Boardwalk Baron is a parody of Monopoly that appears in Hot Mess.
During the events, Frank Heffley and the rest of the family was excited to play but Susan Heffley refused to let the family play it because it 'teaches people to be greedy'.
During the game, Manny Heffley bought several properties, all with hotels. He had so many properties at one point if someone landed on one of his properties, they will go bankrupt. So he made people pay lots of money to safely pass. Many people turned themselves into jail so they would not hit one of Manny's properties.
Frank did not want to go bankrupt first so he tried to give Manny a new bicycle for his next birthday if Frank could safely pass, but Manny refused. Frank landed on one with no cash, causing him to lose the game. As punishment, he was forced to sing on the Boardwalk near the beach until 20 Dollars were deposited in his hat.
After Frank lost the game, the family began thinking of ways to punish the second place loser, but they were interrupted by Susan, who slid the game into the trash.