He played "Dragline" in Cool Hand Luke (1967), winning the Academy Award for Best Supporting Actor for the role and being nominated for the corresponding Golden Globe.

Among other films in which he had a significant role are Lonely Are the Brave, Charade, Strait-Jacket, McHale's Navy, Hush… Hush, Sweet Charlotte, Mirage, Shenandoah, The Sons of Katie Elder, The Flight of the Phoenix, In Harm's Way, The Dirty Dozen, The Boston Strangler, Guns of the Magnificent Seven, tick… tick… tick…, Cahill U.S.

Kennedy is the only actor to appear in all four films in the Airport series, reprising the role of Joe Patroni three times.

[citation needed] Kennedy graduated in 1943 from Chaminade High School in Mineola, Long Island, New York.

Kennedy served in the infantry under George S. Patton, fought in the Battle of the Bulge, and earned two Bronze Stars.

He appeared in several Hollywood movies, including as a sadistic jail guard in the Kirk Douglas modern Western Lonely Are the Brave (1962), a ruthless criminal in the Cary Grant suspense film Charade (1963) and in the Joan Crawford thriller Strait-Jacket (1964).

In 1970, he appeared in the disaster film Airport, in which he plays one of its main characters, airline troubleshooter Joe Patroni.

[5] Kennedy co-starred with Clint Eastwood in Thunderbolt and Lightfoot and The Eiger Sanction, and with ensemble casts in the disaster film Earthquake and the Agatha Christie mystery Death on the Nile.

Kennedy starred in two Japanese productions, Junya Satō's Proof of the Man in 1977 and Kinji Fukasaku's Virus in 1980.

Although Proof of the Man was only released theatrically in Japan and Virus saw a financially unsuccessful truncated cut in the U.S., Kennedy was highly enthusiastic about his involvement.

He played Captain Ed Hocken in all three entries of The Naked Gun film trilogy (1988, 1991, 1994) alongside Leslie Nielsen, Priscilla Presley and O. J. Simpson.

Kennedy made his final film appearance in The Gambler (2014) as Ed, the dying grandfather of Mark Wahlberg's Jim Bennett.

His role lasts for less than two minutes during the film's opening scene, wherein Ed (moments before his death) bequeaths the responsibilities of patriarch to a heartbroken Jim.

[14] Following his experiences working for the Far East Network during WWII and professional involvement with Proof of the Man and Virus, Kennedy maintained a lifelong affinity for Japan and its culture.