kleinfeld 33
The Last Party 08/27/93 Self 33
Madonna: The Name of the Game 01/01/93 Himself 32
Cruise Control 10/01/92 32
State of Grace 09/14/90 Terry 30
Cool Blue 02/27/90 Phil the Plumber (uncredited) 29
Casualties of War 08/18/89 Sgt. Tony Meserve 29
We're No Angels 06/02/89 Jim 28
Judgment in Berlin 05/06/88 Guenther X 27
Colors 04/15/88 Danny McGavin 27
Dear America: Letters Home from Vietnam 10/01/87 (voice) 27
Shanghai Surprise 08/29/86 Glendon Wasey 26
At Close Range 04/18/86 Bradford "Brad" Whitewood Jr. 25
The Falcon and the Snowman 01/25/85 Daulton Lee 24
Racing with the Moon 03/23/84 Henry 'Hopper' Nash 23
Crackers 02/17/84 Dillard 23
Summerspell 07/02/83 Buddy 22
Bad Boys 03/25/83 Mick O’Brien 22
Fast Times at Ridgemont High 08/13/82 Jeff Spicoli 21
Taps 12/20/81 Cadet Captain Alex Dwyer 21
The Beaver Kid 2 09/04/81 Groovin' Larry 21
The Killing of Randy Webster 03/11/81 Don Fremont 20
Hellinger's Law 03/10/81 Bit Part (uncredited) 20
Війна очима тварин None 63