Tipton gained an interest in jazz while in high school, playing the piano and saxophone. At the age of 19, Tipton obtained documents listing him as a man, bound his breasts, padded his pants and embarked on a serious music career as a male jazz pianist. Initially he presented himself as a man only when he performed but by 1940 he was living as a man in his private life too. His deception lasted for fifty years through five common-law wives, children and a busy touring and recording schedule.
In 1936, Tipton was the leader of a band playing for a local radio station. Two years later he began touring the Midwest playing at taverns and dances, finally landing a 2 1/2 year long gig at Joplin, Missouri's Cotton Club playing with George Meyer's band. He toured the Pacific Northwest with Meyer in 1949 and eventually landed jobs backing the Ink Spots, The Delta Rhythm Boys and Billy Eckstine. He formed his own trio and landed his first recording contract when he was spotted by a talent scout while playing in Santa Barbara, California. The trio recorded two successful albums of jazz standards for Tops Records in 1957.
After the albums' success, Tipton's trio was offered a position as the house band at the Holiday Hotel in Reno, Nevada and received an invitation from Tops to record four more albums. Tipton turned down both offers, possibly to avoid being exposed as a woman as the publicity heated up. Instead he moved to Spokane, Washington where the trio worked as the house band at Tin Pan Alley and Tipton began working as a talent broker. By 1970 Tipton retired from music due to arthritis.
Tipton's personal life seemed to dictate many of his life choices. All but the first of his five common-law wives believed he was a man. He told them all that he was in a car accident that damaged his ribs and genitals which required having to bind his chest at all times. His three sons were all adopted and believed him to be a man too, until the day the paramedics were called in as he was dying and the truth was exposed when the bindings were necessarily cut. Tipton was a very talented musician but he avoided the limelight in order to live life his way and as a result, never gained the appreciation he deserved as a musician.
