From Homestar Runner Wiki
Gambling has been seen on a couple of occasions in Free Country, USA. Usually, something other than money is at stake, such as spending the night at The King of Town's castle (the bet), changing one's name to "Kevin DuBrow" (also in the bet), or a car (pop-up).
Strong Bad once played cards with Homestar and lost. To uphold his end of the bet, he was forced to wish everyone a happy Mother's Day. Although he vowed never to play cards again, he later did so in the email pom pom's Easter egg, in which he played cards with Bubs and won the game by beating Bubs' Monkeydude with two Abdis and a Viklas. In the same email, he also sings an intro song about gambling ("Oh, I'm an email gambler. That means I play cards with emails. Full house.").
- A Mother's Day Message — Strong Bad loses a bet.
- Email 1 step ahead — Strong Bad's opening line goes, "This one better be good, man. I got a lotta money riding on this one."
- Email the bet — Homestar and Strong Bad make a bet about Homestar being cool.
- Email pom pom — The email intro song and Easter egg both refer to playing cards with, or gambling with, emails.
- Senorial Day — Senor Cardgage says, "Gamble around the campfire, children." (Although it's possible Senor Cardgage also used the word "gambol", meaning "to skip about".)
- Email pop-up (Easter egg) — The Cheat won a car after beating Bubs in dominos.
- Email licensed — Strong Bad mentions going to the dog tracks.
- Place ya bets! — The Deleteheads place wagers on what will happen in the upcoming 200th email.
- 4 Gregs — The Mascot states "AT LEAST TRY TO BEAT THE SPREAD" in his cheer.
- Dangeresque 3: The Criminal Projective — Dangeresque plays Rock, Paper, Baccarat against Perducci to get his secret plans.
- Poker Night at the Inventory — Strong Bad plays poker with characters from other games.