He appeared in four Broadway plays, as Howard Haines in Last Stop (1944), playing an unknown man in The Bat (1953), A.J. Alexander in Sing Till Tomorrow (1953), and Captain Randolph Southard in The Caine Mutiny Court-Martial (1954–1955), which starred Henry Fonda.
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Two years before he was cast as Milburn Drysdale, a greedy bank president, on the hit TV sitcom The Beverly Hillbillies, Bailey appeared on the CBS sitcom My Sister Eileen with Shirley Bonne, Elaine Stritch, Jack Weston, Rose Marie, and Stubby Kaye.
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He reportedly began suffering symptoms of Alzheimer's disease, which visibly affected his performance in the last episodes of The Beverly Hillbillies, and he was completely unable to work after 1975.
Raymond Chandler | Everybody Loves Raymond | Raymond Carver | Bill Bailey | Ringling Bros. and Barnum & Bailey Circus | Pearl Bailey | Kay Bailey Hutchison | Derek Bailey (guitarist) | Derek Bailey | Old Bailey | Raymond Queneau | Raymond Dart | Rumpole of the Bailey | Eric S. Raymond | Raymond Briggs | David Bailey | Raymond Pettibon | Raymond | Bailey | Raymond Poincaré | Raymond Massey | Raymond Loewy | Raymond Kelly | Raymond James Stadium | Raymond van Barneveld | Raymond E. Feist | Raymond Burr | Raymond Benson | Gene Raymond | F. Lee Bailey |
In the 1960–1961 season, Rose Marie co-starred with Shirley Bonne, Elaine Stritch, Jack Weston, Raymond Bailey, and Stubby Kaye in the CBS sitcom My Sister Eileen.