Major Awards Over the years Shep received many awards, nominations and tributes for his work
Playboy's Annual Writing Awards
Humor Satire Award - 2nd Place
"Ollie Hopnoodle's Haven of Bliss"
Given for his short story: "Ollie Hopnoodle's Haven of Bliss"
On his series of 7 Shepherd's pie tapes he mentions that the following stories were winners of the Playboy Humor Award: Ollie Hopnoodle's Haven of Bliss - 7/68; Leopold Doppler and the Orpheum Gravy Boat Riot - 10/65; County Fair - 9/69; Skut Farkas and the Murderous Mariah - 4/67
I have confirmed with copies of Playboy the following winners: Wanda Hickey's Night of Golden Memories - 6/69; Ollie Hopnoodle's Haven of Bliss -7/68 (2nd Place); Return of the Smiling Wimpy Doll - 12/67, and Leopold Doppler and the Orpheum Gravy Boat Riot - 10/65
The awards section did not mention County Fair which would have been the same year as Wanda Hickey, nor did it mention Skut Farkas which was the same year as Smiling Wimpy.
Shep also sent the letter below to Playboy thanking them for an award given to "The Mole People..."