In addition to Tommy Dorsey (1939–1942, 1945, 1954–1955), where Rich met and performed with Frank Sinatra, Rich also played with Benny Carter (1942), Harry James (1953-1956–1962, 1964, 1965), Les Brown, Charlie Ventura, and Jazz at the Philharmonic, as well as leading his own band and performing with all-star groups. In October 1944, at the Paramount Theater Rich mentioned to Sinatra that he was interested in starting his own band. Sinatra wrote him a check for $40,000 and said "Good Luck. This'll get you started."[citation needed]

For most of the period from 1966 until his death, he led a successful big band in an era when the popularity of big bands had waned from their 1930s and 40s peak. Rich also served as the session drummer for many recordings, where his playing was often much more understated than in his own big-band performances. Especially notable were Rich's sessions for the late-career comeback recordings of Ella Fitzgerald and Louis Armstrong, on which he w