Friends
The One With the Hypnosis Tape
S3 E18:
Phoebe is distraught when her brother wants to marry a woman twice his age. While working as a waitress, Monica gets a tip from an admirer worth a small fortune. A hypnosis tape makes Chandler act like a woman.
Starring
Jon Favreau, Giovanni Ribisi, Debra Jo Rupp
Director
Robby Benson