All 36 Will Rogers Movies (in Order)

Published: 2025-05-24T10:55:10.323Z

Discover the classic charm and wit of Will Rogers in our movie roundup. From heartwarming westerns to amusing comedies, we have compiled a list of memorable films featuring this beloved American personality. Get ready to reminisce and enjoy some timeless cinematic experiences.

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1. The Headless Horseman (1922)

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Get ready for a spine-tingling adventure with the classic tale of "The Headless Horseman. " Set in the early 1920s, this movie takes us to the picturesque village of Sleepy Hollow, where a new schoolteacher, Ichabod Crane, arrives from the bustling city of New York. Crane soon hears about the village's chilling legend - the headless horseman who lost his head in battle and is now searching for it.



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2. Hollywood (1923)

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Hollywood (1923) is a charming film set in the glamorous surroundings of Tinseltown. The plot revolves around Angela, a young woman who has come to Hollywood with two dreams: to become a movie star and to bring her ailing grandfather back to Centerville. However, life in the movie capital proves to be more challenging than she anticipated. With countless stars gracing her presence and countless casting offices to knock on, Angela is yet to secure her dream job by the end of her first day.



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3. A Texas Steer (1927)

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A Texas Steer" is a delightful silent comedy from 1927 starring the legendary Will Rogers. Maverick Brander, a laconic cowboy, is unknowingly a wealthy rancher. However, his wife and daughter, as well as his political ambitions, lead him into plenty of trouble. Aided by her social climbing aspirations and political bosses, Maverick's wife connives to launch him into Congress, a choice that leads to comedic mayhem.



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4. Happy Days (1929)

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In the 1929 silent film "Happy Days, " beloved actress Margie leaves her showboat behind to pursue her dreams in the city that never sleeps - New York City. However, she remains in love with the owner's grandson. As the showboat's financial troubles mount, Margie musters all of the former stars to join forces in a grand show to save it.



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5. Ambassador Bill (1931)

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Ambassador Bill, " released in 1931, is a lighthearted comedy film that takes place in a politically-charged small country. The story revolves around the arrival of an American ambassador who is tasked with befriending the young boy destined to become the nation's king. The ambassador's role is to ensure the boy is prepared for the throne and to guarantee his protection from the tumultuous political climate and civil unrest plaguing the country.



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6. A Connecticut Yankee (1931)

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A Connecticut Yankee" is a whimsical comedy-fantasy film that transports its viewers to the mystical realm of King Arthur's Court. Hank Morgan, a man from modern times, inexplicably finds himself transported back to the medieval era after being knocked unconscious. As he navigates this new world, Morgan experiences a series of enchanting and humorous encounters with the legendary knights and their enchanting queen, Guinevere.



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7. Business and Pleasure (1932)

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Embark on a thrilling Mediterranean adventure with Business and Pleasure (1932), a lighthearted comedy. The film stars acclaimed actor Will Rogers as Earl Tinker, a razor blade manufacturer who embarks on a luxurious cruise.



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8. Down to Earth (1932)

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Down to Earth" is a lighthearted comedy from 1932 that explores the shifting dynamics of wealth when the Great Depression hits. The film follows the Pike Peters family as they navigate their newfound financial struggles and the consequences that come with them. Filled with charming humor and witty one-liners, this movie takes a humorous look at the challenges of balancing family relationships during difficult times.



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9. Doctor Bull (1933)

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Doctor Bull, " a 1933 comedy-drama, features the strong-willed country doctor Doc Bull, played by the charming and talented Will Rogers. This wise doctor has spent decades serving his tight-knit, yet prejudiced community. Despite these challenges and the small-town provincialism, Doc Bull refuses to give in to the injustice that plagues his town.



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10. Judge Priest (1934)

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In the post-Civil War era of 1868 Kentucky, Judge Priest (Will Rogers) takes justice into his own hands, using his combination of common sense and empathy to maintain order in his small town. A devoted Confederate veteran, Judge Priest navigates the challenges of Post-Bellum life with a wit and warmth that resonate strongly with the community. Despite the setting, the film's themes of justice, compassion, and human understanding ring true, offering an enduring message that transcends the era.



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11. Handy Andy (1934)

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Handy Andy" is a delightful 1934 comedy film set in a quaint small town. The titular character, a sweet yet hapless druggist, is constantly on the receiving end of his demanding wife's scheming. She pressures him to sell their family pharmacy to a powerful, national pharmacy chain. In addition, she attempts to arrange a match between her charming young daughter and the clueless heir of the chain's owner. However, her daughter secretly harbors affection for the dashing son of the town doctor, which leads to a hilarious mix-up.



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12. The County Chairman (1935)

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The County Chairman (1935) is a heartwarming and humorous tale that takes audiences on a journey through the political landscape of a Wyoming county. Set against the backdrop of an election where women's rights to vote takes center stage, the film explores the choices and dilemmas of a local party-boss named Jim Hackler.



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13. Steamboat Round the Bend (1935)

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In the heart of Louisiana's 1890s, fast-talking con man Jim Brackett (Will Rogers) plans to win a high-stakes race with rival Sam Boone (Irvin S. Cobb) on his steamboat, the "Raven. " Tensions are high as they compete, but Jim has a secret agenda: he's trying to find the witness who will clear his nephew's name, who's about to face the hangman's noose for a murder he didn't commit.



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14. The Golden Age of Comedy (1957)

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Get ready for a hilarious journey into the golden era of comedy with 'The Golden Age of Comedy'! . This delightful compilation features some of the best-known comedians from the silent era, showcasing their incredible talent and charm in their most iconic films. With a runtime of just 1 hour and 19 minutes, this movie is the perfect way to enjoy some timeless slapstick and sketch comedy.



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15. The Legend of Rudolph Valentino (1961)

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The Legend of Rudolph Valentino" is a 1961 documentary that delves into the life and legacy of Hollywood's first Latin heartthrob. Exploring the complexities of his personal life and the paradoxes of his persona, the film also provides an insight into the societal pressures faced by celebrity immigrants in the early 20th century. Valentino, a charismatic actor adored for his portrayal of Latin lovers, faced an untimely demise that is also covered in the piece.



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16. Brother Can You Spare a Dime (1975)

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In "Brother Can You Spare a Dime, " director Philippe Mora takes us on a nostalgic journey through the turbulent times of the Great Depression. Using contemporary archival footage and film clips, the documentary follows the life of James Cagney as an American Everyman, navigating the hardships and challenges faced by many during that era.



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17. Bob Hope's World of Comedy (1976)

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In 1976, American comedy legend Bob Hope joined forces with renowned creative minds to bring the "Bob Hope's World of Comedy" tv special to life. This two-hour, comedic masterpiece features a lineup of hilarious sketches and entertaining music performances that showcase the timeless talent of Bob Hope and his illustrious co-stars. Don't miss the opportunity to witness this classic TV special as it delivers the laughter and charm that only Bob Hope can provide.



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18. Going Hollywood: The '30s (1984)

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Going Hollywood: The '30s" is a gripping 1984 documentary that dives into the fascinating world of Hollywood during the 1930s, a time of both glitz and grit. Set against the backdrop of the Great Depression, this film explores how the industry adapted and thrived amidst economic uncertainty. The documentary features exclusive interviews with notable personalities from that era, including George Arliss and Gracie Allen, providing a unique insight into the lives and careers of the stars who graced the silver screen.



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19. John Ford (1992)

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Delve into the fascinating world of film history and western filmmaking with "John Ford" (1992), a captivating biography documentary that explores the life and work of legendary director John Ford. This enlightening film takes viewers on a journey through Ford's illustrious career, from his iconic gun battles and thrilling street shootouts, to his highly praised "Gunfight at the O. K. Corral. " With in-depth interviews and exclusive footage, "John Ford" is a must-see for cinephiles and history buffs alike.



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20. Legends of Comedy (1992)

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Embark on a hilarious journey through the archives of comedy in "Legends of Comedy" (1992), a captivating 2-hour and 45-minute documentary. Showcasing over 50 legends from vaudeville to video, this film takes you on a spellbinding journey through the world of comedy. From the Great White Way to the silver screen, each comedic master is given their own mesmerizing segment, allowing you to witness their finest performances and most legendary moments.



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21. Mo' Funny: Black Comedy in America (1993)

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Mo' Funny: Black Comedy in America" is a thought-provoking documentary that explores the rich cultural history of African American humor. As early as the minstrel shows in the early 1900s, to the iconic performances of the 1980s and 1990s, this film unravels the fascinating journey of black comedy through the decades. Yvonne Smith's masterful directing and insightful commentary make this documentary a must-watch for fans of dark comedy, African American culture, and history.



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22. Twentieth Century Fox: The First 50 Years (1997)

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Twentieth Century Fox: The First 50 Years takes viewers on a captivating journey through the history of one of the world's most renowned film studios. Starting with the studio's beginnings under the visionary Hungarian immigrant, William Fox, the documentary delves into the evolution of the company as it transformed from a small film distribution business to a major Hollywood player.



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23. Certainty (2011)

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Certainty" is a drama that follows the love story of Deb and Dom, a lively, young couple on the cusp of marrying. As they seek guidance from the Catholic Church, the couple encounters some unexpected challenges in their relationship and with their friends. This film paints a compelling and realistic picture of life's hardships, revealing the impact that religion can have on the future of a couple.



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24. Happy New Year (2011)

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Happy New Year" is a gripping drama that explores the aftermath of war on one soldier's soul. Set in the context of both the Afghanistan and Iraq wars, this intense movie follows the story of a young Marine, returning home from combat, only to face an even more challenging fight - the battle within himself. As he grapples with the devastating effects of Post Traumatic Stress Disorder (PTSD), the film delves into the unspoken traumas faced by many soldiers, illustrating how war can reverberate long after the battles have ended.



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25. The Bay (2012)

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The Bay" is an intense and suspenseful movie that takes place in a small town in Maryland, after a catastrophic event involving environmental contamination in the water. The film was released in 2012 under the direction of Barry Levinson and features a talented cast, including Will Rogers and Kristen Connolly. It is a horror, science-fiction, and thriller film, highlighting the severity of ecological disasters and their potential consequences.



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26. Nancy, Please (2012)

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Nancy, Please is a dark comedy that follows the twisted tale of revenge. When a young woman named Nancy enrolls in university, she finds herself seeking a new roommate to help ease her transition to campus life. Nancy's quest leads her to select a seemingly harmless individual, but the situation quickly spirals out of control when the new roommate takes things too far.



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27. A Good Marriage (2014)

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A Good Marriage, released in 2014, explores the dark and twisted depths of a seemingly perfect marriage. Darcy and Bob have been together for 25 years, sharing love and laughter. But when Darcy stumbles upon a chilling secret about her husband, their world is shattered, and she is forced to confront a sinister reality.



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28. Bridge of Spies (2015)

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During the tense Cold War era, an American lawyer must risk everything to defend a captured Soviet spy in court. After successfully securing the spy's release, he's called upon to facilitate a high-stakes exchange, swapping the Soviet spy with an American U2 spy plane pilot, Francis Gary Powers, who was captured by the Soviet Union. Set against the backdrop of the Berlin Wall, Steven Spielberg delivers an thrilling, drama-packed tale of espionage, betrayal, and courage with an all-star cast, including Tom Hanks, Mark Rylance, and Alan Alda.



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29. The Creek When He Came Back (2016)

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The Creek When He Came Back, released in 2016, is a captivating drama that follows the story of a woman named Chris, who finds herself lost in her life and relationship. On the verge of giving up, Chris leaves a party and encounters a young photographer who takes her to his family's country home in upstate New York. The house, situated near a mysterious creek, becomes a haven for new beginnings and healing.



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30. Rebel in the Rye (2017)

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Rebel in the Rye" is the captivating and intriguing biographical drama that delves into the life of the world-renowned, yet reclusive author, J. D. Salinger.



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31. A Bad Idea Gone Wrong (2017)

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A Bad Idea Gone Wrong" is a hilarious 2017 comedy movie directed by Jason Headley and starring Matt Jones, Will Rogers, and Eleanore Pienta. The plot revolves around two would-be thieves who make a mistake that leads to an unexpected situation - they accidentally trap themselves in a house they were planning to rob.



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32. Hearts Beat Loud (2018)

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In the heartwarming and musical comedy-drama "Hearts Beat Loud, " gifted high school student Samantha (Kiersey Clemons) and her beloved father Frank (Nick Offerman) form an improbable songwriting team as they prepare for college. In a summer brimming with love, laughter, and luminous melodies, their bond deepens while they create music that transcends generations. The film, directed by Brett Haley and written by Haley and Marc Basch, weaves a tale of resilience, familial connections, and the universal language of song.



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33. Before Someone Gets Hurt (2018)

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Before Someone Gets Hurt, a thrilling 2018 horror movie, follows the exploits of Tim and his team of ghost hunters. Known for their penchant for pranks, they quickly find themselves at the center of an actual haunting.



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34. All You Can Eat (2018)

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Prepare yourself for a side-splitting journey with "All You Can Eat, " a heartwarming comedy that tackles a heavy subject with ease. Follow the story of Danny, a larger-than-life character who loves food more than anything else. But when he discovers a new love interest, he gets caught in a hilarious dilemma that forces him to face his weight issues head-on.



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35. A Rainy Day in New York (2019)

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A Rainy Day in New York (2019) is a charming, heartwarming comedy-romance film that follows a young couple as they navigate a weekend in the city. Timothée Chalamet and Elle Fanning brilliantly portray the couple, dealing with the challenges of love, infidelity, and their complicated relationship against the backdrop of New York City's iconic landmarks. The film's beautiful, whimsical narrative is helmed by renowned director Woody Allen and masterfully written by himself.



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36. Adopting Audrey (2021)

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Adopting Audrey, " also known as "Porcupine, " is a heartfelt drama film released in 2021. The movie centers around an adult woman, played by Jena Malone, who decides to put herself up for adoption. As fate would have it, she finds herself in the hands of a family led by a grumpy patriarch, portrayed by Robert Hunger-Bühler.



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