Billie's stay at the Down Beat was so successful due to Tucker's playing that she decided to keep him as her accompanist.

The partnership lasted until 1949, where Tucker quit due to Holiday's abusive lover, John Levy, threatening him.

After leaving Holiday in 1949, Bobby Tucker began playing for Billy Eckstine.

Not much is known about this partnership, but there is a 1960 album, No Cover, No Minimum which features Tucker playing piano for Eckstine.

In 1973 Tucker played for Billy Eckstine at the Hobart (Tasmania, Australia) Wrest Point Casino.