Entertainment

The Best Mary Stuart Masterson Movies 

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Updated September 23, 2019 569 votes 166 voters 10.9k 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.

list ordered by
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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#68 of 803 The Greatest Chick Flicks Ever Made #212 of 599 The Greatest Epic Movies Ever Made

2
Ranker Video
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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#723 of 1,699 The Most Rewatchable Movies #173 of 302 The Greatest Soundtracks of All Time #330 of 571 The Greatest Movies Of The 1980s, Ranked

3
Ranker Video
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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#157 of 803 The Greatest Chick Flicks Ever Made #210 of 460 The Most Quotable Movies of All Time

4
Ranker Video
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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#404 of 803 The Greatest Chick Flicks Ever Made #834 of 1,196 The Absolute Funniest Movies Of All Time

5
Ranker Video
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.
6
Ranker Video
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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#423 of 803 The Greatest Chick Flicks Ever Made #40 of 59 The 30+ Best Modern Western Movies

7
Ranker Video
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
8
Ranker Video
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
9
Ranker Video
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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#285 of 439 The Funniest '80s Movies #20 of 26 The Best Brat Pack Movieslisted on Movies Set in Brooklyn

10
Ranker Video
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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#235 of 265 The Best Ensemble Movies #90 of 113 The Best Screwball Comedies #169 of 179 The Best Mystery Movies

11
Ranker Video
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
12
Ranker Video
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
Ranker Video
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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#352 of 396 The Best Western Movies Ever Made #6 of 41 The Best Movies That Won Razzies

14
Ranker Video
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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#867 of 1,699 The Most Rewatchable Movies #98 of 160 The Best Dystopian And Near Future Movies #44 of 173 Movies That Should Be Made Into Broadway Musicals

15
Ranker Video
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
16
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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
17
Ranker Video
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
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
19
Ranker Video
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
20
Ranker Video
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
21
Ranker Video
Leo Elisabeth Shue, Dennis Hopper, Mary Stuart Masterson

Released: 2002

Directed by: Mehdi Norowzian

Leo is a 2002 drama film directed by Mehdi Norowzian.
22
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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
23
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Lauren Bacall, Anjelica Huston, Robert Mitchum

Released: 1988

Directed by: Danny Huston

Mr. North is a 1988 American comedy-drama film starring Anthony Edwards, based on the 1973 novel Theophilus North by Thornton Wilder. Directed by Danny Huston, the film became a family project; ...more
24
Ranker Video
Mary Stuart Masterson, Anthony LaPaglia, Beau Starr

Released: 1999

Directed by: Paul Shapiro

Black and Blue is a 1999 American made for TV movie. Based on the novel by Anna Quindlen.
25
Ranker Video
Mary Stuart Masterson, Henry Simmons, John Shea

Released: 2007

Directed by: Scott Dacko

When a disillusioned GI, an ex-prostitute and a small-time crook come under the spell of a charismatic, left-wing radical, a terrorist cell emerges in our own backyard.