When Midge and Lenny meet up at the bar, before going to the filming of Miami After Dark, a fan walks up to Lenny, calling him "Mr Bruce." Lenny responses by telling the fan that, "Mr Bruce was my mother." Amy Sherman-Palladino (creator/producer/director of the show) knew Sally Marr, who was the real Lenny Bruce's mother and whenever anyone learned who she was, she'd call herself "Mr Bruce", so the line's in reference to this.
The "Miami After Dark," show with the pipe smoking, preppy host Brye Adler, is a play on Playboy After Dark (1969), hosted by Hugh Hefner. However Lenny Bruce was never on "Playboy After Dark", he was on an earlier, less known show hosted by Hugh Hefner called Playboy's Penthouse (1959).
The episode won 3 Emmy Awards for Outstanding Period and/or Character Makeup (Non-Prosthetic), Outstanding Cinematography for a Single-Camera Series (One Hour) and Outstanding Music Supervision.
The episode of the game show, "To Tell the Truth" that Zelda and Shirley are watching aired on 11/21/60 and featured Judy Delp, the 1960 national baton twirling champion.