Entertainment

The Best Denis Leary Movies 

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Updated September 23, 2019 835 votes 166 voters 19.9k views 49 items

List Rules Vote for your favorite movies, regardless of critic reviews or how big the role was.

List of the best Denis Leary movies, ranked best to worst with movie trailers when available. Denis Leary's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Denis Leary movies is decided by how many votes they receive, so only highly rated Denis Leary movies will be at the top of the list. Denis Leary has been in a lot of films, so people often debate each other over what the greatest Denis Leary movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Denis Leary films to end the squabble once and for all.

If you think the best Denis Leary role isn't at the top, then upvote it so it has the chance to become number one. The greatest Denis Leary performances didn't necessarily come from the best movies, but in most cases they go hand in hand.

The list you're viewing is made up of a variety of different films, including Wag the Dog and Ice Age.

"This list answers the questions, "What are the best Denis Leary movies?" and "What are the greatest Denis Leary roles of all time?"

Notable directors that have worked with Denis Leary include names like M. Night Shyamalan, John Fortenberry and Clint Eastwood. Is Denis Leary your favorite person to watch on the big screen? You might also want to vote on our best Anjelica Huston and Christian Slater films lists too.

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1
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Kevin Spacey, J.K. Simmons, Denis Leary

Released: 1994

Directed by: Ted Demme

The Ref is a 1994 American black comedy film directed by Ted Demme, produced by Don Simpson and Jerry Bruckheimer and starring Denis Leary, Judy Davis, and Kevin Spacey.

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#648 of 1,009 The All-Time Greatest Comedy Films #222 of 493 The Funniest '90s Movies #79 of 109 The Best Christmas Movies of All Time

2
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James Earl Jones, Denis Leary, Karen Allen

Released: 1993

Directed by: David M. Evans

The Sandlot, also known as The Sandlot Kids, is a 1993 American coming-of-age film Comedy directed by David M. Evans, which tells the story of a group of young baseball players during the summer ...more

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#87 of 1,699 The Most Rewatchable Movies #131 of 1,009 The All-Time Greatest Comedy Films What Ever Happened To All The Kids From The Sandlot?

3
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Jack Black, Ray Romano, Jane Krakowski

Released: 2002

Directed by: Chris Wedge, Carlos Saldanha

Ice Age is a 2002 American computer-animated comedy adventure film directed by Carlos Saldanha and Chris Wedge from a story by Michael J. Wilson. It was produced by Blue Sky Studios and ...more

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#42 of 590 The Best Animated Films Ever #161 of 1,009 The All-Time Greatest Comedy Films The Best Characters in the Ice Age Series, Ranked

4
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Kirsten Dunst, Robert De Niro, Dustin Hoffman

Released: 1997

Directed by: Barry Levinson

Wag the Dog is a 1997 black comedy film produced and directed by Barry Levinson. The screenplay by Hilary Henkin and David Mamet was loosely adapted from Larry Beinhart's novel American Hero. ...more

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#259 of 493 The Funniest '90s Movies #5 of 54 The Funniest Comedy Movies About Politics

5
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Cuba Gooding Jr., Jeremy Piven, Emilio Estevez

Released: 1993

Directed by: Stephen Hopkins

Judgment Night is a 1993 action thriller film directed by Stephen Hopkins and starring Emilio Estevez, Cuba Gooding Jr., Jeremy Piven and Stephen Dorff as a group of friends on the run from a ...more
6
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Hayden Panettiere, Ashley Tisdale, Kevin Spacey

Released: 1998

Directed by: John Lasseter, Andrew Stanton

A Bug's Life is a 1998 American computer-animated comedy adventure film produced by Pixar Animation Studios and released by Walt Disney Pictures. Directed by John Lasseter and co-directed by ...more

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#32 of 590 The Best Animated Films Ever #548 of 1,196 The Absolute Funniest Movies Of All Timelisted on The Highest Grossing 90s Movies

7
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Sandra Bullock, Sylvester Stallone, Jack Black

Released: 1993

Directed by: Marco Brambilla

Demolition Man is a 1993 American science fiction action film directed by Marco Brambilla in his directorial debut. The film stars Sylvester Stallone and Wesley Snipes. The film was released in ...more

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#440 of 460 The Most Quotable Movies of All Time #196 of 302 The Greatest Soundtracks of All Time Demolition Man Remains One Of The Most Underrated Movies Of The '90s

8
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Christopher Walken, Denis Leary, Jay Mohr

Released: 1997

Directed by: Peter O'Fallon

This film is a 1997 American action comedy film, starring Christopher Walken as a boss, Denis Leary as his driver, and Sean Patrick Flanery, Johnny Galecki, Jay Mohr, Jeremy Sisto, and Henry ...more
9
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Andrew Garfield, Emma Stone, Rhys Ifans

Released: 2012

Directed by: Marc Webb

The Amazing Spider-Man is a 2012 American superhero film directed by Marc Webb, based on the Marvel Comics character. After Peter Parker (Andrew Garfield) is bitten by a genetically altered ...more

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#56 of 165 The Greatest Comic Book Movies of All Time #41 of 184 The Best Superhero Movies Ever Made

10
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Sarah Michelle Gellar, Kirsten Dunst, Christina Ricci

Released: 1998

Directed by: Joe Dante

Small Soldiers is a 1998 American science fiction action film directed by Joe Dante. The film revolves around two adolescents, who get caught in the middle of a battle between two factions of ...more

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#195 of 624 The Greatest Guilty Pleasure Movies #478 of 590 The Best Animated Films Ever ‘Small Soldiers’ Is Way, Way Darker Than You Remember

11
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Pierce Brosnan, Faye Dunaway, Rene Russo

Released: 1999

Directed by: John McTiernan

The Thomas Crown Affair is a 1999 American film directed by John McTiernan. The film, starring Pierce Brosnan, Rene Russo and Denis Leary, is a remake of the 1968 film of the same name. The film ...more

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#1,290 of 1,699 The Most Rewatchable Movies #28 of 34 Romantic Movies You Can Trick Your BF Into Watchinglisted on Every Oscar Winning Film Ever

12
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Queen Latifah, Kristen Wiig, Jane Lynch

Released: 2009

Directed by: Carlos Saldanha, Mike Thurmeier

Ice Age: Dawn of the Dinosaurs is a 2009 American 3-D computer animated comedy adventure film, and the third installment in the Ice Age series. It was produced by Blue Sky Studios and ...more

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#195 of 219 The Worst Sequels Of All Time #682 of 1,009 The All-Time Greatest Comedy Films The Best Characters in the Ice Age Series, Ranked

13
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Famke Janssen, Martin Sheen, Billy Crudup

Released: 1998

Directed by: Ted Demme

Monument Ave., originally titled Snitch in the USA and titled Noose in Australia, is a 1998 American crime comedy-drama film directed by Ted Demme and starring Denis Leary. The film takes place ...more
14
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Queen Latifah, Jay Leno, Ariel Winter

Released: 2006

Directed by: Carlos Saldanha

Ice Age: The Meltdown is a 2006 American computer-animated comedy adventure film. It is a sequel to the 2002 computer-animated film Ice Age. It was produced by Blue Sky Studios for 20th Century ...more

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#394 of 1,699 The Most Rewatchable Movies #535 of 1,009 The All-Time Greatest Comedy Films The Best Characters in the Ice Age Series, Ranked

15
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Clint Eastwood, Lucy Liu, James Woods

Released: 1999

Directed by: Clint Eastwood

True Crime is a 1999 American mystery drama film directed by Clint Eastwood, and based on Andrew Klavan's 1995 novel of the same name. Eastwood also stars in the film as a journalist covering ...more
16
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Sandra Bullock, Denis Leary, Yaphet Kotto

Released: 1996

Directed by: Bill Bennett

Two If by Sea is a 1996 romantic comedy film directed by Bill Bennett, and starring Sandra Bullock and Denis Leary. The screenplay, written by Leary and Mike Armstrong, is based on a story by ...more
17
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Ray Liotta, Danny Glover, Denis Leary

Released: 1995

Directed by: Simon Wincer

Operation Dumbo Drop is a 1995 American comedy film directed by Simon Wincer that explores politics, and animal welfare. The storyline was conceived from a screenplay written by Gene Quintano ...more
18
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Elizabeth Hurley, Steve Buscemi, Denis Leary

Released: 2001

Directed by: Tom DiCillo

Double Whammy is a 2001 comedy/drama film. Although intended to be released in theaters, it was ultimately distributed direct-to-video.
19
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Rosie O'Donnell, Julia Stiles, Dana Delany

Released: 1998

Directed by: M. Night Shyamalan

Wide Awake is a 1998 comedy-drama film written and directed by M. Night Shyamalan and produced by Cathy Konrad and Cary Woods. The film stars Denis Leary, Dana Delany, Joseph Cross and Rosie ...more
20
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Ice Age: A Mammoth Christmas Queen Latifah, Ray Romano, Denis Leary

Released: 2011

Directed by: Karen Disher

TV appearance Thursday in “A Mammoth Christmas” (Fox, 8 p.m.), a holiday special that doubles as an early promotion for “Ice Age: Continental Drift,” which will hit theaters on July 13, 2012.
21
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Jennifer Lopez, Nicki Minaj, Drake

Released: 2012

Directed by: Steve Martino, Mike Thurmeier

Ice Age: Continental Drift is a 2012 American 3D computer-animated comedy adventure film directed by Steve Martino and Mike Thurmeier. It was written by Jason Fuchs and Michael Berg, and ...more

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#148 of 590 The Best Animated Films Ever #832 of 1,009 The All-Time Greatest Comedy Films The Best Characters in the Ice Age Series, Ranked

22
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Ice-T, Terrence Howard, Bernie Mac

Released: 1993

Directed by: Ted Demme

Who's the Man? is a 1993 thriller comedy film, directed by Ted Demme, in his feature film directing debut. The film stars Yo! MTV Raps hosts Doctor Dré and Ed Lover as its two main ...more
23
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Anne Heche, Sam Rockwell, Denis Leary

Released: 1997

Directed by: Julie Dash, Jonathan Demme, Bob Balaban, Abel Ferrara, Ted Demme, + more

Subway Stories: Tales from the Underground is a film made in 1997 and produced by Home Box Office for television. It began as a contest among New Yorkers who submitted stories about their ...more
24
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Traci Lords, Denis Leary, Annabella Sciorra

Released: 1997

Directed by: Roger Christian

Underworld is a 1997 comedy thriller film that was directed by Roger Christian and stars Denis Leary, Joe Mantegna and Annabella Sciorra.
25
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Patrick Stewart, Denis Leary, Mario Van Peebles

Released: 1994

Directed by: Deran Sarafian

Gunmen is a 1994 action-comedy film directed by Deran Sarafian. It stars Mario Van Peebles, Christopher Lambert, Denis Leary, Kadeem Hardison and Patrick Stewart. Robert Harper and Brenda Bakke ...more