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The Best Rosie O'Donnell Movies 

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Updated June 11, 2019 420 votes 144 voters 18.2k views 22 items

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

List of the best Rosie O'Donnell movies, ranked best to worst with movie trailers when available. Rosie O'Donnell'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 Rosie O'Donnell movies is decided by how many votes they receive, so only highly rated Rosie O'Donnell movies will be at the top of the list. Rosie O'Donnell has been in a lot of films, so people often debate each other over what the greatest Rosie O'Donnell movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Rosie O'Donnell films to end the squabble once and for all.

If you think the best Rosie O'Donnell role isn't at the top, then upvote it so it has the chance to become number one. The greatest Rosie O'Donnell 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 many different films, like Harriet the Spy and Tarzan.

"This list answers the questions, "What are the best Rosie O'Donnell movies?" and "What are the greatest Rosie O'Donnell roles of all time?"

M. Night Shyamalan and Garry Marshall are among those who have directed Rosie O'Donnell at one point or another during their careers in the film industry.

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1
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Madonna, Tom Hanks, Rosie O'Donnell

Released: 1992

Directed by: Penny Marshall

A League of Their Own is a 1992 American comedy-drama film that tells a fictionalized account of the real-life All-American Girls Professional Baseball League. Directed by Penny Marshall, the ...more

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#100 of 599 The Greatest Epic Movies Ever Made #40 of 493 The Funniest '90s Movies #300 of 1,699 The Most Rewatchable Movies

2
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Demi Moore, Christina Ricci, Rosie O'Donnell

Released: 1995

Directed by: Lesli Linka Glatter

Now and Then is a 1995 American coming-of-age film directed by Lesli Linka Glatter and starring Christina Ricci, Rosie O'Donnell, Thora Birch, Melanie Griffith, Gaby Hoffmann, Demi Moore, ...more

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#198 of 349 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #201 of 493 The Funniest '90s Movies #1,266 of 1,699 The Most Rewatchable Movies

3
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Rosie O'Donnell, Glenn Close, Minnie Driver

Released: 1999

Directed by: Kevin Lima, Chris Buck

Tarzan is a 1999 American animated adventure musical film produced by Walt Disney Feature Animation and released by Walt Disney Pictures. The 37th film in the Walt Disney Animated Classics, it ...more

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Every Song in Tarzan, Ranked by Singability #223 of 377 The Best Musical Movies of All Timelisted on Every Oscar Winning Film Ever

4
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Tom Hanks, Meg Ryan, Rosie O'Donnell

Released: 1993

Directed by: Nora Ephron

Sleepless in Seattle is a 1993 American romantic comedy-drama film directed and co-written by Nora Ephron. Based on a story by Jeff Arch, it stars Tom Hanks as Sam Baldwin and Meg Ryan as Annie

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The Most Memorable 'Sleepless in Seattle' Quotes #103 of 349 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #199 of 493 The Funniest '90s Movies

5
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Halle Berry, Elizabeth Taylor, Rosie O'Donnell

Released: 1994

Directed by: Brian Levant

The Flintstones is a 1994 American buddy comedy film directed by Brian Levant and written by Tom S. Parker, Jim Jennewein and Steven E. de Souza. A live-action adaptation of the 1960s animated ...more

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#9 of 24 Movies You Loved As a Child That Just Don't Hold Up #168 of 302 The Greatest Soundtracks of All Time #61 of 140 The Most Rewatchable Comedy Movies

6
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Kristen Stewart, Rosie O'Donnell, Joan Collins

Released: 2000

Directed by: Brian Levant

The Flintstones in Viva Rock Vegas is a 2000 American family-romantic comedy film and prequel to 1994's The Flintstones based on the 1960-66 cartoon series of the same name. Produced by Amblin ...more

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#341 of 377 The Best Musical Movies of All Time #25 of 233 The Worst Sequels Of All Time #6 of 22 The Worst Live-Action Movies Based on Cartoons

7
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Rosie O'Donnell, Madeleine Stowe, Richard Dreyfuss

Released: 1993

Directed by: John Badham

Another Stakeout is a 1993 action comedy film starring Richard Dreyfuss, Emilio Estevez and Rosie O'Donnell. It is a sequel to the 1987 film, Stakeout. Unlike its predecessor, the film was ...more
8
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Rosie O'Donnell, Michelle Trachtenberg, Danny Glover

Released: 1996

Directed by: Bronwen Hughes

Harriet the Spy is a 1996 film adaptation of the 1964 novel of the same name by Louise Fitzhugh, and starring Michelle Trachtenberg as the title character. This film was directed by Bronwen ...more

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#292 of 493 The Funniest '90s Movies #367 of 410 The Best Rainy Day Movies #18 of 24 Great Mystery Movies the Whole Family Will Enjoy

9
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Rosie O'Donnell, Dan Aykroyd, Dana Delany

Released: 1994

Directed by: Garry Marshall

Exit to Eden is a 1994 American comedy-thriller film directed by Garry Marshall and adapted to the screen by Deborah Amelon and Bob Brunner from Anne Rampling's novel of the same name. The ...more

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#119 of 140 The Most Awkward Movies to Watch with Your Parents #54 of 119 The Best R-Rated Sex Comedies #64 of 106 The Best Detective Fiction Movies

10
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Ian McKellen, Rosie O'Donnell, Nick Nolte

Released: 1994

Directed by: James L. Brooks

I'll Do Anything is a 1994 American dramedy film written and directed by James L. Brooks. Its primary plot concerns a down-on-his-luck actor who suddenly finds himself the sole caretaker of his ...more

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#68 of 74 The Best Movies About Parenting #68 of 76 The Best Woody Harrelson Movies #27 of 78 The Best Nick Nolte Movies

11
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Natalie Portman, Uma Thurman, Rosie O'Donnell

Released: 1996

Directed by: Ted Demme

Beautiful Girls is a 1996 American romantic comedy-drama film directed by Ted Demme from a screenplay written by Scott Rosenberg, starring Matt Dillon, Lauren Holly, Timothy Hutton, Rosie ...more
12
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Riding the Bus with My Sister Rosie O'Donnell, Andie MacDowell

Released: 2005

Directed by: Anjelica Huston

Riding the Bus with My Sister is a 2005 film directed by Anjelica Houston.
13
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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

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#156 of 174 The Best Family Drama Movies of All Time #12 of 13 The Best M. Night Shyamalan Movies

14
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The Very Best of America's Funniest Comedians Rosie O'Donnell, Kelsey Grammer, Carrot Top

Released: 2003

15
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Rosie O'Donnell, Andrea Martin, Michael Pitt

Released: 2001

Directed by: John Cameron Mitchell

Hedwig and the Angry Inch is a 2001 American musical comedy-drama film written for the screen and directed by John Cameron Mitchell. Based on Mitchell's and Stephen Trask's stage musical Hedwig ...more

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Every Song in Hedwig and the Angry Inch, Ranked by Singability #132 of 217 Musical Movies With the Best Songs #75 of 347 Movies with the Best Soundtracks

16
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Rosie O'Donnell, David Spade, Barbara Eden

Released: 1996

Directed by: Arlene Sanford

A Very Brady Sequel is a 1996 comedy film and sequel to 1995's The Brady Bunch Movie. Both films are Spoofss to the classic 1969–1974 television sitcom The Brady Bunch. The film was directed by ...more

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#328 of 1,027 The All-Time Greatest Comedy Films #11 of 12 12 Comedy Sequels That Might Actually Be Better Than The Originals #57 of 68 The Best Comedy Movie Sequels

17
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Rosie O'Donnell, Ruby Dee, Raquel Castro

Released: 2009

Directed by: Yves Simoneau

America is a 2009 Lifetime Television film starring Rosie O'Donnell, Ruby Dee and Philip Johnson. It was directed by Yves Simoneau and written by Joyce Eliason. The film is based on the young ...more
18
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Rosie O'Donnell, Kelsey Grammer, Jeff Foxworthy

Released: 2001

19
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The Best of the Improv: Vol. 6 Rosie O'Donnell, Drew Carey, Jeff Foxworthy

Released: 2003

20
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Rosie O'Donnell, Brendan Fraser, Faye Dunaway

Released: 1997

Directed by: Ross Kagan Marks

The Twilight of the Golds is a 1997 television film.
21
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Rosie O'Donnell, Fran Drescher, Jeremy Piven

Released: 1994

Directed by: Bill Fishman

Car 54, Where Are You? is a 1994 comedy film directed by Bill Fishman and stars David Johansen and John C. McGinley. It is based on the television series of the same name starring Joe E. Ross ...more

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#33 of 94 The Worst January Movie Releases #140 of 155 The Greatest Car Movies Ever Made

22
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Rosie O'Donnell, Jane Lynch, Sean Young

Released: 1993

Directed by: Carl Reiner

This film is a 1993 thriller comedy film directed by Carl Reiner. It parodies the erotic thriller movie genre, which at the time had reached its commercial peak. The film stars Armand Assante as ...more