IMDb Page
Movie Release Date Character Age at Release
In the Grey 01/16/25 44
Road House 03/08/24 Elwood Dalton 43
Guy Ritchie's The Covenant 04/19/23 Master Sergeant John Kinley 42
Strange World 11/23/22 Searcher Clade (voice) 41
Spider-Man: All Roads Lead to No Way Home 05/03/22 Self (archive footage) 41
Ambulance 03/16/22 Danny Sharp 41
Spider-Man: No Way Home 12/15/21 Mysterio / Quentin Beck (archive footage) (uncredited) 40
The Guilty 09/24/21 Joe Baylor 40
Spirit Untamed 05/20/21 Jim Prescott (voice) 40
One Night Only: The Best of Broadway 12/11/20 Self 39
The Great Work Begins: Scenes from Angels in America 10/08/20 Himself 39
Take Me to the World: A Sondheim 90th Birthday Celebration 04/26/20 Self - Performer 39
John Mulaney & The Sack Lunch Bunch 12/24/19 Mr. Music 39
Spider-Man: Far From Home 06/28/19 Quentin Beck / Mysterio 38
Velvet Buzzsaw 02/01/19 Morf Vandewalt 38
Wildlife 09/23/18 Jerry Brinson 37
The Sisters Brothers 09/19/18 John Morris 37
Great Performers: Horror Show 12/07/17 The Damned 36
Stronger 09/22/17 Jeff Bauman 36
Okja 06/28/17 Dr. Johnny Wilcox 36
Life 03/22/17 Dr. David Jordan 36
Deus ex Machina: The Philosophy of 'Donnie Darko' 12/12/16 Self 35
Nocturnal Animals 11/04/16 Edward Sheffield / Tony Hastings 35
Everest 09/10/15 Scott Fischer 34
Demolition 04/08/15 Davis Mitchell 34
Southpaw 03/24/15 Billy 'The Great' Hope 34
Accidental Love 02/10/15 Howard Birdwell 34
Nightcrawler 10/23/14 Louis Bloom 33
Lucid Dreams: The Making of Enemy 06/24/14 Self 33
Enemy 03/14/14 Adam Bell / Anthony Claire 33
Prisoners 09/19/13 Detective Loki 32
End of Watch 09/20/12 Brian Taylor 31
The Shoes: Time to Dance 03/12/12 31
Source Code 03/30/11 Colter Stevens 30
Love & Other Drugs 11/04/10 Jamie Randall 29
Prince of Persia: The Sands of Time 05/19/10 Prince Dastan 29
Jake Gyllenhaal Challenges the Winner of the Nobel Peace Prize 01/01/10 Donnie Darko / Anthony Swafford (archive footage) 29
Brothers 12/02/09 Tommy Cahill 28
Heath Ledger: A Tribute 06/01/09 Self 28
Saturday Night Live: The Best of Amy Poehler 04/18/09 Frank O'Connor (archive footage) 28
Rendition 09/07/07 Douglas Freeman 26
Zodiac 03/02/07 Robert Graysmith 26
Jarhead 11/04/05 Anthony Swofford 24
Brokeback Mountain 09/10/05 Jack Twist 24
Proof 09/05/05 Harold 'Hal' Dobbs 24
Jiminy Glick in Lalawood 05/08/05 Jake Gyllenhaal 24
The Man Who Walked Between the Towers 04/23/05 24
Donnie Darko: Production Diary 10/04/04 Self 23
The Day After Tomorrow 05/26/04 Sam Hall 23
Abby Singer 10/28/03 Self (uncredited) 22
Moonlight Mile 09/09/02 Joe Nast 21
Highway 03/26/02 Pilot Kelson 21
The Good Girl 01/12/02 Holden Worther 21
Lovely & Amazing 08/31/01 Jordan 20
Bubble Boy 08/24/01 Jimmy Livingston 20
Donnie Darko 01/19/01 Donnie Darko 20
October Sky 02/19/99 Homer Hickam 18
Homegrown 04/17/98 Jake 17
Josh and S.A.M. 11/24/93 Leon Coleman 12
A Dangerous Woman 09/10/93 Edward 12
City Slickers 06/07/91 Danny Robbins 10
Francis and The Godfather None Robert Evans 43
Oblivion Song None Nathan Cole 43
Prophet None John Prophet 43
Cut and Run None 43
The Anarchists vs ISIS None 43
Snow Blind None 43
The Division None 43
Rio None 43