The Way the Cookie Crumbles
Cleveland and his friends target a con man who scammed Cookie and Freight Train out of their life savings; Rallo uses a toy microphone to give his vocal skills a workout.
To Live and Die in VA
Lester grows suicidal after losing his life savings in Cleveland's beer truck business; Rallo opens his own barbershop.
Cleveland befriends celebrity idol Barry Shadwell and joins his sailing team, but has a change of heart about participating in a sailing event after he and Shadwell share a kiss.
Back to Cool
After Junior bonds with Donna's ex-husband, Robert, Cleveland challenges Robert to a "Coolympics" competition.