Complex sentence: In the 1960s, Belletto worked at the New Orleans Playboy Club fronting the house band and serving as Musical/Entertainment Director, booking nationally-known acts into the venue.
Split into simpler sentences: In the 1960s, Belletto wore two "hats" at the New Orleans Playboy Club; fronting the house band, as well as Musical/Entertainment Director. As Entertainment Director, one of his responsibilities was to book nationally-known acts into the venue.