Season 2, Episode 31 The Raffle Ticket

Denny buys a chance on a trailer, sells shares in it---and wins! Denny: Michael O'Shea. Steve: William Bishop. Earl: James Dunn. Amy: Frances Bavier. Myra: Angie Dickinson. Mabel: Isabelle Dwan. Milkman: George Chandler. Sewerman: Frank Sully. Mailman: Parley Baer.

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Chris Geere and Aya Cash
The You're the Worst cast can act, but can they draw? (Nope!)

We challenged Chris Geere, Aya Cash, Kether Donohue and Desmin Borges to draw 45-second portraits of each other and the results were... interesting