He is best known for his roles in The Wizard of Oz (1939) as the Scarecrow and in Walt Disney's holiday musical fantasy Babes in Toyland in 1961 as the villainous Barnaby.

He began his career in a vaudeville tap show, creating the act "Sanford & Bolger" with his dance partner.

[8] In 1932 he was elected to the theater club The Lambs[9] and performed on opening night at Radio City Music Hall in December 1932.

[10] After starring in Richard Rodgers' first stage production of On Your Toes in 1936, in which he played the male lead Junior, as well as the hero of the Slaughter on Tenth Avenue ballet within the musical, Bolger signed his first cinema contract with MGM in 1936, and although The Wizard of Oz was early in his film career, he appeared in other movies of note.

[12] Bolger toured in USO shows in the Pacific Theater during World War II,[13][14] and appeared in the United Artists wartime film Stage Door Canteen (1943).

(1948), for which he won the Tony Award for Best Performance by a Leading Actor in a Musical and in which he introduced "Once in Love with Amy", the song often connected with him.

He continued to star in several films, including Walt Disney's remake of Babes in Toyland (1961) and smaller cameos throughout the 1960s and 1970.

In his later years, he danced in a Dr Pepper television commercial, and in 1985, he and Liza Minnelli, the daughter of his Oz costar Judy Garland, starred in That's Dancing!, a film written by Jack Haley Jr., the son of Jack Haley, who portrayed the Tin Woodman in The Wizard of Oz.

[19] In 2016, the City of Boston commissioned a mural in Ray Bolger's honor in the Codman Square section of the Dorchester neighborhood.

[24] He was the only one of Judy Garland's Oz costars who attended her funeral, joining Harold Arlen, the composer of "Over the Rainbow", and his wife, Anya Taranda.

"[26] Bolger's Scarecrow is ranked among the "most beloved movie characters of all time" by AMC and the American Film Institute.

[27][28] For his contributions to the film industry, Bolger received a motion pictures star on the Hollywood Walk of Fame in 1960.