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- Brad Pitt as Jerry Welbach
- Julia Roberts as Samantha Barzel
- James Gandolfini as Winston Baldry
- J.K. Simmons as Ted Slocum
- Bob Balaban as Bernie Nayman
- Sherman Augustus as Well Dressed Black Man
- Michael Cerveris as Frank
- David Krumholtz as Beck
- Gene Hackman as Arnold Margolese