| Alex Dwyer in Taps | 
| Jeff Spicoli in Fast Times at Ridgemont High | 
| Mick O'Brien in Bad Boys | 
| Dillard in Crackers | 
| Daulton Lee in The Falcon and the Snowman | 
| Henry 'Hopper' Nash in Racing with the Moon | 
| Brad Jr. in At Close Range | 
| Glendon Wasey in Shanghai Surprise | 
| Danny McGavin in Colors | 
| Meserve in Casualties of War | 
| Jim in We're No Angels | 
| Terry in State of Grace | 
| Kleinfeld in Carlito's Way | 
| Matthew Poncelet in Dead Man Walking | 
| Conrad in The Game | 
| Eddie in Hurlyburly | 
| Man on the Hill (Michael) in Loved | 
| Eddie Quinn in She's So Lovely | 
| Bobby Cooper in U Turn | 
| 1st Sgt. Welsh in The Thin Red Line | 
| Rowley Flint in Up at the Villa | 
| Emmet Ray in Sweet and Lowdown | 
| Thomas Janes in The Weight of Water | 
| Marciello in It's All About Love | 
| Narrator in Dogtown and Z-Boys | 
| Sam Dawson in I Am Sam | 
| Ray in This So-Called Disaster | 
| Paul Rivers in 21 Grams | 
| Jimmy Markum in Mystic River | 
| Samuel J. Bicke in The Assassination of Richard Nixon | 
| Tobin Keller in The Interpreter | 
| Willie Stark in All the King's Men | 
| Jack in The Tree of Life | 
| Sean Penn in What Just Happened | 
| Joe Wilson in Fair Game | 
| Harvey Milk in Milk | 
| Jack Holden in Licorice Pizza | 
| Mickey Cohen in Gangster Squad | 
| Cheyenne in This Must Be the Place | 
| 16080 in Untitled Dylan Penn/Sean Penn Project | 
| Narrator in The Human Experiment | 
| 16080 in Superpower | 
| Terrier in The Gunman | 
| Dr. William Chester Minor in The Professor and the Madman | 
| 16080 in Daddio | 
| Gene Rutkovsky in Black Flies |