She began performing at a young age and was featured on a radio program in North Dakota, where she grew up.

In New York City during the 1940s, she played with jazz musicians such as Dizzy Gillespie, Billie Holiday, Art Tatum, Coleman Hawkins, and Thelonious Monk.

Her family was musically inclined; her mother played guitar and her father, in addition to constructing violins, allowed his barbershop to be the meeting place for the town's musicians.

[2] At the age of fifteen, Osborne joined a trio led by pianist Winifred McDonnell, for which she played guitar, double bass, and sang.

During this time, she heard Charlie Christian play electric guitar in Al Trent's band at a stop in Bismarck.

In 1945, Osborne headlined a performance with Dizzy Gillespie, Art Tatum, Coleman Hawkins, and Thelonious Monk in Philadelphia, to reviews and audiences that praised her specifically.

There she recorded with Mary Lou Williams in 1945, Coleman Hawkins, Mercer Ellington, and Beryl Booker in 1946, and led her own swing trio.

Her trio lasted from 1945 to 1948 and played in clubs on 52nd street, had a year-long engagement at Kelly's Stables, and made several recordings.

In 1991, in what would be her final performances, Osborne returned to the Village Vanguard in New York for a week-long engagement.