He was part of a popular vaudeville duo with Neely Edwards.
[2] The comedy team starred together on screen in a series of Hallroom Boys Comedies, adapted from the comic strip,[5][6] and again for National Film Corporation in "Flanagan and Edwards" shorts.
Their son Edward Flanagan, also became an actor, known in film as Dennis O'Keefe.
[7] Flanagan was performing at the Metropolitan Theatre on August 13, 1925, and was taken ill and rushed to Hollywood Hospital.
He had an operation for stomach ulcers and developed peritonitis and died on August 18, 1925.