Punday at Callahan's is a weekly tradition every Tuesday where the patrons go around a circle making puns on a specific topic. Punsters are eliminated when they can not think of an appropriate pun and the last man standing gets their bar tab for the night refunded.

Doc Webster tends to dominate the Punday Night competitions, with Long Drink McGonnigle not far behind. However, some of the other regulars, such as Jake, can become dark horse contenders if they pick the right moment and the right quip.

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