Complex sentence: Over the years in the 1950's and 1960's he worked in clubs in New York, Chicago and Boston and played with musicians such as Bobby Hackett, Jimmy McPartland, Doc Cheatham, Vic Dickenson, PeeWee Russell, and Wingy Manone.
Split into simpler sentences: Over the years in the 1950's and 1960's he worked in clubs in New York, Chicago and Boston. In those years he played with musicians such as Bobby Hackett, Jimmy McPartland, Doc Cheatham, Vic Dickenson, PeeWee Russell, and Wingy Manone.