The show was designed as a way to spread Playboy magazine's influence beyond the printed page and to help non-readers get to know Hefner.

[2] The show, initially recorded at ABC's Chicago station WBKB, was set up as if it were a party at Hefner's own apartment, with many Playboy Playmates and bunnies in attendance.

[3] After the second season's planned programs were completed, Sammy Davis Jr. was booked to play a Chicago nightclub and expressed a desire to appear on the show.

Hefner was unable to book additional production time at the WBKB Studios on State Street, but was able to strike a deal with CBS's WBBM-TV to reconstruct the Playboy's Penthouse set at their McClurg Court studios and tape an additional five programs there in November and December 1960, the Davis guest appearance being the first segment taped.

In 1969, Hefner launched a show in a very similar style, Playboy After Dark which was taped in Los Angeles.