The Best Frank Sinatra Movies

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Updated November 5, 2024 73.0K views 69 items

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Achieving great new heights in the realm of film, Frank Sinatra had an exceptional career in which he portrayed memorable characters that continue to inspire generations of film fans. With an array of awe-inspiring performances, this singer and actor sent reverberations throughout the world of entertainment, packing a punch that's impossible to ignore even today. From romantic dramas to suspense thrillers, every Sinatra appearance leaves a lingering impression, each being a testament to the unmatched versatility and talent of this legendary figure. It's all here, a meandering journey through the best Frank Sinatra movies every film enthusiast must experience.

Each narrative unfolds with a magnetic allure, sweeping audiences off their feet as the remarkable charisma and talent of Sinatra permeate the silver screen. With flawless performances etched into cinematic history, these movies with Frank Sinatra serve as monuments to his acting prowess. Beyond showcasing the actor himself, these films also illustrate the incredible quality of Hollywood productions of the day. The directorial genius, innovative storytelling, and spellbinding performances enchant viewers, making it clear why these Frank Sinatra films are held in such high regard.

Take From Here to Eternity, for instance. Sinatra's stirring depiction of Private Angelo Maggio leaves viewers enthralled, earning praise and accolades including an Academy Award. Similarly, The Manchurian Candidate brims with suspense, as Sinatra's compelling performance weaves a web of intrigue that's hard to escape. Equally noteworthy is The Man with the Golden Arm. Sinatra's harrowing portrayal of a drug addict in turmoil elicits empathy while underscoring the harsh realities of addiction. These samples from the list of the vast collection of Frank Sinatra movies represent the mosaic of storytelling styles and characters he brought to life, each a unique testament to Sinatra's range and skill.

The best Frank Sinatra movies are not just tales narrated through celluloid, but evocative sagas that encapsulate the heart and soul of Hollywood's golden era. The myriad movies in which Frank Sinatra performed expanded to many genres and eras, taking the viewers on a fascinating journey. The grandeur of these films is testimony to Sinatra's colossal talent, each movie leaving an indelible mark on the sands of cinematic time, illustrating the actor's timeless appeal and seductive charm. That's why the best Frank Sinatra movies remain an essential part of film history - a treasure trove of masterpieces worthy of every cinephile's time and admiration.

1
The Manchurian Candidate
Frank Sinatra, Laurence Harvey, Janet Leigh
231 votes
This chilling political thriller follows the story of a former prisoner of war who is brainwashed into becoming an unwitting assassin for an international conspiracy. Sinatra commands the screen as Maj. Bennett Marco, whose unraveling of the plot fuels the film's tension and suspense. The film's combination of psychological intrigue and Cold War paranoia has secured its status as a critical and commercial success, proving Sinatra's versatility as both an actor and singer.
- Released: 1962
- Directed by: John Frankenheimer
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2
From Here to Eternity
Burt Lancaster, Montgomery Clift, Deborah Kerr
236 votes
A wartime drama filled with romance and tragedy, this film explores the experiences of a group of soldiers stationed in Hawaii before the attack on Pearl Harbor. Sinatra delivers a powerful performance as Private Angelo Maggio, showcasing his range as an actor and earning him an Academy Award for Best Supporting Actor. The film's compelling narrative and strong performances from its ensemble cast make it an enduring classic, highlighting Sinatra's ability to captivate audiences with his on-screen presence.
- Released: 1953
- Directed by: Fred Zinnemann
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3
The Man with the Golden Arm
Frank Sinatra, Eleanor Parker, Kim Novak
195 votes
A gritty and unflinching look at the life of a drug addict struggling to reform, this film showcases Sinatra's dramatic acting chops as he portrays protagonist Frankie Machine. Sinatra's harrowing portrayal of addiction earned him rave reviews and respect as a serious actor beyond his fame as a singer. The film's bold subject matter and willingness to confront the realities of drug abuse paved the way for more open discussions of addiction in cinema, making it a significant moment in Sinatra's acting career.
- Released: 1955
- Directed by: Otto Preminger
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4
Von Ryan's Express
Frank Sinatra, Trevor Howard, Brad Dexter
191 votes
An action-packed war film, this movie follows the daring escape of Allied POWs from a Nazi-controlled prison camp during World War II. Sinatra brings gravitas and charisma to the role of Colonel Joseph L. Ryan, an American pilot leading the escape effort. The film's thrilling blend of suspense and adventure made it a box office hit while solidifying Sinatra's reputation as a leading man.
- Released: 1965
- Directed by: Mark Robson
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5
High Society
Bing Crosby, Grace Kelly, Frank Sinatra
188 votes
This romantic musical comedy takes place among the glitz and glamour of Newport high society, with Sinatra shining as jaded reporter Mike Connor. His effortless charm and smooth voice are showcased in memorable musical numbers, adding to the film's effervescent atmosphere. High Society's winning blend of romance, humor, and unforgettable songs has secured its spot as a beloved classic that highlights Sinatra's undeniable star power.
- Released: 1956
- Directed by: Charles Walters
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6
Some Came Running
Frank Sinatra, Dean Martin, Shirley MacLaine
133 votes
Set against the backdrop of small-town America, this drama chronicles the story of a disillusioned writer who returns to his hometown after World War II. Sinatra delivers a nuanced performance as Dave Hirsh, the conflicted protagonist grappling with his past and present. The film's exploration of postwar disillusionment and personal growth garnered critical acclaim, proving that Sinatra's talent extended beyond his crooning abilities.
- Released: 1958
- Directed by: Vincente Minnelli
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7
Pal Joey
Rita Hayworth, Frank Sinatra, Kim Novak
173 votes
In this screen adaptation of the beloved Broadway musical, Sinatra captivates audiences as the charmingly unscrupulous nightclub singer Joey Evans. His magnetic performance is bolstered by the unforgettable score, which includes now-iconic songs like "The Lady Is a Tramp." Pal Joey's critical and commercial success cemented Sinatra's status as a major star in both film and music.
- Released: 1957
- Directed by: George Sidney
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8
The Devil at 4 O'Clock
Spencer Tracy, Frank Sinatra, Kerwin Mathews
85 votes
This disaster film follows the story of three convicts and a priest attempting to save a group of children from an erupting volcano on a remote island. Sinatra brings a sense of vulnerability and intensity to the role of convict Harry, providing a human element amidst the film's action-packed narrative. The Devil at 4 O'Clock's thrilling plot and engaging characters have made it a cult favorite among disaster movie enthusiasts.
- Released: 1961
- Directed by: Mervyn LeRoy
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9
Young at Heart
Doris Day, Frank Sinatra, Gig Young
125 votes
A warm and tender family drama centered around three sisters who fall for the same charming songwriter, this film is enlivened by Sinatra's magnetic portrayal of Barney Sloan. His sensitive performance and effortless charm endeared him to audiences, showcasing his versatility as an actor. Young at Heart's blend of romance, familial bonds, and heartfelt musical numbers ensured its success both critically and commercially.
- Released: 1954
- Directed by: Gordon Douglas
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10
Anchors Aweigh
Frank Sinatra, Gene Kelly, Kathryn Grayson
139 votes
An energetic musical comedy set in Hollywood, this film follows two sailors on leave as they navigate the movie industry and a whirlwind romance. Sinatra demonstrates his triple-threat talents as singing, dancing, and acting sailor Clarence Doolittle. The film's infectious energy and memorable musical sequences earned it several Academy Award nominations, showcasing Sinatra's versatility and talent.
- Released: 1945
- Directed by: George Sidney
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11
The Detective
Frank Sinatra, Lee Remick, Jacqueline Bisset
134 votes
In this gritty crime drama, Sinatra brings depth and intensity to the role of Joe Leland, a determined police detective investigating a high-profile murder case. His compelling performance helps to elevate the film beyond its pulpy origins, earning the respect of audiences and critics alike. The Detective's suspenseful plot and engaging characterizations have made it a cult favorite among cinema enthusiasts.
- Released: 1968
- Directed by: Gordon Douglas
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12
Suddenly
Frank Sinatra, Sterling Hayden, James Gleason
115 votes
This taut thriller follows a group of assassins plotting to assassinate the President of the United States in the sleepy town of Suddenly, California. Sinatra's chilling performance as the unhinged John Baron helped to elevate the film beyond its B-movie origins. The film's tense atmosphere and unexpected twists have made it a cult favorite, earning praise for Sinatra's skill as a serious dramatic actor.
- Released: 1954
- Directed by: Lewis Allen
13
Ocean's 11
Frank Sinatra, Dean Martin, Sammy Davis
219 votes
This stylish, star-studded heist film follows a group of World War II veterans as they plan to rob five Las Vegas casinos in a single night. Sinatra's commanding presence in the role of ringleader Danny Ocean drives the film's slick, fast-paced narrative. Ocean's 11's blend of suspense, humor, and sleek production values has immortalized it as a seminal crime caper, setting the stage for numerous sequels and spin-offs.
- Released: 1960
- Directed by: Lewis Milestone
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14
The Joker Is Wild
Frank Sinatra, Mitzi Gaynor, Jeanne Crain
111 votes
Based on the true-life story of comedian Joe E. Lewis, this film charts the rise and fall of a gifted performer whose career is derailed by a vicious attack. Sinatra's heartfelt portrayal of the troubled entertainer earned him critical praise, showcasing his adeptness at playing complex characters. The film's captivating blend of drama and humor ensures its enduring appeal, while Sinatra's performance highlights his impressive acting range.
- Released: 1957
- Directed by: Charles Vidor
15
Guys and Dolls
Marlon Brando, Jean Simmons, Frank Sinatra
176 votes
In this big-screen adaptation of the Broadway musical, Sinatra shines as the charismatic gambler Nathan Detroit. His undeniable charm and smooth singing voice help to bring the character to life, resulting in a memorable performance. The film's lavish production values, energetic musical numbers, and vibrant performances have made Guys and Dolls a favorite among cinema lovers and fans of the stage show alike.
- Released: 1955
- Directed by: Joseph L. Mankiewicz
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16
On the Town
Gene Kelly, Frank Sinatra, Ann Miller
139 votes
An exuberant musical about three sailors on leave in New York City, this film showcases Sinatra's impeccable comedic timing and delightful singing as Chip, one of the sailors. With its infectious energy, memorable songs, and captivating performances from the ensemble cast, On the Town has become an enduring classic in the genre, cementing Sinatra's reputation as a multi-talented entertainer.
- Released: 1949
- Directed by: Stanley Donen, Gene Kelly
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17
The Tender Trap
Debbie Reynolds, Frank Sinatra, David Wayne
110 votes
A delightful romantic comedy centered around a talent agent who juggles the affections of several women, this film showcases Sinatra's effortless charm as protagonist Charlie Reader. His engaging performance imbues the character with warmth and likability, while the witty script and lively musical numbers ensure the film's enduring appeal. The Tender Trap's combination of romance, humor, and memorable songs has cemented its status as a classic comedy.
- Released: 1955
- Directed by: Charles Walters
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18
Robin and the Seven Hoods
Frank Sinatra, Dean Martin, Sammy Davis
139 votes
A musical crime comedy set in Prohibition-era Chicago, this film stars Sinatra as gangster Robbo, who becomes embroiled in a turf war with rival mobsters. His smooth crooning and engaging performance make Robbo a memorable character, while the stylish production values and toe-tapping musical numbers ensure the film's lasting appeal. Robin and the Seven Hoods' blend of comedy, drama, and engaging performances has made it a favorite among fans of both Sinatra and the Rat Pack.
- Released: 1964
- Directed by: Gordon Douglas
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19
None but the Brave
Frank Sinatra, Clint Walker, Tony Bill
110 votes
A gripping war drama centered around a group of stranded American and Japanese soldiers on a deserted island, this film showcases Sinatra's ability to convey both vulnerability and strength as Lt. Kuroki. His poignant performance is complemented by the film's exploration of themes such as honor, comradeship, and the shared humanity of enemies. None but the Brave's engaging narrative and powerful performances ensure its lasting impact on both critics and audiences.
- Released: 1965
- Directed by: Frank Sinatra
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20
A Hole in the Head
Frank Sinatra, Edward G. Robinson, Eleanor Parker
105 votes
A warmhearted comedy about a hapless widower grappling with financial woes and parental responsibilities, this film is anchored by Sinatra's charming portrayal of Tony Manetta. His heartfelt performance lends the character a relatable humanity, while the film's colorful supporting cast and memorable musical numbers make it a delightful cinematic experience. A Hole in the Head's winning blend of humor, sentiment, and unforgettable songs ensures its appeal for generations of viewers.
- Released: 1959
- Directed by: Frank Capra
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21
Kings Go Forth
Frank Sinatra, Tony Curtis, Natalie Wood
75 votes
This World War II drama focuses on the complex relationships between two soldiers and the French woman they both fall in love with. Sinatra brings depth and nuance to the role of Sgt. Loggins, showcasing his skill as a dramatic actor. The film's exploration of racial prejudice and romantic entanglements, along with its strong performances, make it a compelling and thought-provoking watch.
- Released: 1958
- Directed by: Delmer Daves
22
Tony Rome
Frank Sinatra, Jill St. John, Richard Conte
117 votes
In this stylish detective thriller, Sinatra stars as the eponymous private investigator tasked with solving a high-profile murder case. His charismatic performance and distinctive style imbue the character with a sense of cool that has become synonymous with the genre. Tony Rome's captivating plot and unforgettable characters have made it a beloved addition to classic detective film canon.
- Released: 1967
- Directed by: Gordon Douglas
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23
The Miracle of the Bells
Frank Sinatra, Fred MacMurray, Lee J. Cobb
44 votes
In this touching drama, Sinatra plays a press agent tasked with promoting a starlet who dies suddenly after completing her first film. His tender and emotional performance highlights his ability to connect with audiences on a deeper level. The Miracle of the Bells' heartfelt narrative and strong performances make it a powerful and memorable film.
- Released: 1948
- Directed by: Irving Pichel
24
Never So Few
Frank Sinatra, Gina Lollobrigida, Peter Lawford
69 votes
This World War II film delves into the complex relationships, loyalties, and moral dilemmas faced by soldiers stationed in Burma during the conflict. Sinatra delivers a compelling performance as Captain Tom Reynolds, a committed officer grappling with difficult decisions. The film's exploration of ethical quandaries and strong performances make it a noteworthy entry in the war movie genre.
- Released: 1959
- Directed by: John Sturges
- Also ranks #23 on The Best Steve McQueen Movies, Ranked
- Also ranks #56 on The Best Charles Bronson Movies
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25
Take Me Out to the Ball Game
Gene Kelly, Frank Sinatra, Esther Williams
79 votes
A delightful musical comedy set in the world of professional baseball, this film features Sinatra as a singing and dancing shortstop who falls for a beautiful team owner. His natural charm and sparkling chemistry with the rest of the ensemble cast make for an entertaining, lighthearted romp. With its catchy songs and engaging narrative, Take Me Out to the Ball Game has remained a fan favorite for decades.
- Released: 1949
- Directed by: Busby Berkeley
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26
The First Deadly Sin
Frank Sinatra, Faye Dunaway, David Dukes
63 votes
A tense crime thriller that follows a detective's obsessive pursuit of a brutal serial killer, this film showcases Sinatra's gritty performance as the dedicated and hardened Detective Edward Delaney. His portrayal of the character's dogged determination adds an intensity to the compelling narrative. The First Deadly Sin's suspenseful plot and Sinatra's commanding performance make it an enduring favorite among crime drama fans.
- Released: 1980
- Directed by: Brian G. Hutton
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27
Come Blow Your Horn
Frank Sinatra, Lee J. Cobb, Molly Picon
76 votes
In this vibrant adaptation of Neil Simon's hit play, Sinatra shines as a swinging bachelor who attempts to teach his younger brother the art of romance and independence. His comedic timing, wit, and undeniable charm are on full display, making his performance a standout among the ensemble cast. The film's winning combination of humor, relatable family dynamics, and strong performances ensures its lasting appeal as an enjoyable comedy.
- Released: 1963
- Directed by: Bud Yorkin
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28
The Pride and the Passion
Cary Grant, Frank Sinatra, Sophia Loren
66 votes
An epic historical drama set during the Napoleonic Wars, this film follows a multinational group attempting to transport a massive cannon across Spain. Sinatra brings passion and intensity to his role as Miguel, a Spanish guerrilla fighter. The film's grand scale, powerful performances, and exploration of themes such as loyalty and sacrifice have made it a standout in the historical drama genre.
- Released: 1957
- Directed by: Stanley Kramer
29
Can-Can
Frank Sinatra, Shirley MacLaine, Maurice Chevalier
58 votes
Set in turn-of-the-century Paris, this lively musical comedy focuses on the romantic escapades of a nightclub owner and her lawyer. Sinatra shines as the charismatic attorney François Durnais, adding his smooth singing voice and charm to the role. Can-Can's vibrant atmosphere, memorable songs, and engaging performances have made it a beloved classic that highlights Sinatra's multifaceted talent.
- Released: 1960
- Directed by: Walter Lang
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30
Lady in Cement
Frank Sinatra, Raquel Welch, Dan Blocker
71 votes
In this crime drama sequel to Tony Rome, Sinatra reprises his role as the suave private investigator to solve the murder of a woman found encased in cement. His charisma and style continue to captivate audiences as he navigates the seedy underworld of Miami. Lady in Cement's blend of action, intrigue, and memorable characters makes it a worthy follow-up to the original film.
- Released: 1968
- Directed by: Gordon Douglas
31
It Happened in Brooklyn
Frank Sinatra, Kathryn Grayson, Peter Lawford
48 votes
This heartwarming musical romance follows a disillusioned soldier returning home from World War II, played by Sinatra, as he navigates love and life in postwar Brooklyn. His charming performance and captivating singing voice make for an enjoyable and unforgettable film experience. It Happened in Brooklyn's nostalgic atmosphere, memorable songs, and touching narrative have made it a favorite among fans of classic cinema.
- Released: 1947
- Directed by: Richard Whorf
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32
Sergeants 3
Frank Sinatra, Dean Martin, Sammy Davis
75 votes
In this comedic western, Sinatra stars as Sgt. Mike Merry, a member of the Cavalry fighting to protect a frontier town from fierce Native American warriors. Sinatra's talent for blending humor, action, and drama is on full display in this entertaining adventure film. Sergeants 3's lively ensemble cast, engaging narrative, and expert mix of comedy and action have made it a fun addition to the western genre.
- Released: 1962
- Directed by: John Sturges
33
Marriage on the Rocks
Frank Sinatra, Deborah Kerr, Dean Martin
61 votes
A lighthearted comedy that explores the complications arising from a mistaken divorce and remarriage, this film features Sinatra as the hapless husband caught in the middle of the confusion. His comedic timing and effortless charm bring levity to the entertaining and chaotic story. Marriage on the Rocks' blend of humor, romance, and engaging performances make it an enjoyable watch.
- Released: 1965
- Directed by: Jack Donohue
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34
The House I Live In
Frank Sinatra
41 votes
In this powerful short film, Sinatra uses his voice and influence to advocate against racial and religious intolerance. His passionate performance conveys the importance of understanding and unity in a divided world. The House I Live In's timely message and Sinatra's commitment to social justice make it a poignant and significant part of his legacy.
- Released: 1945
- Directed by: Mervyn LeRoy
35
Frank Sinatra: Sinatra in Concert at Royal Festival Hall
Frank Sinatra
62 votes
In this live concert event, Sinatra captivates audiences with an unforgettable performance showcasing his immense talent as a singer and entertainer. The concert film provides a rare opportunity for viewers to witness the legend in action, performing classic songs and engaging with the audience. This performance is a testament to Sinatra's enduring status as one of the greatest entertainers of all time.
- Released: 1971
- Directed by: Bill Miller
36
Frank Sinatra: The Main Event
Frank Sinatra
38 votes
This televised concert special captures Sinatra in his element, performing live at the legendary Madison Square Garden. Dazzling audiences with his incomparable vocal talents and charismatic stage presence, the concert is a testament to Sinatra's enduring legacy as an entertainer. The Main Event offers a rare and intimate glimpse into the magic of Sinatra's live performances, making it a must-see for fans and music aficionados alike.
- Released: 1974
- Directed by: Bill Carruthers
37
4 for Texas
Frank Sinatra, Dean Martin, Anita Ekberg
77 votes
This western comedy follows two rival conmen who reluctantly join forces to save a struggling riverboat casino. Sinatra brings his signature blend of charisma and humor to the role of gambler Zack Thomas. The film's mix of lighthearted comedy and action-packed adventure makes it an entertaining entry in Sinatra's filmography.
- Released: 1963
- Directed by: Robert Aldrich
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38
Meet Danny Wilson
Frank Sinatra, Shelley Winters, Raymond Burr
38 votes
In this dramatic musical, Sinatra plays a struggling nightclub singer whose fortunes change when he teams up with a ruthless gangster. His emotionally charged performance and unforgettable singing voice bring depth and complexity to the character. Meet Danny Wilson's captivating blend of drama, romance, and music has made it an enduring classic.
- Released: 1951
- Directed by: Joseph Pevney
39
Francis Albert Sinatra Does His Thing
34 votes
In this 1968 television special, Sinatra dazzles audiences with a unique blend of musical performances, skits, and dramatic scenes. The special showcases his range as a performer and his ability to captivate viewers with his singular talent. Francis Albert Sinatra Does His Thing solidifies the entertainer's status as a true icon and master of his craft.
- Released: 1968
40
Anything Goes
Frank Sinatra, Dean Martin, Ethel Merman
33 votes
In this lively adaptation of the hit Broadway musical, Sinatra shines as the charming and mischievous Billy Crocker. His natural charisma, comedic timing, and smooth singing voice make his performance a memorable one. The film's infectious energy, memorable songs, and engaging performances have made Anything Goes a fan favorite.
- Released: 1954
- Directed by: Peter Barnum
41
Not as a Stranger
Frank Sinatra, Olivia de Havilland, Robert Mitchum
37 votes
In this medical drama, Sinatra co-stars as a dedicated but struggling surgeon grappling with questions of ethics and professionalism. His heartfelt performance as Dr. Alfred Boone adds emotional weight to the film's examination of the challenges faced by medical professionals. Not as a Stranger's compelling narrative and strong ensemble cast make it an important exploration of the human experience.
- Released: 1955
- Directed by: Stanley Kramer
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42
Live and Swingin': The Ultimate Rat Pack Collection
Frank Sinatra, Dean Martin, Sammy Davis
32 votes
A documentary exploring the life and work of composer Cole Porter, featuring interviews and performances by various artists, including Frank Sinatra.
- Released: 1965
- Also ranks #24 on The 25+ Best Sammy Davis, Jr. Movies
- Also ranks #46 on All Dean Martin Movies List, Ranked
43
Assault on a Queen
Frank Sinatra, Virna Lisi, Anthony Franciosa
44 votes
This action-adventure film centers around a daring heist to hijack a luxury cruise liner using a retired WWII U-boat. Sinatra brings his commanding presence to the role of mastermind Mark Brittain, driving the suspenseful narrative. Assault on a Queen's unique blend of action, adventure, and intrigue make it an entertaining entry in Sinatra's diverse filmography.
- Released: 1966
- Directed by: Jack Donohue
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44
A Bing Crosby Christmas
Frank Sinatra, Carol Burnett
31 votes
In this festive television special, Sinatra joins the legendary crooner for a heartwarming celebration of the holiday season. Their combined talents and charm create a memorable and joyous experience for viewers. A Bing Crosby Christmas's harmonious blend of music, camaraderie, and seasonal cheer make it a beloved classic.
- Released: 2000
45
Hollywood Musicals of the '60s
Frank Sinatra
17 votes
A documentary that reviews and compiles various Hollywood musical productions from the 1960s, highlighting notable performances and significant films from that era, including appearances by Frank Sinatra.
- Released: 1999
46
Cast a Giant Shadow
Kirk Douglas, Senta Berger, Angie Dickinson
38 votes
This historical war drama focuses on the efforts of American military advisor Colonel David "Mickey" Marcus to help the fledgling state of Israel during its 1948 War of Independence. Sinatra makes a memorable cameo appearance as a fighter pilot, showcasing his versatility as both a dramatic and comedic actor. The film's epic scope, powerful performances, and engaging narrative have made Cast a Giant Shadow a standout in the war movie genre.
- Released: 1966
- Directed by: Melville Shavelson
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47
Double Dynamite
Frank Sinatra, Jane Russell, Groucho Marx
24 votes
Johnny Dalton (Frank Sinatra), a poor bank teller who works tirelessly to save enough money to marry his doting girlfriend (Jane Russell), comes across a fortune when he rescues a duplicitous bookie (Nestor Paiva) from attackers. As a misguided sign of thanks, the bookie gives Dalton an ample cash gift -- which curiously matches the amount missing from his bank. Now suspected of embezzlement, the bewildered Dalton turns to his best friend, a wily and wacky waiter (Groucho Marx), for help.
- Released: 1951
- Directed by: Irving Cummings
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48
Road to Victory
Frank Sinatra, Cary Grant, Bing Crosby
22 votes
Road to Victory is a 1944 short film notable for being with Bing Crosby, a major singing and movie star, Cary Grant a major actor in motion pictures and a new singer of the time who would also be a movie figure Frank Sinatra. The short also featured Benny Goodman and Harry James. The movie was an edited and truncated re-release of The Shining Future from the same year.
- Released: 1944
- Also ranks #44 on The Best Cary Grant Movies, Ranked
- Also ranks #48 on The Best Bing Crosby Movies, Ranked
49
You're the Top: The Cole Porter Story
Frank Sinatra, Bob Hope, Bobby Short
32 votes
A documentary exploring the life and work of composer Cole Porter, featuring interviews and performances by various artists, including Frank Sinatra.
- Released: 1990
50
Milton Berle's Buick Hour #4
Frank Sinatra, Sid Caesar, Vic Damone
18 votes
A 1954 television special hosted by Milton Berle featuring performances from various entertainers, including Frank Sinatra.
- Released: 1954
51
That's Entertainment!
Elizabeth Taylor, Liza Minnelli, Mickey Rooney
37 votes
A loving tribute to the golden age of Hollywood, this documentary features Sinatra as one of the many stars celebrating the history of American cinema. His charismatic presence highlights the impact he made on the film industry during his illustrious career. That's Entertainment!'s nostalgic celebration of movie magic ensures its status as a beloved ode to a bygone era.
- Released: 1974
- Directed by: Jack Haley
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52
Upbeat in Music
Frank Sinatra, Benny Goodman, Duke Ellington
18 votes
Upbeat in Music is a 1943 film short produced as part of The March of Time series distributed theatrically by 20th Century Fox. The film has significant history as being early film appearances of Frank Sinatra and Perry Como. The film also features footage of Glenn Miller in uniform as a Captain in the U.S. Air Force leading the U.S. Army Training Command Band.
- Released: 1943
53
Contract on Cherry Street
Frank Sinatra, Martin Balsam, Michael Nouri
28 votes
A gritty crime drama, this television film showcases Sinatra as a dedicated police detective seeking justice for his murdered partner. His intense performance and commitment to the character make for an engaging and suspenseful viewing experience. Contract on Cherry Street's thrilling plot and Sinatra's skillful acting make it a worthwhile addition to the crime drama genre.
- Released: 1977
- Directed by: William A. Graham
54
Higher and Higher
Michèle Morgan, Jack Haley, Frank Sinatra
30 votes
On the verge of losing his home, former millionaire Cyrus (Leon Errol) and his driver, Mike (Jack Haley), recruit Millie (Michele Morgan), a beautiful maid, to pose as the fictitious heiress to Cyrus' now-spent fortune. With Mike's guidance, Millie courts the debonair Sir Victor Fitzroy (Victor Borge) in hopes of marrying him to obtain a dowry. But Victor may not be what he seems, neighborhood kid Frank (Frank Sinatra) wants Millie for himself -- and poor Millie doesn't love either of them.
- Released: 1943
- Directed by: Tim Whelan
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55
The Naked Runner
Frank Sinatra, Edward Fox, Peter Vaughan
22 votes
The Naked Runner is a 1967 British espionage film directed by Sidney J. Furie and starring Frank Sinatra, Peter Vaughan, Edward Fox. It was the last film Sinatra made with Warner Bros. and is largely viewed as being a fairly disastrous end to his association with the studio.
- Released: 1967
- Directed by: Sidney J. Furie
56
Dirty Dingus Magee
Frank Sinatra, George Kennedy, Anne Jackson
44 votes
While traveling in New Mexico, Hoke Birdsill (George Kennedy) is robbed by Dirty Dingus Magee (Frank Sinatra), a bumbling criminal. So when Hoke arrives in the nearest town, Yerkey's Hole, he demands justice from Belle Nops (Anne Jackson), the town's mayor and the madam of the local bordello. In response, Belle deputizes Hoke. Despite Hoke's best efforts, however, Dirty Dingus Magee continues to stir up trouble, aided by his American Indian lover, Anna Hot Water (Michele Carey).
- Released: 1970
- Directed by: Burt Kennedy
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57
The List of Adrian Messenger
George C. Scott, Dana Wynter, Clive Brook
34 votes
British army Col. Anthony Gethryn (George C. Scott) is contacted by his old friend, Adrian Messenger (John Merivale), to investigate 11 men, whose names Messenger provides. After a plane carrying Messenger is blown up by a mysterious perpetrator, Gethryn determines that the men on the list had been prisoners of war in Burma during World War II -- and that someone connected to a minor British aristocrat (Clive Brook) is methodically murdering each man on the list.
- Released: 1963
- Directed by: John Huston
58
Around the World in 80 Days
David Niven, Cantinflas, Shirley MacLaine
37 votes
In this epic adventure film based on Jules Verne's classic novel, Sinatra makes a memorable cameo as a saloon pianist during the protagonists' journey around the globe. His charismatic performance adds a touch of humor and whimsy to the thrilling story. Around the World in 80 Days' grand scale, inventive narrative, and memorable cameo appearances, including Sinatra's, make it a beloved classic in the adventure genre.
- Released: 1956
- Directed by: Michael Anderson
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59
La Classe américaine
Elvis Presley, Frank Sinatra, Dustin Hoffman
20 votes
La Classe américaine, also known as Le Grand Détournement, is a 1993 French television film, written and directed by Michel Hazanavicius and Dominique Mézerette. It consists exclusively of extracts of old Warner Bros. films, put together and dubbed with new lines so as to create an entirely new film.
- Released: 1993
- Directed by: Dominique Mezerette, Michel Hazanavicius
60
Till the Clouds Roll By
Robert Walker, Van Heflin, Lucille Bremer
28 votes
This musical biopic of composer Jerome Kern features a star-studded ensemble cast, including Sinatra, who lends his voice to the film's memorable soundtrack. His smooth singing and charismatic presence contribute to the film's tribute to one of America's most influential songwriters. Till the Clouds Roll By's celebration of music, history, and the life of a beloved composer make it a favorite among fans of classic cinema.
- Released: 1946
- Directed by: Richard Whorf
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61
Listen Up! The Lives of Quincy Jones
Frank Sinatra, Miles Davis, Quincy Jones
24 votes
A documentary exploring the life and career of Quincy Jones, featuring performances and interviews with various artists, including Frank Sinatra.
- Released: 1990
- Directed by: Ellen Weissbrod
62
Step Lively
Frank Sinatra, George Murphy, Adolphe Menjou
23 votes
Producer Gordon Miller (George Murphy) and his profligate actors are staying at a New York City hotel, where they're living the high life as they plan to mount a stage show. Alas, they have no money to pay their bills, and hotel boss Wagner (Adolphe Menjou) will banish them unless he gets paid. Joining the parade of those about to be bilked by Miller is Glenn Russell (Frank Sinatra), a playwright whose stellar singing just might be enough to right the fortunes of all involved.
- Released: 1944
- Directed by: Tim Whelan
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63
World's Greatest Movie Challenge
Frank Sinatra, Kirk Douglas, Bob Hope
21 votes
A 1988 special featuring various celebrities, including Frank Sinatra, participating in a series of cinematic challenges.
- Released: 1988
64
Johnny Concho
Frank Sinatra, Keenan Wynn, William Conrad
23 votes
The people of Cripple Creek fear Johnny Concho (Frank Sinatra), but only because his brother is a notorious gunfighter. Johnny takes advantage of his position, bullying the townsfolk, until the arrival of a cowboy named Tallman (William Conrad). Tallman claims to have killed Johnny's brother and, after exposing Johnny as a coward, takes over the town. Tallman, however, is more hated than Johnny. Johnny must now gain the courage to fight Tallman and earn the respect of Cripple Creek.
- Released: 1956
- Directed by: Don McGuire
65
Cannonball Run II
Burt Reynolds, Dom DeLuise, Shirley MacLaine
37 votes
When a sheik (Jamie Farr) decides to sponsor a cross-country race in hope of winning, racer J.J. McLure (Burt Reynolds) enters the competition along with his friend Victor (Dom DeLuise). They aspire to claim the $1 million prize and pick up two women on the way. Meanwhile, the sheik helps Jamie Blake (Dean Martin) and Morris Fenderbaum (Sammy Davis Jr.) with an angry mob boss. But when the sheik is kidnapped, the contestants must come together to help him.
- Released: 1984
- Directed by: Hal Needham
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66
Step Lively
Frank Sinatra, Harold Lloyd, George Murphy
21 votes
Step Lively is a 1917 American short comedy film featuring Harold Lloyd. A print of the film at the UCLA Film and Television Archive.
- Released: 1917
- Directed by: Tim Whelan, Alfred J. Goulding
67
The Kissing Bandit
Frank Sinatra, Kathryn Grayson, J. Carrol Naish
23 votes
In the 19th century, Ricardo (Frank Sinatra) is a hotel keeper in Spanish-ruled California. But his father did something decidedly different, once masquerading as an outlaw called the "Kissing Bandit" because he planted a smooch on women after robbing them. Ricardo doesn't know this, though, until his dad's former partner, Chico (J. Carrol Naish), finds the young man and tells him the story, eventually getting Ricardo to follow in his dad's footsteps and become an outlaw.
- Released: 1948
- Directed by: Laslo Benedek
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68
Yours for a Song: The Women of Tin Pan Alley
9 votes
A story of the women who created some of Broadway's most memorable songs.
- Released: 1999
- Directed by: Terry Benes
69
The Legendary Bing Crosby
11 votes
A documentary examining the life and career of singer and actor Bing Crosby, with contributions from Frank Sinatra.
- Released: 2009