- Started his entertainment career as a dancer in vaudeville shows, which led to roles in the 1930s Broadway shows Life Begins at 8:40 and On Your Toes.
- Signed a contract with MGM in 1936 and made his feature debut in the 1936 biopic The Great Ziegfeld.
- Was originally cast as the Tin Man in The Wizard of Oz (1939), while Buddy Ebsen had landed the role of the Scarecrow. Eventually, Bolger was able to talk his way into switching roles, a fateful move for Ebsen, who had to drop out of the film due to an allergic reaction to the Tin Man makeup.
- Spent most of the 1940s performing on Broadway and in a WWII USO Tour. In 1949, he won a Tony Award for his lead role in the Broadway production of Where's Charley?
- Starred in the ill-fated sitcom Where's Raymond? (also known as The Ray Bolger Show) from 1953 to 1955.
- Appeared in a variety of guest spots on such shows as The Partridge Family, The Love Boat, and Baretta near the end of his career.
- Was the last surviving marquee cast member from The Wizard of Oz until his death in 1987 from cancer.
- Actor John Bolger is his great-nephew.
- 1962, Tony — Actor (Musical): Nominee
- 1976, Emmy — Outstanding Single Performance by a Supporting Actor in Comedy or Drama Special: Nominee
- 1949, Tony — Actor (Musical): Winner
- Gwendolyn Rickard — Wife
- James Bolger — Father
- Anne Bolger — Mother
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