He's putting that to the test with "Sam's Game," debuting Thursday on Playboy TV and filmed at The Palms casino and resort in Las Vegas.
Inspired by poker nights that Simon regularly hosted for friends, the show includes Dave Attell, Artie Lange, Norm MacDonald and Jeff Ross; Jennifer Tilly, who's Simon's former wife; and Brande Roderick, 2001 Playmate of the Year and a "Celebrity Apprentice" contestant.
"The stakes aren't the biggest, the players aren't the best, but the game is definitely the funniest," Simon said.
Others joining in the Texas Hold 'Em games include professional poker champions Jennifer Leigh and Phil Laak.
The idea for the show came from Playboy TV, which had heard about his "raucous and very entertaining" private games, said Simon, former producer for "The Simpsons."
"I've spent years in development to try to get shows on the air. When a network calls and says, `We want to shoot this,'" Simon said, the answer is yes.
The show's self-described "raunchy" comedy and language are unfiltered.