10 Greatest Portrayals Of Real Life People In Western Movies

Summary

• Real-life cowboys and outlaws in Western movies captivate audiences with their fascinating stories and talented performances by famous actors.
• Lesser-known figures also shine in Western films, uncovering hidden aspects of the Wild West and adding to the allure of the legendary period.
• Iconic performances by actors like Viggo Mortensen, Jeff Bridges, and Kris Kristofferson immortalize the memory of Wild West figures in cinematic history.

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Part of the reason the Western genre has endured for so long was its connection to the true story of America and the real people who made the Wild West such a fascinating setting. With cowboys, gunslingers, and outlaws all making their way through the American frontier, something about these folk heroes and sinister bandits connected with audiences and meant that certain real people’s stories have been adapted repeatedly. While the legends behind these real figures always made for a great story, it was also vital that they were backed up by fantastic performances by talented actors.

The greatest portrayals of real-life cowboys and outlaws in Western movies involved famous actors playing household names like Billy the Kid or Calamity Jane. However, they also included lesser-known figures whose stories were captured on screen and allowed audiences to discover hidden aspects of the Wild West and uncover the great mysteries behind the period just before America fully embraced civilization and modernity. These portrayals have kept the memory of the Wild West alive, as viewers have remained fascinated by its enigmatic allure and legendary status.

10 Viggo Mortensen As Frank Hopkins

Hidalgo (2004)

Viggo Mortensen followed his definitive portrayal of Aragorn in The Lord of the Rings with the biographical Western Hidalgo, where he played the real American distance rider, Frank Hopkins. An extraordinary tale of Hopkins’ racing his horse in Arabia in 1891 against Bedouins riding pure-blooded Arabian horses, Hidalgo was an epic adventure that failed to make much of an impression with critics. Despite this, Mortensen gave an impressive performance and highlighted a fascinating true story about a down-and-out cowboy and his famous horse.

Hidalgo underperformed at the box office, barely breaking even with a gross of $108 million against its $100 budget, although the best thing about it was Mortensen’s committed performance. The movie was scrutinized for its historical inaccuracy, as the real Frank Hopkins’s unconfirmed claims of Lakota ancestry were presented as fact. As an interesting mix of real historical stories and legends built around Hopkins and his horse, Hidalgo was an enjoyable adventure that deserved more attention.

Hidalgo
PG-13
Action
Adventure
Western
Biography

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In 1890, a down-and-out cowboy and his horse travel to Arabia to compete in a deadly cross desert horse race.

Director Joe Johnston Release Date March 5, 2004 Cast Viggo Mortensen , Zuleikha Robinson , Omar Sharif , Louise Lombard , Adam Alexi-Malle , Saïd Taghmaoui Runtime 136 minutes Main Genre Western

9 Jeff Bridges As Wild Bill Hickok

Wild Bill (1995)

Although Wild Bill totally bombed at the box office, with an abysmal gross of just $2.1 million against a $30 million budget, this did not take away from Jeff Bridges’ exceptional performance as the legendary outlaw Wild Bill Hickok. With a star-studded cast that also included John Hurt, Bruce Dern, and David Arquette, Wild Bill unfortunately suffered from a muddled plot that led to a convoluted retelling of the titular folk hero’s story. Despite this, Wild Bill succeeded as a character study driven by Bridges’ committed performance and strong suitability for the role.

The real Wild Bill was a folk hero of the American Old West who gained incredible notoriety for participating in many famous gunfights. Wild Bill has been portrayed countless times across various media, starting with the silent era picture Wild Bill Hickok from 1923, right up to more recent films such as the Coen brothers’ The Ballad of Buster Scruggs. While Wild Bill may not have gone down in history as among the best Westerns ever, it must be admitted that Bridges’ portrayal stood out as a real highlight.

Wild Bill (1995)
R
Action
Biography
Drama

The early career of legendary lawman Wild Bill Hickock is telescoped and culminates in his relocation in Deadwood and a reunion with Calamity Jane.

Director Walter Hill Release Date December 1, 1995 Cast Jeff Bridges , Ellen Barkin , John Hurt , Diane Lane , Keith Carradine , David Arquette , Christina Applegate , Bruce Dern Main Genre Drama Writers Peter Dexter , Thomas Babe , Walter Hill

8 Kris Kristofferson As Billy the Kid

Pat Garrett and Billy the Kid (1973)

As a legendary country singer in his own right, Kris Kristofferson already had plenty of Western credentials when he starred alongside James Coburn in Sam Peckinpah’s revisionist Western Pat Garrett and Billy the Kid. In his role, Kristofferson delivered one of the best portrayals of Billy the Kid, and although the film received mixed reviews upon release, it has since been reappraised as a classic Western of the 1970s. With an iconic soundtrack by Bob Dylan, Pat Garrett and Billy the Kid was known for using the song “Knockin’ on Heaven’s Door,” where Dylan’s lyrics directly commented on a scene in the film.

In his portrayal, Kristofferson captured the legendary aura that has propagated the story of Billy the Kid over the years. As an outlaw and a gunman who was said to have killed 21 men before he turned 21, Kristofferson’s brooding presence and formidable stature stood in stark contrast to the real Billy’s lanky, less imposing presence. Pat Garrett and Billy the Kid helped showcase the respect that Billy earned among outlaws in the Wild West and why his name became entrenched as one of the most recognizable gunfighters who ever lived.

Pat Garrett And Billy The Kid
R
Western

Pat Garrett, a sheriff determined to bring order to the West, is pitted against his former friend, the infamous Billy the Kid. As Garrett hunts him, they both grapple with memories of their past camaraderie and the choices that have set them on opposing paths.

Director Sam Peckinpah Release Date May 23, 1973 Cast James Coburn , Kris Kristofferson , bob dylan , Jason Robards , Katy Jurado , Chill Wills Runtime 122 Minutes Studio(s) Metro-Goldwyn-Mayer Distributor(s) Metro-Goldwyn-Mayer Writers Rudy Wurlitzer Budget $4.64 Million

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7 Doris Day As Calamity Jane

Calamity Jane (1953)

While many cinematic portrayals of the Wild West heroine Calamity Jane delved into the darkest aspects of her story, this was not the case for the upbeat Western musical Calamity Jane with Doris Day. Loosely based on the real legend, Calamity Jane explored the alleged romance between Jane and Wild Bill Hickok in 1870s South Dakokda. With LGBTQ+ undertones related to Jane’s life as a strong, independent woman sharing a home with another woman (via Stuart), Calamity Jane may look frivolous on the outset but was full of hidden subtext.

Although Calamity Jane portrayed its star and Hickok as lovers, historians have found no proof of this beyond their established acquaintance. Jane was a known teller of tales, and this was hilariously explored in Calamity Jane as she played fast-and-loose with the truth when telling other cowboys about her dangerous exploits. Despite potential historical inaccuracies, Day gave a fun performance as Jane and made this a must-watch for lovers of old-style Western musicals.

Calamity Jane (1953)
Approved
Western
Musical
Romance

The story of Calamity Jane, her saloon, and her romance with Wild Bill Hickok.

Director David Butler Release Date November 4, 1953 Cast Doris Day , Howard Keel , Allyn Ann McLerie , Philip Carey , Dick Wesson , Paul Harvey , Chubby Johnson , Gale Robbins Main Genre Western Writers James O’Hanlon

6 Ian McShane As Al Swearengen

Deadwood: The Movie (2019)

Ian McShane delivered one of the most iconic Western performances of all time in the HBO drama series Deadwood, a fantastic show that explored the crumbling of the Wild West as modernity and civilization started to take hold. As the foul-mouthed owner of the Gem Saloon, Al Swearengen was an all-time great television character who found his way into the world of feature films with the long-anticipated release of Deadwood: The Movie in 2019. This epilogue to the series was set ten years after its conclusion and allowed for a proper finale to the Western drama that was canceled too soon.

McShane imbued Swearengen with character. As the most pivotal resident of the town of Deadwood, he made careful calculations to ensure his needs were always met, even if they came at the expense of others. The real Swearengen was also said to be a brutal and infamous man (via Deadwood) who lured desperate women into working for him and becoming prostitutes. After leaving Deadwood when the Gem Saloon burned to the ground, Swearengen was found dead by a streetcar in Denver, and authorities never determined if there was foul play or not.

Deadwood: The Movie
r
Western
Action

A continuation of the HBO series of the same name, Deadwood reunites the acclaimed series’ ensemble cast. As South Dakota celebrates its statehood, the residents of Deadwood still have grudges to satisfy and scores to settle.

Director Daniel Minahan Release Date May 31, 2019 Studio(s) Warner Bros. Pictures Distributor(s) Warner Bros. Pictures Writers David Milch Cast Timothy Olyphant , Ian McShane , Molly Parker , Paula Malcomson , W. Earl Brown , Dayton Callie , Kim Dickens , Brad Dourif , Anna Gunn , John Hawkes , Leon Rippy , William Sanderson , Robin Weigert , Brent Sexton , Sean Bridgers , Gerald McRaney , Keone Young Runtime 110 minutes prequel(s) Deadwood: The Movie Budget $20.7 million

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5 Lily Gladstone As Mollie Burkhart

Killers of the Flower Moon (2023)

Rather than highlighting the exploits of outlaws and cowboys, Martin Scorsese’s epic Western Killers of the Flower Moon addressed the exploitation of the Osage Nation as white Americans sought to steal tribal wealth. In a movie full of extraordinary performances by Leonardo DiCaprio and Robert De Niro, Lily Gladstone’s portrayal of Mollie Burkhart stood out among the rest. As a stern and determined woman, it was heartbreaking to witness Mollie slowly growing weaker as her husband Ernest (DiCaprio) poisoned her insulin in order to slow her down.

The real Mollie Burkhart thankfully survived the hidden agenda of the corrupt political boss William King Hale (De Niro) as she divorced Ernest and was able to rejoin control of her family and guardianship. Killers of the Flower Moon highlighted a dark part of America’s history, and Gladstone effectively captured the struggles faced by indigenous peoples. As a truly spellbinding performance, Gladstone was deservedly nominated for an Academy Award for Best Actress for her role as Mollie.

Killers of the Flower Moon
History
Drama
Crime

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Killers of the Flower Moon is the next film from director Martin Scorsese, based on the non-fiction book Killers of the Flower Moon: The Osage Murders and the Birth of the FBI, initially captured by David Grann. When members of the Osage tribe are murdered in the 1920s via mysterious circumstances shortly after the discovery of oil on Native-American soil, the FBI is established to uncover the true reason behind them.

Director Martin Scorsese Studio(s) Paramount Pictures Distributor(s) Apple , Paramount Pictures Writers Eric Roth , Martin Scorsese Cast Leonardo DiCaprio , Louis Cancelmi , Jillian Dion , Scott Shepherd , Jesse Plemons , JaNae Collins , Robert De Niro , Jason Isbell , Cara Jade Myers , Lily Gladstone Runtime 200minutes Budget $200 million

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4 Paul Newman As Butch Cassidy

Butch Cassidy and the Sundance Kid (1969)

Paul Newman truly encapsulated his effortlessly cool persona with the role of Butch Cassidy in the iconic buddy Western Butch Cassidy and the Sundance Kid. As one of Newman’s definitive roles, the character of Butch Cassidy was made all the more impactful due to his incredible onscreen chemistry with Robert Redford as the Sundance Kid. Although Butch Cassidy was based on a real man, Newman truly made the role his own and cemented the ‘Wild Bunch’ outlaw’s place in cinematic history.

The real Butch Cassidy was a train robber, a bank thief, and a member of the notorious Wild Bunch gang of the Old West. With a life that’s been dramatized countless times across film and television, Newman brought some of his unique cinematic charms to the role and ensured Butch Cassidy and the Sundance Kid a place among the greatest Western classics. As an essential film for the New Hollywood era, Newman’s portrayal would influence every subsequent generation of actors hoping to mimic his innate charm.

Butch Cassidy and the Sundance Kid
pg-13
Western
Drama

Butch Cassidy & The Sundance Kid is a classic Western film that follows the titular characters, who conduct robberies and face off against the law. The story highlights their close friendship and exploits in the wild west and beyond, with their eventual revitalized outlaw life in a new country, Bolivia.

Director Mark Tonderai Release Date September 23, 1969 Studio(s) 20th Century Distributor(s) 20th Century Writers Mark Tonderai Cast Robert Redford Runtime 110 minutes

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3 Kurt Russell As Wyatt Earp

Tombstone (1993)

The true story of the Gunfight at the O.K. Corral and the friendship between Wyatt Earp and Doc Holliday has been continually adapted throughout the years, but Tombstone with Kurt Russell as Wyatt Earp stood as the definitive retelling of this legend. As a film that acted as a loose retelling of the true stories of several outlaws, Russell brought a modern attitude and energy to a story Western lovers will already be more than familiar with. With an impressive mustache and a striking black cowboy hat, even the iconography of Russell as Wyatt Earp in Tombstone was powerfully memorable.

The real Earp was famous for his involvement in the Gunfight at the O.K. Corral and was a key figure in the notable shootout that saw lawmen kill three outlaw Cochise County Cowboys. As a lawman and gambler, Earp was significant for his ability to traverse both sides of the law and his friendship with the notorious Doc Holliday. Tombstone was a film full of incredible performances, and Russell stood out as among the most enjoyable aspects of the woefully underappreciated movie.

Tombstone
R
Western
Drama
History
Action
Biography

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Tombstone is a Western film loosely based on true events in the 1880s and features an ensemble cast including Kurt Russell, Val Kilmer, and Sam Elliot. When a group of outlaws known as the Cowboys ride into a town and slay several police officers for revenge for the death of two of their gang members, word of their misdeeds reaches the ears of a retired lawman. Gathering a group together, the new vigilantes will defend the town and aim to end the terror of the Cowboys.

Director George P. Cosmatos Release Date December 25, 1993 Studio(s) Disney Distributor(s) Disney Writers Kevin Jarre Cast Bill Paxton , Charlton Heston , Sam Elliott , Powers Boothe , Val Kilmer , Kurt Russell , Michael Biehn , Jason Priestley Runtime 130 minutes Budget $25 million

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2 Leonardo DiCaprio As Hugh Glass

The Revenant (2015)

After five previous nominations, Leonardo DiCaprio finally took home the Academy Award for Best Actor for his portrayal of Hugh Glass in The Revenant. In a grueling and committed performance, DiCaprio gave his all to the epic Western story about a man exploring the uncharted wilderness and fighting to survive after being mauled by a bear and left for dead. An extraordinary achievement by director Alejandro G. Iñárritu, DiCaprio utilized a method acting style as he slept inside an animal carcass and ate the raw liver of a bison for the role.

DiCaprio’s intense commitment to realism for The Revenant was even more impressive, considering his veganism. While the truth behind The Revenant and Glass’s interaction with grizzly bears has been undisputed, the realism of DiCaprio’s performance made it feel like audiences were right there with Glass as he crawled and stumbled 200 miles to safety. As an extraordinarily absorbing tale, DiCaprio put his all into The Revenant.

The Revenant
R
Adventure
Drama

Inspired by the true events in the life of Hugh Glass, The Revenant is an action-drama movie that sees Leonardo DiCaprio in the starring role. Betrayed and left for dead by one of the members of his hunting group, Glass finds himself contending with some of the harshest elements imaginable while tending to his deadly wounds, as his will to carry on and need for revenge push him to carry on in this gripping tale of survival.

Director Alejandro González Iñárritu Release Date December 25, 2015 Studio(s) 20th Century Distributor(s) 20th Century Writers Alejandro González Iñárritu , Mark L. Smith Cast will poulter , Leonardo DiCaprio , Paul Anderson , Tom Hardy , Domhnall Gleeson Runtime 156minutes Budget $135 million

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Is The Revenant Based On A True Story?

The Oscar-winning The Revenant features graphic displays of survival, which has led many to questions whether its events are rooted in the truth.

1 Val Kilmer As Doc Holliday

Tombstone (1993)

While Kurt Russell truly impressed as Wyatt Earp in Tombstone, it must be admitted that Val Kilmer stole the show with his exceptional portrayal of Doc Holliday. As the best portrayal of Doc Holliday on screen, Kilmer perfectly captured the hard-drinking dentist outlaw and stole every scene he was in. Although Tombstone did not get the love it deserved when it was first released, it has since gained a reputation as a cult classic, and Kilmer’s performance has received universal acclaim.

Doc Holliday has been consistently portrayed over the years, from Harvey Clark in Law for Tombstone in 1937 right up to modern television series like Tim Rozon in Wynonna Earp. However, it was Kilmer who truly captured the essence of the real man and will be forever remembered as the definitive portrayal of Doc Holliday. A Western anti-hero whose popularity has continued to grow, Doc Holliday was a fascinating and enduring figure of the Wild West.

Sources: All box office figures from Box Office Mojo, Performing Queer Female Identity on Screen by Jamie Stuart, Deadwood

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