He worked as a golf caddy and shoe salesman before he got his first good break, playing in a show on a South American cruise ship in 1934.

[3] In 1940, he was signed by Metro-Goldwyn-Mayer to make films and, although his past career had been in musicals, he was initially cast in the drama Susan and God (1940).

He appeared in a musical comedy in Hullabaloo (1940), then had a small role in the drama Keeping Company (1941) and was the juvenile in The Wild Man of Borneo (1941).

Dailey was loaned out to 20th Century Fox for Moon Over Her Shoulder (1941), then appeared opposite Donna Reed in Mokey (1942).

Their association began brilliantly with Mother Wore Tights (1947) in which Dailey supported the studio's biggest star, Betty Grable.

[citation needed] Fox tried Dailey in a comedy, Chicken Every Sunday (1949) with Celeste Holm, then he teamed with Anne Baxter in the popular musical You're My Everything (1949).

The other songs, "Take Me Out to the Ball Game" and "In the Good Old Summer Time", capitalized on the success of two MGM blockbuster films of the same names, starring Gene Kelly, Esther Williams, and Frank Sinatra (Take Me Out to the Ball Game); and Judy Garland and Van Johnson (In the Good Old Summertime).

[7] Dailey starred in a film for John Ford, When Willie Comes Marching Home (1950) which was a mild success at the box office.

Dailey was reunited with Anne Baxter in A Ticket to Tomahawk (1950), often noted as one of the first screen appearances of Marilyn Monroe,[citation needed] who played a dance hall girl.

[8] Dailey was scheduled to appear in the 20th Century Fox musical extravaganza There's No Business Like Show Business (1954), which featured Irving Berlin's music and also starred Monroe, Ethel Merman, Mitzi Gaynor, Johnnie Ray, and Donald O'Connor, whose wife Gwen divorced him and married Dailey around that time.

[9] Dailey went to Metro-Goldwyn-Mayer to play GI-turned-advertising man Doug Hallerton in It's Always Fair Weather (1955) alongside Gene Kelly.

[10] Dailey returned to Fox for one more musical, The Best Things in Life Are Free (1956) to play songwriter Ray Henderson opposite Gordon MacRae.

As the musical genre began to wane in the late-1950s, he moved on to various comedic and dramatic roles on television, including starring in The Four Just Men (1959–1960).

He starred with Cantinflas in Pepe (1960), had a cameo in Hemingway's Adventures of a Young Man (1961), and made Four Nights of the Full Moon (1963) in Spain.

In the late 1960s, Dailey toured as Oscar Madison in a road production of The Odd Couple, co-starring Elliott Reid as Felix Unger and also featuring Peter Boyle as Murray the cop.

[1] Films: Radio: Television: Stage: Other: For a number of years, movie exhibitors voted Dailey among the most popular stars in the country: