Realized that websites like this would be PERFECT for making custom Poker Nights using the Inventory as a setting. Consider this my take, using characters I've seen as part of good fan rosters as well as my own picks for who I thought would be funny. :)
Characters:
Manuel "Manny" Calavera (Grim Fandango)
Murdoc (Gorillaz)
Ellis (L4D2)
Charlie (Smiling Friends)
Dealer - AM (IHNMAIMS)
Character descriptions are mostly ripped from wiki pages, and there's likely a few kinks that still need to be buffed out with message ratings. But I think it's a good time regardless.