The biggest laugh was when thy would announce the winners, and would have one of their artists do a two page spread of the Playboy All Star Band. Typically, it would go something like this:
Trumpets - Miles Davis, Al Hirt, Dizzy Gillespie, Herb Alpert
Trombones - J. J. Johnson, Kai Winding, Bob Brookmeyer
Saxes - Cannonball Adderley, Paul Desmond (alto), John Coltrane, Stan Getz (tenor, Gerry Mulligan (bari)
Rhythm Section - Dave Brubeck (piano), Charlie Byrd (guitar), Charles Mingus (bass), Buddy Rich (drums), Lionel Hampton (vibes)
Vocalists - Frank Sinatra (male), Barbra Streisand (female), Beatles (group)