IMDb Page
Movie Release Date Character Age at Release
American Badass: A Michael Madsen Retrospective 08/15/22 Self 56
kid 90 03/12/21 Self (archive footage) 55
(My) Truth: The Rape of 2 Coreys 03/09/20 Self (archive footage) 54
Grizzly II: Revenge 02/17/20 Lance 54
#NoJoke 09/09/19 Self 54
Race Against Time 06/01/19 53
Brothers in Arms 11/13/18 Narrator (voice) 53
I Am Sam Kinison 12/19/17 Himself 52
9/11 09/07/17 Jeffrey Cage 52
Mad Families 01/12/17 Charlie 51
Must See TV: An All Star Tribute to James Burrows 02/21/16 Self 50
Brothers in War 03/26/14 Narrator (voice) 48
Machete Kills 09/12/13 Mr. President 48
Scary Movie 5 04/11/13 Charlie Sheen 47
Milius 03/09/13 Self 47
A Glimpse Inside the Mind of Charles Swan III 02/08/13 Charles Swan III 47
Madea's Witness Protection 06/29/12 Self 46
Foodfight! 06/15/12 Dex Dogtective (voice) 46
She Wants Me 04/05/12 Charlie 46
Comedy Central Roast of Charlie Sheen 09/19/11 Himself - Roastee 46
9/11 Truth: Hollywood Speaks Up 06/10/11 Himself 45
Due Date 11/03/10 Charlie Harper 45
Wall Street: Money Never Sleeps 09/20/10 Bud Fox 45
Scary Movie 4 04/12/06 Tom Logan (uncredited) 40
Guilty Hearts 01/01/06 Himself 40
The Big Bounce 01/30/04 Bob Rogers, Jr. 38
Scary Movie 3 10/24/03 Tom 38
Pauly Shore Is Dead 03/11/03 Charlie Sheen 37
Saturday Night Live: The Best of Will Ferrell 09/28/02 Doctor (archive footage) 37
Good Advice 11/15/01 Ryan Edward Turner 36
A Tour of the Inferno: Revisiting 'Platoon' 01/01/01 Self 35
Lisa Picard Is Famous 05/14/00 Charlie Sheen 34
Rated X 01/25/00 Artie Mitchell 34
Being John Malkovich 10/29/99 Charlie 34
Five Aces 05/28/99 Chris Martin 33
No Code of Conduct 03/19/99 Jake Peterson 33
Free Money 12/03/98 Bud Dyerson 33
A Letter from Death Row 11/17/98 Cop #1 33
Masters of the Martial Arts Presented by Wesley Snipes 08/18/98 Self (archive footage) 32
Postmortem 06/20/98 James McGregor 32
Tudjman 12/31/97 Narrator (voice) 32
Money Talks 08/22/97 James Russell 31
Bad Day on the Block 08/22/97 Lyle Wilder 31
Loose Women 07/18/97 Barbie Loving Bartender 31
Shadow Conspiracy 01/25/97 Bobby Bishop 31
The Arrival 05/31/96 Zane Zaminski 30
All Dogs Go to Heaven 2 03/29/96 Charlie B. Barkin (voice) 30
A Century of Science Fiction 01/01/96 Self 30
Terminal Velocity 09/23/94 Ditch Brodie 29
Charlie Sheen's Stunts Spectacular 06/30/94 Host 28
Major League II 03/30/94 Rick Vaughn 28
The Chase 03/04/94 Jackson Hammond 28
The Three Musketeers 11/11/93 Aramis 28
Deadfall 10/08/93 Morgan "Fats" Gripp 28
Hot Shots! Part Deux 05/21/93 Topper Harley 27
Hearts of Hot Shots! Part Deux—A Filmmaker's Apology 05/20/93 27
Beyond the Law 04/22/93 Daniel 'Dan' Saxon 27
National Lampoon's Loaded Weapon 1 02/04/93 Valet 27
Hot Shots! 07/31/91 Topper Harley / Rhett Butler / Superman 25
The Rookie 12/07/90 David Ackerman 25
Cadence 11/16/90 Pfc. Franklin Fairchild Bean 25
Men at Work 08/24/90 Carl Taylor 24
Navy Seals 07/20/90 Lt. Dale Hawkins 24
Catchfire 04/03/90 Bob 24
Courage Mountain 02/14/90 Peter 24
Never on Tuesday 04/13/89 Thief (uncredited) 23
Major League 02/16/89 Rick Vaughn 23
Tale of Two Sisters 01/01/89 Narrator 23
Eight Men Out 09/02/88 Hap Felsch 22
Young Guns 02/17/88 Dick Brewer 22
Wall Street 12/10/87 Bud Fox 22
No Man's Land 10/23/87 Ted Varrick 22
Three for the Road 04/10/87 Paul 21
Wisdom 12/31/86 City Burger Manager 21
Platoon 12/19/86 Chris Taylor 21
The Wraith 11/21/86 Jake Kesey / The Wraith 21
Ferris Bueller's Day Off 06/11/86 Boy in Police Station 20
Lucas 03/28/86 Cappie 20
The Boys Next Door 03/14/86 Bo Richards 20
Out of the Darkness 10/12/85 Man Shaving (uncredited) 20
The Fourth Wise Man 03/30/85 Maximus 19
Silence of the Heart 10/30/84 Ken 19
Red Dawn 08/10/84 Matt 18
The Execution of Private Slovik 03/13/74 Kid at Wedding (uncredited) 8
Badlands 01/05/74 Boy Under Lamppost (uncredited) 8