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Best Mary Stuart Masterson Performances, Ranked

Mary Stuart Masterson made her acting debut before the age of 10 with a part in her father Peter Masterson’s film The Stepford Wives. From there, Masterson would move on to various projects and become a defining actor of the ’80s and ’90s with roles in films such as Some Kind of Wonderful, Immediate Family, Fried Green Tomatoes, and Benny and Joon.

Mary Stuart Masterson has over 50 acting credits, with many leading roles making it hard to summarize the brilliance and diversity of Mastertson as an actor. However, we have picked out the best Mary Stuart Masterson performances for you below.

15 Daniel Isn’t Real

Samuel Goldwyn Films

Daniel Isn’t Real is a 2009 psychological horror film that follows a troubled college student Luke (Miles Robbins), who brings back his imaginary friend Daniel (Patrick Schwarzenegger), to help deal with his trauma. As the two grow closer, Daniel becomes jealous of other friendships and relationships, pushing Luke to commit violent acts.

Almost always the leading lady, Mary Stuart Masterson’s role as Claire, Luke’s mother and one of Daniel’s targets, was a welcome supporting role in the edgy horror film that melded elements of cosmic, body, and psychological horror. This also marks one of the few horror productions that Masterson was involved in, making it a notable performance outside the actors’ regular roles.

14 Bad Girls

Cast of Bad Girls
20th Century Fox

Bad Girls follows four former prostitutes turned outlaws and had notable names in the cast, including Madeleine Stowe, Andie MacDowell, and Drew Barrymore. Masterson played one of the outlaws in Anita Crown. Despite its star-studded cast Bad Girls was a dud on release, bombing at the box office and given negative reviews from critics and audiences alike.

While the film’s failures are chopped up more to scripting than casting, this is Masterson’s weakest marquee credit which is only noteworthy by seeing her work alongside other prominent actresses of the era.

13 West of Here

West of Here Poster
Image Entertainment

The Masterson family has been working in Hollywood for generations, with Mary’s father Peter Masterson, giving the young actor her first role with a small part in his film The Stepford Wives. So it was no surprise that when Mary’s brother Peter (named after his father) decided to try his hand at filmmaking that she would show support.

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Unfortunately, West of Here would show all the signs of a first-time filmmaker over his head, with the tale of a man heading on the road to find himself offering little new and rough around the edges. Still, Mary Stuart Masterson shines in her role as Genevieve, the romantic interest to lead Josiah (Norbert Leo Butz), and manages to be the major highlight of the production. This one is for the purists, as the film is hard to recommend outside of Masterson’s performance.

12 Mad at the Moon

Mary Stuart Masterson Mad at the Moon
Republic Pictures Home Video

Perhaps Masterson’s limited horror performances stem from her role as Jenny Lee in the Western/romance/horror movie Mad at the Moon. In one review by Variety, the film was called a “bad attack of miscasting” after a showing at Cannes. The story is also a jumble of genres that do not work well within the Western genre, and Masterson and co-star Hart Bochner could not build up the needed chemistry.

Still, Masterson is a true beauty in Mad at the Moon, and the film is technically well executed, giving the actor these picturesque moments under the solid visuals and sweeping score. This may be one of the more forgotten performances from Masterson, but it is not without appeal and is worth a watch for fans.

11 Radioland Murders

Mary Stuart Masterson Radioland Murders
Universal Pictures

The critically maligned Radioland Murders paid homage to radio plays of the ’30s with a mix of comedy and murder mystery taking place in a radio station. With an ensemble cast, critics felt that the film was too focused on slapstick humor and failed to develop any characters, ensuring most of the comedy fell flat.

However, the film found more of a fan base among the audience, who was a bit more forgiving, and Mary Stuart Masterson’s role as Penny, secretary and estranged wife to lead Roger Henderson (Brian Benben). The enjoyment a viewer gets from Radioland Murders will depend heavily on their taste in comedies — it is certainly not among the best comedies of the ’90s. Regardless, this is one of Masterson’s more entertaining roles, as the actor got to flex her comedic chops alongside many comedic greats.

10 Digging to China

Mary Stuart Masterson Digging to China
Moonstone Entertainment

A film that would also mark the first starring role of a young Evan Rachel Wood, Digging to China is a sincere and unpretentious indie film that follows one girl’s friendship with an intellectually challenged adult in Ricky Schroth (Kevin Bacon). The coming-of-age film was met with mixed reviews on release, but the amount of insight and considered approach towards the subject makes Digging to China a worthwhile watch.

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Here Mary Stuart Masterson plays Gwen, the older sister of Wood’s character. Outgoing and known for her propensity towards dating as much as possible, Masterson brought a lot of life and sentimentality to the role, capturing the family dynamic between sisters in both its positives and complexities.

9 Heaven Help Us

Mary Stuart Masterson Heaven Help Us
Tri-Star Pictures

The earliest film to be included in this list saw a young Masterson playing the role of Danni, a young catholic girl who runs a soda shop at her school, which acts as a haven for young kids to come and speak freely and smoke. Also playing the role of the girlfriend of the central character Dunn (Andrew McCarthy), Masterson’s performance was integral in adding depth to the comedy that explored themes of love and the struggles of youth in the catholic school system.

Heaven Help Us is a sweet and shy romance tale, with Masterson and McCarthy being the story’s central focus. This is a hidden gem within Masterson’s career and one that is certainly worth seeking out for those interested in exploring the actor’s beginnings in the movie industry.

8 At Close Range

Mary Stuart Masterson & Sean Penn At Close Range
Orion Pictures

This neo-noir crime drama At Close Range saw a young Masterson working with two film icons in Sean Penn and Christopher Walken. The plot follows Brad Whitewood Jr., played by Sean Penn, who falls in love with a 16-year-old Terry (Masterson) and attempts to run away with her. Christopher Walken plays the fatherly role, which is at the crux of the drama as the movie explores the family’s transgressions with a gritty, violent realism.

This is one of Masterson’s earlier defining roles, and it was apparent how she held her own with many iconic in the film industry is the perfect precursor to understanding her forward trajectory.

7 The Book of Stars

The Book of Stars Poster
Winstar Home Video

One of the most difficult entries in this list as to subject, while also being a testament to Masterson’s willingness to take on challenging roles, The Book of Stars revolves around two orphaned sisters, Mary and Penny, impoverished and struggling to find peace. Masterson plays Penny, who turns to prostitution to support her sister Penny (Jena Malone), who suffers from cystic fibrosis.

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Tucked away in Masterson’s filmography, this film is worth tracking down, regardless of the uncomfortable themes it explores. Masterson’s performance and handling of heavy content show the actor at her most accomplished and considered.

6 Bed of Roses

Mary Stuart Masterson & Christian Slater Bed of Roses
New Line Cinema

Masterson has had her fair share of leading roles in romance films across from some of the biggest stars. While her most notable romance may have come from Benny and Joon, Bed of Roses matches her with Christian Slater in the story of a business executive falling in love with a floral shop owner.

Here Masterson gives a memorable performance as Lisa Walker, a strong independent woman whose past trauma has left her closed off to the idea of love, only to be drawn to a shy florist, Lewis, who allows her to open up and deal with past traumas finally. Exploring vulnerability and the struggles of personal growth, Bed of Roses is a heartfelt romance story worthy of a watch or revisit.

Immediate Family Poster
Columbia Pictures

In what would mark the actor’s first award for Best Supporting Actress from the National Board of Review of Motion Pictures, Masterson plays Lucy, a pregnant mother who later regrets her decision to offer up her child for adoption. Immediate Family navigated the complexities of the adoption process and young motherhood, backed by solid performances from Glenn Close, James Wood, and Kevin Dillon.

Watching Immediate Family, it is clear why Masterson got a nod for her performances as she handles the role of teenage motherhood with confidence and skill. This is an impressive supporting role and one of Masterson’s best performances during her career in the ’80s.

4 Some Kind of Wonderful

Mary Stuart Masterson Some Kind of Wonderful
Paramount Pictures

Writer and Director John Hughes is responsible for some of the most beloved films of the ’80s and ’90s, having penned the likes of Planes, Trains and Automobiles, The Breakfast Club, and Home Alone, to name only a few. While being a less infamous entry into his oeuvre, Some Kind of Wonderful is one of the best-written films from the iconic scriptwriter, with the New York Times review going as far as calling it a “much-improved, recycled version of the Pretty in Pink story.”

Masterson has the most entertaining role in the film, playing Watts, a street-wise rebellious teenager with a love of music. The performance is noteworthy for Masterson’s ability to portray a playful, feisty character balanced by a sensitive and loving side that made her an endearing love interest to the lead character Keith Nelson, played by Eric Stoltz.

3 Fried Green Tomatoes

Mary Stuart Masterson Friend Green Tomatoes
Universal Pictures

Masterson’s role in Fried Green Tomatoes marks somewhat of a cornerstone for the actor, not just because of the popularity and critical acclaim of the film. Instead, Masterson’s role as a strong-willed and independent woman Idgie Threadgoode, resonated with many viewers, notably sincerity in playing a lesbian.

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While much of the fanfare went to other actors in the film, with Jessica Tandy picking up a Golden Globe and Kathy Bates awarded a BAFTA for their performances, Masterson’s role is integral to the film, and her importance is often understated. This may, arguably, be the best film that Masterson has acted in and is a must-watch for film fans.

2 Isle of Hope

Diane Ladd & Mary Stuart Masterson Isle of Hope
Aventura Entertainment

Isle of Hope is a touching portrait of a family facing the death of a mother and the complexities that can arise from having to come to terms with a troubled past to find solace. Here Masterson plays Victoria, a playwright turned university professor who became estranged from her mother (Diane Ladd), a once famous actor who always spoke out against her desires to be a writer. The film is about their reconciliation as memory loss offers them a clean slate to revisit fond memories.

Seeing Masterson alongside the legendary Diane Ladd is a notable draw to checking out the film, as the two play off each other brilliantly and show the skill of decades of experience in the industry. Moreover, the story is touching and sincere in portraying family issues and facing the harsh reality of death in the family. The film, released in 2022, is a testament to Masterson’s staying power as an actress and is easily her best modern performance.

1 Benny & Joon

Benny & Joon (1993)

Masterson’s most iconic role came via the 1993 rom-com film Benny & Joon, where she played the titular Joon, an artist struggling with mental health issues. This was considered a challenging role for Masterson, but she brought reverence to the part along with endearing comedic wit.

The film also paired up with Johnny Depp, who played Sam, a young man who falls in love with Joon despite her eccentricities and struggles. Benny & Joon is Mary Stuart Masterson’s best performance and an essential watch.

This story originally appeared on Movieweb

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