Every Matt Damon Western, Ranked

Summary

• Matt Damon’s diverse career includes impressive Western movie performances showcasing his range and talent.
• Damon’s lesser-known roles in TV and film paved the way for his success, such as The Good Old Boys.
• Spirit: Stallion of the Cimarron highlighted Damon’s voice acting skills in this animated Western classic.

The career of Matt Damon has been categorized by acclaimed roles across a variety of genres and has included some fantastic performances in Western movies. While Damon first became known for his breakout success as the co-writer and star of Good Will Hunting, he’s also portrayed cowboys and Western lawmen on more than one occasion. These enjoyable performances showcased how well Damon was suited to genre movies as he fully embodied the free-roaming ideals and individualist nature of the Wild West.

With many incredible performances under his belt, Damon has made a name for himself through his long-running and Academy Award-winning collaboration with Ben Affleck. However, despite Damon’s success in comedies, dramas, and thrillers, he’s never shied away from tackling complex roles in Western movies. As one of the most recognizable actors working today, Damon’s Western movie output has been an important part of his impressive filmography.

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5 The Good Old Boys (1995)

Matt Damon as Cotton Calloway

The Good Old Boys (1995)

The Good Old Boys is a 1995 Western film directed by and starring Tommy Lee Jones. Set in the early 20th century, it follows the story of Hewey Calloway, a roguish cowboy drifting through the changing landscapes of West Texas. Sissy Spacek, Sam Shepard, and Frances McDormand co-star, portraying characters who grapple with modernity’s encroachment on traditional cowboy life.

Director Tommy Lee Jones Release Date March 5, 1995 Writers Elmer Kelton , Tommy Lee Jones , J.T. Allen Cast Tommy Lee Jones , Terry Kinney , Frances McDorman , Sam Shepard , Sissy Spacek , wilford brimley , Walter Olkewicz , Matt Damon

One of Matt Damon’s least well-known movie roles came with the made-for-TV WesternThe Good Old Boys. Coming two years before Damon’s breakout success as the co-writer and star of Good Will Hunting, this star-studded TNT TV movie was also the directional debut of its lead, Tommy Lee Jones. As the story of an aging cowboy who must choose between his love for roaming free and the responsibilities of a family, Jones was joined not just by Damon but also notable stars like Frances McDormand, Sam Shepard, and Sissy Spacek.

Damon’s $20,000 paycheck gave him the freedom to focus his
Good Will Hunting
screenplay with close friend and collaborator Ben Affleck

As an adaptation of the 1978 novel of the same name by Elmer Kelton, The Good Old Boys was an enjoyable Western that has been mostly forgotten in the years since it aired. However, it featured an enjoyable supporting performance from Damon as Cotton Calloway, the son of Jones’ character Hewey. The Good Old Boys was an important moment in Damon’s career, as it not only saw him acting alongside cinematic greats, but his $20,000 paycheck (via Woman’s World) gave him the freedom to focus his Good Will Hunting screenplay with close friend and collaborator Ben Affleck.

Overall, The Good Old Boys was an enjoyable but predictable Western movie dealing with the well-worn theme of a cowboy’s conflicting desire for freedom while also wanting a family. There’s a healthy mix of comedy and drama as Damon’s charismatic skill was on full display as his role hinted toward his future as a major Hollywood star. This Western was well worth watching for those with a love for the more introspective side of the genre, but audiences with only a passing interest in slow-paced Westerns can give this one a miss.

4 Geronimo: An American Legend (1993)

Matt Damon as Britton Davis

Geronimo: An American Legend (1993) PG-13WesternDramaHistory

Geronimo: An American Legend is a historical drama directed by Walter Hill, featuring Wes Studi as Apache leader Geronimo. The film highlights the relentless pursuit of Geronimo and his followers by the U.S. Army, including officers played by Jason Patric, Matt Damon, and Robert Duvall. Set in the late 19th century, it captures the challenging and complex relationship between Native Americans and the United States government.

Director Walter Hill Release Date December 10, 1993 Writers John Milius , Larry Gross Cast Jason Patric , Gene Hackman , Robert Duvall , Wes Studi , Matt Damon , Rodney A. Grant , Kevin Tighe , Steve Reevis Character(s) Lt. Charles Gatewood , Brig. Gen. George Crook , Al Sieber , Geronimo , Lt. Britton Davis , Mangas , Brig. Gen. Nelson Miles , Chato Runtime 115 Minutes Main Genre Western Expand

Geronimo: An American Legend was one of Matt Damon’s earliest notable roles, as he played the ambitious but inexperienced cavalryman, 2nd Lieutenant Britton Davis. This account of the Apache Wars depicted how First Lieutenant Charles B. Gatewood (Jason Patric) convinced Apache leader Geronimo (Wes Studi) to surrender in 1886. While the film received mixed reviews at the time of its release, Native American groups commended Geronimo as the most honest cinematic look at the feared leader (via LA Times) and praised the casting of the Native American actor Studi in the lead role.

Geronimo
was released as the Western genre made a surprise comeback into mainstream popularity.

Produced after the success of Dances with Wolves, Geronimo was released as the Western genre made a surprise comeback into mainstream popularity. As the film walked the fine line between accurately representing the true historical narrative and showcasing Geronimo as an interesting and heroic cinematic protagonist, Geronimo was an ambitious achievement by director Walter Hill. However, this failed to register at the box office, and Geronimo bombed, taking in just $18.6 million against its $35 million budget (via Box Office Mojo.)

Damon played a supporting, albeit important role, as an associate of Lieutenant Gatewood, who, along with Robert Duvall as Chief of Scouts Al Sieber, was tasked with helping to capture Geronimo. At the heart of Geronimo was an important message about the unjust treatment of Native Americans, but the clever insights of this story were sometimes prioritized over engaging entertainment. Geronimo was a visually stunning movie with a lot to say, but unfortunately, that did not stop the movie from feeling like a bit of a drag at times.

3 All The Pretty Horses (2000)

Matt Damon as John Grady Cole

All the Pretty Horses (2000) PG-13WesternDramaRomance

All the Pretty Horses is a 2000 film directed by Billy Bob Thornton based on the Cormac McCarthy novel. Starring Matt Damon and Penélope Cruz, the story follows two young cowboys from Texas who journey to Mexico, seeking a better life working on ranches. Their adventure takes unexpected turns as they confront challenges and moral dilemmas in a foreign land.

Director Billy Bob Thornton Release Date December 25, 2000 Writers Cormac McCarthy , Ted Tally Cast Matt Damon , Penelope Cruz , Henry Thomas , Angelina Torres , J.D. Young , Laura Poe , Sam Shepard , Robert Patrick Character(s) John Grady Cole , Alejandra Villarreal , Lacey Rawlins , Luisa , Grandfather , Mother , J.C. Franklin , Cole Runtime 116 Minutes Main Genre Western Expand

As the first adaptation of a Cormac McCarthy novel, All the Pretty Horses doesn’t quite compare to superior adaptations like No Country for Old Men or The Road. Yet there was still something oddly engaging about Matt Damon’s performance as John Grady Cole, although it lacked the lean, minimalized, and declarative style that made McCarthy’s writing so incredible. With a story about Texas cowboys traveling to Mexico in search of work, Cole soon found himself in trouble with the law after he fell for a wealthy rancher’s daughter, played by Penélope Cruz.

As director Billy Bob Thorton’s followup to his excellent debut Slingblade, for which he won the Oscar for Best Actor, All the Pretty Horses had a lot to live up to and mostly succeeded in its ambition to adapt one of the great writers of modern American fiction. Damon’s performance carried much of the emotional weight of All the Pretty Horses, and rewatching the film today, it’s incredible to see the young version of his character being played by future star Jesse Plemons. As dead ringers for one another, the casting of Plemons was a stroke of genius.

All the Pretty Horses
may not live up to the lofty expectations of McCarthy purists.

An endearingly honest portrayal, Damon’s performance in All the Pretty Horses proved why his star has continually risen ever since he gained his big break with Good Will Hunting. Although All the Pretty Horses received a mixed reception upon release and failed at the box office, there was still a lot of beauty at the heart of this romance-turned-subtle-revenge story. It may not live up to the lofty expectations of McCarthy purists, but there was a lot to enjoy about this Western that followed Texans going out to find what was left of the Old West.

2 Spirit: Stallion of the Cimarron (2002)

Matt Damon as Spirit

Spirit: Stallion of the Cimarron (2002) GAnimationAdventureComedyFamilyDramaWesternRomance Where to Watch

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Spirit: Stallion of the Cimarron is an animated adventure film directed by Kelly Asbury and Lorna Cook. The story follows a wild mustang named Spirit as he navigates the challenges of taming and captivity in the American West. Matt Damon provides narration, giving voice to Spirit’s thoughts and emotions. The film combines traditional hand-drawn animation with computer-generated imagery to bring the American frontier to life.

Director Kelly Asbury , Lorna Cook Release Date May 24, 2002 Studio(s) DreamWorks Animation , DreamWorks Pictures Writers John Fusco , Michael Lucker Cast Matt Damon , James Cromwell , Charles Napier , Robert Cait , Richard McGonagle Runtime 83 Minutes Budget 80000000.0 Main Genre Animation Expand

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Spirit: Stallion Of The Cimarron was one of the greatest animated Westerns ever made and showcased Matt Damon’s skill as a voice actor, which was later exemplified in movies like Ponyo and Happy Feet Two. With Damon as the title character, Spirit was a beautiful DreamWorks movie that followed a wild Kiger mustang stallion on the American frontier. After being captured by frontiersfolk bent on taming the region, Spirit must fight for his freedom and those around him.

Like many of the best Westerns, Spirit addressed the hardships of encroaching civilization in the Wild West and how humanity’s desire for expansion impedes the delicate order of nature. With a stunning visual style, Spirit captured the majesty of horses free-roaming the 19th-century American West. While the plot may seem predictable to adult viewers, the political messaging at the heart of Spirit was easily digestible for child viewers, as the spectacular animation surely fostered a lifelong love for the beauty of horses in many young audience members.

Without goofy side characters and endless unnecessary comic relief,
Spirit
felt more pure and direct than many other kids’ animated movies of its kind.

Without goofy side characters and endless unnecessary comic relief, Spirit felt more pure and direct than many other kids’ animated movies of its kind. There’s real beauty at the heart of this story, and Spirit’s incredible traditional animation style acted as a powerful showcase of all that was lost as most children’s feature films have since switched to a primarily CGI-rendered style. As the starting point for an entire franchise, Spirit has, in recent years, received both a spin-off TV series and film on Netflix.

1 True Grit (2010)

Matt Damon as LaBoeuf

True Grit PG-13WesternDrama Where to Watch

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An adaptation of Charles Portis’ 1968 novel of the same name, True Grit tells the story of 14-year-old Mattie Ross (Hailee Steinfeld), who enlists the help of morally-questionable lawman Rooster Cogburn (Jeff Bridges) in order to avenge the death of her father by apprehending the criminal Tom Chaney (Josh Brolin). They are joined by a cocksure Texas Ranger named Labeouf (Matt Damon), who insists upon collecting the bounty on Chaney’s head. The three travel across the Arkansas plains in pursuit of Chaney, risking life and limb against outlaws and wild animals in pursuit of justice.

Director Ethan Coen , Joel Coen Release Date December 22, 2010 Studio(s) Paramount Pictures Distributor(s) Paramount Pictures Writers Joel Coen , Ethan Coen Cast Jeff Bridges , Barry Pepper , Josh Brolin , Matt Damon , Hailee Steinfeld Runtime 110 minutes Budget $38 million Main Genre Western Expand

The Coen brothers not only justified their remake of the 1969 classic John Western with the release of True Grit, but in many ways they actually outdid the original. With Jeff Bridges as Rooster Cogburn and Matt Damon as the Texas Ranger LaBoeuf, True Grit was one of the greatest Westerns of the 21st century, which was powerful, exemplified by its staggering ten Academy Award nominations. With themes of justice, vengeance, sacrifice, perseverance, and redemption, the Coen brothers once again proved that nobody could highlight the uniqueness of Americana better than them.

The real star was Hailee Steinfeld as the 14-year-old Mattie Ross, who commanded every scene she was in.

With astounding cinematography that harkened back to the glory days of the Western genre, True Grit looked incredible as it told the story of a teenager enlisting the help of the U.S. Marshall Cogburn to track down her father’s murderer. Damon’s LaBoeuf was an essential aid in this epic Wild West story, as he delivered one of the strongest performances in his entire career. However, the real star was Hailee Steinfeld as the 14-year-old Mattie Ross, who commanded every scene she was in.

True Grit was far more faithful to the original novel by Charles Portis than the Wayne version and helped elevate the story from a Western classic into a modern masterpiece. However, this did not mean that the Coen didn’t include their own signature style, as it was packed with eccentric characters and the same dark sense of humor that characterized their best work. True Grit was Matt Damon’s greatest Western, as it rose above the confines of that genre to become one of the greatest films of the 2010s.

Sources: Woman’s World, LA Times, Box Office Mojo

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