Osie worked with Clark Terry in the Navy band 1944-45 and then freelanced around Chicago until hooking up with Earl Hines. He could be heard playing at Minton's Playhouse with Tony Scott, or backing Dorthy Donegan, and toured Europe with Illinois Jacquet, all in the 1950s. Mostly he was a session musicians in the New York television and recording studios. His arrangements included a hit by singer Dinah Washington, 'Fool That I Am,' and can be heard on his own dates.