December 12th marks what would have been Frank Sinatra's 108th birthday. Sinatra is unquestionably one of the twentieth century's greatest entertainers. One of the highest-selling musical artists of all time, Sinatra's record sales surpassed over 150 million. In the late 1990s, Time magazine included Sinatra on their list of the 100 most influential people of the twentieth century. Famed music critic Robert Christgau named Sinatra the best singer of the twentieth century.

However, a gravely underrated aspect of Sinatra's career is his acting prowess. Not only is Sinatra an icon of the music industry, but he is also one of Hollywood's premier stars. Many of Sinatra's finest performances rank among cinema's most memorable movie roles.

10 Anchors Aweigh Was Sinatra's First Role Of Prominence (1945)

• IMDb Rating: 7.0

Sinatra's first film role of prominence, Anchors Aweigh was the first of three musical comedies that teamed Sinatra with Gene Kelly. In the film, Sinatra and Kelly play two Navy sailors on leave who decide to help a movie extra become a musical star.

Anchors Aweigh was one of the highest-grossing films of 1945 and earned five Academy Award nominations, winning Best Music, Scoring of a Musical Picture. In 2006, the American Film Institute nominated Anchors Aweigh for its list of the greatest Hollywood musicals. Although Anchors Aweigh's most famous sequence is the dance routine between Kelly and Jerry Mouse, Sinatra has an equally notable sequence of his own. Sinatra debuted the song "I Fall in Love Too Easily," which earned an Oscar nomination for Best Original Song. The song eventually became a jazz standard in the Great American Songbook.

9 On The Town Is The Best Of The Sinatra/Kelly Musicals (1949)

• IMDb Rating: 7.3

The best and final of the Sinatra/Kelly musicals, On the Town, was the directorial debut of Kelly and Stanley Donen. The two would go on to co-direct Singin' in the Rain, the greatest of all Hollywood musicals. In On the Town, Sinatra and Kelly co-star alongside Jules Munshin as three Navy sailors who cause havoc as they search for love while on leave in New York City.

On the Town won the Academy Award for Best Music, Scoring of a Musical Picture. Retrospectively, On the Town placed 19th on the American Film Institute's list of the greatest musicals, and in 2018, the film entered the National Film Registry for its importance to American film history. In the film, Sinatra, Kelly, and Munshin sing "New York, New York," a song voted the 41st best movie song of all time by the American Film Institute. While many of Sinatra's later film roles swayed toward drama, these early musical film performances displayed his command of comedy.

8 Frank Sinatra Was The Original Danny Ocean In Ocean's Eleven (1960)

• IMDb Rating: 6.5

While modern audiences know the Ocean's film series as a blockbuster franchise, the original Ocean's Eleven was a starring vehicle for the Rat Pack, an informal group of entertainers that in the early 1960s consisted of Sinatra, Dean Martin, Sammy Davis Jr., Joey Bishop, and Peter Lawford. Sinatra originated the role of Danny Ocean, who in the film recruits a group of his World War II buddies to commit the ultimate heist; robbing five Las Vegas casinos at once.

The Rat Pack's legacy is synonymous with Las Vegas and Ocean's Eleven astutely captures the uncanny chemistry that existed between these legendary pop culture figures. As Danny Ocean, Sinatra demonstrates why he was the leader of The Rat Pack with a suave, confident, and commanding performance. For Steven Soderbergh's Ocean's trilogy, George Clooney assumed the role of Danny Ocean.

7 Pal Joey Earned Sinatra A Golden Globe (1957)

• IMDb Rating: 6.6

A cinematic adaptation of the 1940 Rodgers and Hart play of the same name, Pal Joey is a musical starring Sinatra alongside Rita Hayworth and Kim Novak. In the film, Sinatra plays Joey Evans, an opportunistic singer who woos a wealthy widow to boost his career.

Pal Joey was a box office hit, finishing the year as one of the ten highest-grossing films. Critically, Pal Joey earned four Academy Award nominations, while at the Golden Globes, Sinatra won Best Actor - Comedy or Musical. Sinatra also won the Laurel Award for Top Male Musical Performance. The New York Times praised Sinatra's performance, highlighting his renditions of "The Lady is a Tramp" and "There's a Small Hotel" as some of the film's best sequences. The American Film Institute nominated Pal Joey for its list of the greatest musicals.

6 Guys And Dolls Is Sinatra's Best Musical Performance (1955)

• IMDb Rating: 7.1

Based on the Tony Award-winning musical of the same name, Joseph L. Mankiewicz's Guys and Dolls stars Sinatra as Nathan Detroit, a gambler who needs $1,000 to rent a place for his next craps game. To help finance the game, Detroit bets Sky Masterson, played by Marlon Brando, that he cannot make missionary Sarah Brown, portrayed by Jean Simmons, go on a date with him.

Another musical hit for Sinatra, Guys and Dolls was the fifth highest-grossing film of the year in the United States. Guys and Dolls received four Oscar nominations and decades later, the film placed 23rd on the American Film Institute's list of the greatest musicals. Guys and Dolls' signature song, "Luck Be a Lady," became one of Sinatra's most popular hits in the 1960s. Ironically enough though, Brando sings the song in the film.

5 Sinatra Stuns As One Of The Most Menacing Villains Of The 1950s In Suddenly (1954)

• IMDb Rating: 6.8

Perhaps the most underrated movie in Sinatra's filmography Suddenly is a film noir in which, for the first time in his career, Sinatra played a villain. Fresh off an Oscar win for From Here to Eternity, Sinatra displayed his range as an actor playing John Baron, a killer who holds a family hostage as he awaits his chance to assassinate the President of the United States.

Sinatra gives a brilliant, against-type performance in Suddenly, one that earned him some of the best reviews of his career. Prominent film critic Bosley Crowther hailed Sinatra's performance as a melodramatic tour de force. Newsweek was also highly complimentary of Sinatra's performance, calling his character John Baron one of the most repellent killers in American screen history. One reason why Suddenly remains a lesser-known Sinatra work is because, after John F. Kennedy's death, Sinatra withdrew the film from circulation. According to legend, Lee Harvey Oswald watched Suddenly days before assassinating Kennedy.

4 Sinatra Became An Oscar Winner For From Here To Eternity (1953)

• IMDb Rating: 7.6

During the 1940s, Sinatra was one of the biggest names in entertainment, finding monumental success in both music and film. However, the early 1950s saw a career slump for Sinatra, who struggled with declining record sales and a high-profile divorce. However, Sinatra's fortunes changed when he was cast in Fred Zinnemann's From Here to Eternity. The film tells the story of three soldiers stationed in Hawaii in the months leading up to the attack on Pearl Harbor.

Sinatra, in the supporting role of Private Angelo Maggio, received rave reviews for his performance. From Here to Eternity won eight Academy Awards, including an Oscar for Best Supporting Actor for Sinatra. The New York Post called Sinatra's performance immensely touching, while John McCarten of The New Yorker articulated how From Here to Eternity elevated Sinatra to first-rate actor status. In 2002, the Library of Congress selected From Here to Eternity for preservation in the National Film Registry.

3 Some Came Running Was The First Collaboration Between Sinatra And Dean Martin (1958)

• IMDb Rating: 7.2

Real-life friends Sinatra and Dean Martin first appeared on-screen together in Vincente Minnelli's Some Came Running. Eventually, the two would collaborate on eight films. In Some Came Running, Sinatra plays Dave Hirsh, a bitter military veteran and former writer who returns to his hometown where he faces family secrets and romantic entanglements.

One of the most successful films of Minnelli's career, Some Came Running was one of the year's ten highest-grossing films. At the 31st Academy Awards, Some Came Running received five nominations, however, the Academy snubbed Sinatra of the Best Actor nomination. Critics lauded Sinatra's performance, with Variety writing, "Sinatra gives a top performance, sardonic and compassionate, full of touches both instinctive and technical." Sinatra did manage to win the Laurel Award for Top Male Dramatic Performance.

2 The Manchurian Candidate Is An All-Time Great Political Thriller (1962)

• IMDb Rating: 7.9

Directed by John Frankenheimer, The Manchurian Candidate is one of cinema's greatest political thrillers. Made during the height of the Cold War, The Manchurian Candidate's plot revolves around an American POW from the Korean War who becomes brainwashed as an assassin by an international Communist conspiracy. In the film, Sinatra plays Major Bennett Marco, the central figure who tries to uncover the conspiracy.

A film that has aged like fine wine, The Manchurian Candidate is an older film that feels wholeheartedly modern. Roger Ebert stated the film does not play like a "classic," but rather it remains as alive and smart as when it first premiered. The National Film Registry inducted The Manchurian Candidate in 1994 for its invaluable importance in capturing the paranoia of the Cold War. For his role as Major Marco, Sinatra earned a nomination for Top Action Performance from the Laurel Awards.

1 The Man With The Golden Arm Is Sinatra's Greatest Film Acting Performance (1955)

• IMDb Rating: 7.3

In 1955, Sinatra gave the best performance in his career in Otto Preminger's The Man with the Golden Arm. Sinatra stars as Frankie Machine, a skilled card dealer who struggles with heroin addiction. One of the most controversial films of Hollywood's Golden Era, The Man with the Golden Arm was one of the first major Hollywood productions under the Production Code to openly address drug addiction.

Sinatra lobbied hard to land the lead role in The Man with the Golden Arm, with Marlon Brando also in contention for the part. Once he won the role, Sinatra spent time in drug rehabilitation clinics, observing addicts attempting to quit cold turkey. He also learned how to play the drums. For his groundbreaking performance, Sinatra earned nominations from the Academy Awards and the BAFTAs for Best Actor while winning Top Male Dramatic Performance at the Laurel Awards. In 2020, the Library of Congress voted The Man with the Golden Arm into the National Film Registry.