Bob and Margaret: The Player (2001)

Run Time - 30 min.  |  
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When Margaret and the women at the clinic work press Bob into service helping out for the Women's International Innersole Fund benefit concert, Bob discovers Internet day trading. As Margaret desperately searches for a way to pay for a well-known act for the concert, Bob becomes increasingly obsessed with his stocks, taking his initial successes as a sign to invest more. When his investments tank, he covers his shame by taking Margaret out for a nice dinner -- and spontaneously writing a check to pay for a celebrity guest.