All 28 Frank Sinatra Movies In Order — All The Best (And Worst) Films To Watch Online

Tara Schultz
9 min readJun 13, 2024

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Delve into the world of Frank Sinatra, the iconic crooner, with a roundup of his most memorable movies. From his dramatic roles in Hollywood classics to his charming performances in romantic dramas, this article takes you on a journey through Sinatra’s illustrious filmography.

Get ready to discover the versatility of Frank Sinatra as you explore his film legacy with this comprehensive roundup of his most notable movies. Whether you’re a fan of his music or simply intrigued by his acting talent, join us as we explore the silver screen through the eyes of the legendary Frank Sinatra.

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1. I Love Liberty (1982)

Get ready for a patriotic extravaganza as I Love Liberty (1982) brings together some of the biggest names in entertainment for an unforgettable all-star variety special celebrating America. Filled with music, laughter, and heartwarming moments, this TV special boasts an incredible lineup of stars, including The Muppets, who showcase their unique blend of humor and talent. I Love Liberty offers the perfect balance of nostalgia, American pride, and infectious joy, earning it 3 Primetime Emmy nominations and 1 win.

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2. Cannonball Run II (1984)

“Cannonball Run II” is a thrilling action-comedy that brings back the original characters from the 1981 hit “The Cannonball Run. “ The film, released in 1984, follows the group as they race across the country once more, this time in an array of cars and trucks. Loaded with heart-pounding car action scenes and plenty of laughs, the movie has become a fan favorite with its high-speed chase sequences and endearing cast.

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3. Holiday Greetings from ‘The Ed Sullivan Show’ (1992)

Step back in time with “Holiday Greetings from ‘The Ed Sullivan Show’”. This delightful 1992 television special takes you on a nostalgic journey through the iconic show’s history.

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4. Mrs. Doubtfire (1993)

After a tumultuous divorce, an actor must disguise himself as a female housekeeper in order to spend time with his children who are held in custody by his former wife. Robin Williams stars as the lovable yet unconventional Daniel Hillard, an unemployed voice actor unable to hold down a steady job and a devoted father to his three children.

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5. This Boy’s Life (1993)

“This Boy’s Life, “ a gripping 1993 biographical drama directed by Michael Caton-Jones, unfolds an unsettling narrative based on the memoirs of writer Tobias Wolff. The film transports viewers to a dysfunctional 1950s household where rebellion and abuse converge.

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6. The First 100 Years: A Celebration of American Movies (1995)

“The First 100 Years: A Celebration of American Movies” takes us on a captivating journey through the history of Hollywood, the world’s largest exporter of films, as it marks its centenary in 1995. The documentary, directed by Charlie Workman, explores the lives and careers of actors, writers, and other influential figures who helped shape the movie industry.

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7. The Celluloid Closet (1995)

“The Celluloid Closet” is a groundbreaking documentary that delves into Hollywood’s portrayal of homosexuality and the attitudes behind these depictions. Beginning in the early days of cinema and continuing through North American film history, the movie offers an in-depth exploration of the evolution of gay and lesbian characters on-screen. This fascinating journey sheds light on both the progression of these portrayals and the underlying homophobia that has influenced them.

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8. The Devil’s Advocate (1997)

In The Devil’s Advocate, a gifted Florida lawyer receives an offer of a lifetime: a lucrative position at a prestigious New York City law firm headed by an enigmatic and powerful boss. As he grapples with the new opportunity, the lawyer soon discovers a supernatural mystery that shakes his beliefs and tests his moral compass. A gripping fantasy drama with a dark and suspenseful twist, the movie stars Keanu Reeves, Al Pacino, and Charlize Theron, and features captivating themes of power, redemption, and the battle between good and evil.

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9. Saturday Night Live: The Best of Phil Hartman (1998)

Delve into a world of comedy and social satire with “Saturday Night Live: The Best of Phil Hartman, “ a gripping DVD featuring the best moments of Phil Hartman’s incredible career as a beloved cast member of the iconic late-night sketch comedy show. This unforgettable retrospective showcases the undeniable talent of Hartman, who brought countless memorable characters to life with his remarkable ability to embody each one in a truly unique way.

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10. The Corruptor (1999)

When a dedicated immigrant cop, Ah Jong (Chow Yun-Fat), teams up with a young, idealistic New York City detective, Danny (Mark Wahlberg), their mission to dismantle the drug-trafficking and corruption within the Chinese Triads takes a dangerous turn. As Ah Jong and Danny uncover a massive conspiracy, things become even more perilous when the Triads begin a desperate effort to bribe Danny.

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11. Catch Me If You Can (2002)

In the gripping 2002 drama “Catch Me If You Can, “ directed by Steven Spielberg, a young and talented forger named Frank takes on multiple personas as he effortlessly passes off as a doctor, lawyer, and pilot. As he revels in his deceptions and masterfully eludes capture, the relentless FBI agent Carl becomes increasingly fixated on tracking down the elusive con man.

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12. The Kid Stays in the Picture (2002)

“The Kid Stays in the Picture” is a captivating documentary that delves into the life of legendary film producer Robert Evans. Evans, the mind behind influential movies like “Chinatown, “ “Harold and Maude, “ and “Coma, “ takes the audience on a thrilling journey through his life, his triumphs, his follies, and everything that lies in between. The movie is named after Evans’s famous 1994 autobiography, which shares the same title as the film itself.

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13. Mayor of the Sunset Strip (2003)

“Mayor of the Sunset Strip” is a fascinating 2003 documentary film directed by the late George Hickenlooper. The film provides an intriguing look at the world of fame through the eyes of renowned pop star impresario, Rodney Bingenheimer. The documentary delves into Bingenheimer’s personal and professional life, unveiling the highs and lows of his quest for stardom. Featuring references to prominent figures in the music industry such as Andy Warhol, Blondie, and the Sex Pistols, the film offers a unique perspective on the music scene of the late 1970s and early 1980s.

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14. The Polar Express (2004)

Embark on a heartwarming journey through the snowy wilderness with “The Polar Express” (2004). Directed by the imaginative Robert Zemeckis, this enchanting adaptation of the beloved book by Chris Van Allsburg brings the story to life like never before.

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15. Click (2006)

“Click” is a hilarious, heartwarming, and utterly engaging comedy-drama directed by Frank Coraci. Adam Sandler stars as Michael Newman, an obsessive workaholic architect, who stumbles upon a magical universal remote that grants him the ability to fast-forward and rewind through his life. This seemingly perfect solution to his chaotic existence soon turns into a web of complications.

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16. Mr. Warmth: The Don Rickles Project (2007)

Mr. Warmth: The Don Rickles Project is a captivating documentary that delves into the extraordinary life and career of Don Rickles, one of the most influential comedians of all time. Hailed as a “classic” by modern comics, this film explores the personal stories and chance encounters that shaped Don Rickles’ journey to stardom.

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17. The 50th Annual Grammy Awards (2008)

The 50th Annual Grammy Awards takes the audience on a journey to celebrate the unforgettable milestone with an extravagant evening filled with tributes to the legends, heartwarming performances by the industry’s brightest stars, and the highly anticipated announcement of the year’s awards. The music’s magic unfolds through live broadcasts, taking the viewers on a musical rollercoaster of emotions, laughter, and sheer brilliance. With prestigious awards on the line, this television special holds a special place, having won 3 Primetime Emmys out of 3 wins and 2 nomations total, reflecting its status as a standout music event.

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18. The 80th Annual Academy Awards (2008)

The 80th Annual Academy Awards, known as the Oscars, is a prestigious event that celebrates the achievements in the motion picture industry. This specific ceremony, hosted by Jon Stewart, honors the outstanding films released in 2007.

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19. That’s My Boy (2012)

That’s My Boy, directed by Sean Anders and starring Adam Sandler, Andy Samberg, and Leighton Meester, is a 2012 comedy that takes the audience on a rollercoaster of emotions. The story centers around Donny Berger, played by Sandler, a manchild who faces a significant challenge when he returns to his estranged son Todd’s life, just as the latter is preparing to get married. The return triggers chaos and hilarious encounters as Todd’s world spirals out of control.

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20. The 2012 Comedy Awards (2012)

Prepare to laugh your socks off as you dive into the witty world of “The 2012 Comedy Awards. “ This hilarious 2012 television special brings together the biggest names in comedy, all vying for the coveted award. With a star-studded lineup, including Will Arnett, Louis C. K. , and Jim Carrey, this event promises to be an unforgettable night of comedy and entertainment. The 2012 Comedy Awards marks a significant moment in television history, showcasing the best of the decade in comedy.

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21. Silver Linings Playbook (2012)

Silver Linings Playbook (2012) is a heartwarming and humorous film about love, mental health, and the triumph of hope. The film narrates the story of Pat Solitano, a bipolar man who returns to live with his parents after a stay at a mental institution. He is working towards reconciling with his ex-wife, Nikki despite her infidelity. Pat’s life takes a turn when he meets Tiffany, a young widow dealing with her own unresolved issues.

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22. American Hustle (2013)

“American Hustle” is set in 1970s New Jersey and revolves around three central characters: the cunning Irving Rosenfeld (Christian Bale), his irresistible partner Sydney Prosser (Amy Adams), and the unpredictable F. B. I. Agent Richie DiMaso (Bradley Cooper). The story takes an unexpected twist when these two con artists from the world of hustlers find themselves unwillingly thrust into a dangerous game with corrupt power brokers and Mafia syndicates, all at DiMaso’s provocation.

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23. And the Oscar Goes to… (2014)

“And the Oscar Goes to. . “ is a documentary that takes a captivating journey through the fascinating history of the prestigious Academy Awards. The film unravels the stories behind the iconic statuette, offering an insightful look at the people, milestones, and drama that shaped the Oscars.

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24. Joy (2015)

Joy, a captivating 2015 film directed by David O. Russell, follows the incredible rise of its titular character, played by the incomparable Jennifer Lawrence.

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25. Blade Runner 2049 (2017)

In the much-anticipated sequel, Blade Runner 2049, we follow the journey of young Blade Runner K, who uncovers a shocking secret that leads him on a thrilling quest to locate the long-missing former Blade Runner, Rick Deckard, who has been absent for thirty years. This sequel, set 30 years after the original film, delves into a chilling dystopian future, where humanity is on the edge due to severe environmental damage. The movie tackles the profound themes of memory, implantation, and the essence of what it means to be human, as K navigates the perils of his mission and unravels hidden links to Wallace, the CEO responsible for the manufacture of replicants.

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26. The Oscars (2017)

“Experience the glamour, drama, and surprises of the 2017 Oscars ceremony, hosted by Jimmy Kimmel and featuring an incredible lineup of stars. Join the global celebration of cinema as the prestigious 89th Academy Awards ceremony honors the best of the best in acting, directing, original screenplays, motion pictures, and more.

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27. Quincy (2018)

“Quincy” delves into the life of the legendary music and cultural icon, Quincy Jones. As a pioneer in both music and popular culture for 70 years, Jones’ story is deeply interwoven with the history of America. With a career spanning decades, Jones transcends racial and cultural boundaries, earning him the nickname “the Renaissance Man of pop. “ This riveting documentary not only gives an intimate look into the life of this iconic figure but also sheds light on the impact he has had on shaping the course of American music and culture.

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28. Pizza: A Love Story (2019)

“The Art of Pizza: A Heartfelt Journey” is a fascinating documentary (2019, 1 hour and 25 minutes) that invites viewers to dive into a culinary adventure by exploring the rich history, dedication, and craftsmanship that goes into creating each exquisitely handcrafted pizza. This authentic tale presents the heart and soul behind the making of genuine Italian pizzas, challenging our understanding of food and its cultural impact.

📺 Watch now free at Amazon

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