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The Best Mary Stuart Masterson Movies 

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Updated September 23, 2019 572 votes 168 voters 11k views 32 items

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

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

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

List includes Benny & Joon, At Close Range, more.

"This list answers the questions, "What are the best Mary Stuart Masterson movies?" and "What are the greatest Mary Stuart Masterson roles of all time?"

Movie fans who love Mary Stuart Masterson have also been known to enjoy films starring Lea Thompson and Jami Gertz.

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1
Ranker Video
Kathy Bates, Mary-Louise Parker, Chris O'Donnell

Released: 1991

Directed by: Jon Avnet

Fried Green Tomatoes is a 1991 comedy-drama film based on the novel Fried Green Tomatoes at the Whistle Stop Cafe. Directed by Jon Avnet. It tells the story of a Depression-era friendship ...more

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#157 of 599 The Greatest Epic Movies Ever Made #277 of 1,699 The Most Rewatchable Movies #60 of 804 The Greatest Chick Flicks Ever Made

2
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Lea Thompson, Candace Cameron-Bure, Mary Stuart Masterson

Released: 1987

Directed by: Howard Deutch

Some Kind of Wonderful is a 1987 American romance film starring Eric Stoltz, Mary Stuart Masterson, and Lea Thompson. It is one of the several successful teen dramas written by John Hughes in ...more

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#233 of 571 The Greatest Movies Of The 1980s, Ranked #599 of 1,699 The Most Rewatchable Movies #238 of 804 The Greatest Chick Flicks Ever Made

3
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Johnny Depp, Julianne Moore, William H. Macy

Released: 1993

Directed by: Jeremiah S. Chechik

Benny & Joon is a 1993 romantic comedy film released by Metro-Goldwyn-Mayer about how two eccentric individuals, Sam and Juniper "Joon", find each other and fall in love. Aidan ...more

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#132 of 493 The Funniest '90s Movies #512 of 1,699 The Most Rewatchable Movies #179 of 804 The Greatest Chick Flicks Ever Made

4
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Robert Downey Jr., Cybill Shepherd, Mary Stuart Masterson

Released: 1989

Directed by: Emile Ardolino

Chances Are is a 1989 romantic comedy film directed by Emile Ardolino and starring Cybill Shepherd, Robert Downey, Jr., Ryan O'Neal, and Mary Stuart Masterson. The original music score was ...more

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#365 of 571 The Greatest Movies Of The 1980s, Ranked #875 of 1,208 The Absolute Funniest Movies Of All Time #789 of 1,027 The All-Time Greatest Comedy Films

5
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Josh Brolin, Christian Slater, Gina Torres

Released: 1996

Directed by: Michael Goldenberg

Bed of Roses is a 1996 romance film that starred Mary Stuart Masterson and Christian Slater. It was written and directed by Michael Goldenberg.
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Drew Barrymore, Andie MacDowell, Madeleine Stowe

Released: 1994

Directed by: Jonathan Kaplan

Bad Girls is a 1994 western film starring Madeleine Stowe, Mary Stuart Masterson, Andie MacDowell and Drew Barrymore. It was directed by Jonathan Kaplan from a screenplay by Ken Friedman and ...more

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#228 of 395 The Best Western Movies Ever Made #378 of 804 The Greatest Chick Flicks Ever Made #42 of 62 The 30+ Best Modern Western Movies

7
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James Earl Jones, James Caan, Laurence Fishburne

Released: 1987

Directed by: Francis Ford Coppola

Gardens of Stone is a 1987 American drama film directed by Francis Coppola, based on the novel of the same title by Nicholas Proffitt. It stars James Caan, Anjelica Huston, James Earl Jones and ...more

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#61 of 76 The Best Laurence Fishburne Movies #99 of 204 The Best R-Rated War Movies

8
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Patrick Dempsey, Donald Sutherland, Mary Stuart Masterson

Released: 1985

Directed by: Michael Dinner

Heaven Help Us is a 1985 comedy-drama film starring Andrew McCarthy, Mary Stuart Masterson, Kevin Dillon, Donald Sutherland, Wallace Shawn, Stephen Geoffreys, John Heard, and Patrick Dempsey.

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#318 of 439 The Funniest '80s Movies #437 of 460 The Most Quotable Movies of All Timelisted on Movies Set in Brooklyn

9
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Glenn Close, James Woods, Mary Stuart Masterson

Released: 1989

Directed by: Jonathan Kaplan

Immediate Family is a 1989 drama film directed by Jonathan Kaplan. It stars Glenn Close and James Woods as a married childless couple who want a baby. They decide to adopt from a pregnant ...more
10
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Christopher Lloyd, Mary Stuart Masterson, George Burns

Released: 1994

Directed by: Charles Martin Smith, Mel Smith

This film is a 1994 comedy mystery film directed by Mel Smith and co-written/produced by George Lucas. This movie is set in the 1939 atmosphere of old-time radio and pays homage to the screwball ...more

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#468 of 493 The Funniest '90s Movies #253 of 266 The Best Ensemble Movies #159 of 182 The Best Mystery Movies

11
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Kevin Costner, Tom Petty, Mary Stuart Masterson

Released: 1997

Directed by: Kevin Costner

The Postman is a 1997 American epic post-apocalyptic adventure film. It is directed by, produced by, and stars Kevin Costner, with the screenplay written by Eric Roth and Brian Helgeland, based ...more

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#218 of 395 The Best Western Movies Ever Made #435 of 599 The Greatest Epic Movies Ever Made #72 of 161 The Best Dystopian And Near Future Movies

12
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Evan Rachel Wood, Kevin Bacon, Mary Stuart Masterson

Released: 1998

Directed by: Timothy Hutton

Digging to China is a 1998 American drama film that marked the directorial debut of actor Timothy Hutton and the screen debut of Evan Rachel Wood. The screenplay by Karen Janszen focuses on the ...more
13
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Sean Penn, Christopher Walken, Kiefer Sutherland

Released: 1986

Directed by: James Foley

At Close Range is a 1986 crime drama film directed by James Foley, based on the real life rural Pennsylvania crime family led by Bruce Johnston, Sr. which operated during the 1960s and 1970s. It ...more
14
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Tina Louise, Mary Stuart Masterson, Katharine Ross

Released: 1975

Directed by: Bryan Forbes

The Stepford Wives is a 1975 science fiction–thriller film based on the 1972 Ira Levin novel of the same name. It was directed by Bryan Forbes with a screenplay by William Goldman, and stars ...more

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#1,334 of 1,699 The Most Rewatchable Movies #356 of 804 The Greatest Chick Flicks Ever Made #135 of 161 The Best Dystopian And Near Future Movies

15
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Jena Malone, Mary Stuart Masterson, Delroy Lindo

Released: 2000

Directed by: Michael Miner

The Book of Stars is a 1999 American drama film about two sisters, both of whom are on the down slopes of their lives but in entirely different ways. It received its world premiere as part of ...more
16
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Alec Baldwin, Teri Hatcher, Mary Stuart Masterson

Released: 1996

Directed by: Phil Joanou

Heaven's Prisoners is a 1996 American drama crime thriller film directed by Phil Joanou and starring Alec Baldwin, Kelly Lynch, Mary Stuart Masterson, Teri Hatcher and Eric Roberts. It is based ...more

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#179 of 182 The Best Slasher Movies #352 of 377 The Greatest Suspense Movies #18 of 78 The Best Alec Baldwin Movies

17
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Mark Ruffalo, Mary Stuart Masterson, David Hewlett

Released: 1997

Directed by: James Frawley

On the 2nd Day of Christmas is a Lifetime television movie starring Mary Stuart Masterson and Mark Ruffalo, directed by James Frawley.
18
Ranker Video
Three Blind Mice Mary Stuart Masterson, Brian Dennehy, Rosalind Chao

Released: 2008

Directed by: Christopher Leitch

A lawyer defends a man he's known since serving together in Vietnam, who has been accused of murdering three Vietnamese immigrants.
19
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Jon Favreau filmography, Shawnee Smith, Mary Stuart Masterson

Released: 1997

Directed by: George Hickenlooper

Dogtown is a 1997 drama film by George Hickenlooper about life in the small Missouri town of Cuba, Missouri starring Mary Stuart Masterson, Jon Favreau, Rory Cochrane, Harold Russell, and ...more
20
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Gabrielle Union, Alan Rickman, Mos Def

Released: 2004

Directed by: Joseph Sargent

Something the Lord Made is a 2004 film about the black cardiac pioneer Vivien Thomas and his complex and volatile partnership with white surgeon Alfred Blalock, the world famous "Blue Baby ...more
21
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Elisabeth Moss, Mary Stuart Masterson, Tate Donovan

Released: 2002

Directed by: Peter Masterson

West of Here is a 2002 drama film directed by Peter Masterson. Ignoring his father's disapproval, Gil Blackwell (Josh Hamilton) leaves his monotonous business life in Boston for California.
22
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Cybill Shepherd, Stockard Channing, Mary Stuart Masterson

Released: 1993

Directed by: Arthur Hiller

Married to It is a 1991 film directed by Arthur Hiller about three New York City couples with disparate careers, ages, and lifestyles who nonetheless bond through their mutual connection to a ...more
23
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Tom Sizemore, Jim Belushi, Mary Stuart Masterson

Released: 1999

Directed by: Nick Stagliano

The Florentine is a 1999 film directed Nick Stagliano and produced by Francis Ford Coppola's American Zoetrope. It stars Jeremy Davies, Virginia Madsen, Luke Perry, Mary Stuart Masterson, ...more
24
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Jennifer Lopez, James Earl Jones, Mary Stuart Masterson

Released: 1987

Directed by: Connie Kaiserman

My Little Girl is a 1986 American drama film the directorial debut of Connie Kaiserman that was released in the U.S. in 1987. It is also Geraldine Page's final role and Jennifer Lopez' film
25
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Elizabeth Banks, Maria Bello, Chris O'Donnell

Released: 2005

Directed by: Arthur Allan Seidelman

The Sisters is a 2005 film starring Maria Bello, Mary Stuart Masterson, and Erika Christensen as the title characters; it also stars Alessandro Nivola, Rip Torn, Eric McCormack, Steven Culp, ...more