Mary Santora is an alcoholic and compulsive gambler who does stand up. She has made a career out of turning a difficult life into entertainment as a stand up comedian and cohost of Cleveland's Alan Cox Show. Now, she is risking a relationship with her boyfriend and her career to move to New York City to double down on her comedy. Tom asks "is this the beginning of a dream come true or a disaster waiting to happen."

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Website: MarySantora.com