Tootsie
One of the touchstone movies of the 1980s, Tootsie stars Dustin Hoffman as an out-of-work actor who disguises himself as a dowdy, middle-aged woman to get a part on a hit soap opera. The scheme works, but while he/she keeps up the charade, Hoffman's character comes to see life through the eyes of the opposite sex. The script by Larry Gelbart (with Murray Schisgal) is a winner, and director Sydney Pollack brings taut proficiency to the comedy and sensitivity to the relationship nuances that emerge from Hoffman's drag act.