Stereotypical Portrayals

Showgirls (1995)
Coyote Ugly (2000)
Fast Times at Ridgemont High (Heckerling 1982) - Although a striking directoral debut, Heckerling fails to break away from "the male gaze" that has dominated -- and today still dominates -- the majority of films, particularly how women are not only represented but how they're filmed, compared to men.
Almost Famous (Crowe 2000) - Rebuffed woman nearly overdoses. Hmm, good thing there's (almost) always the nice guy who loves her to come to the rescue. Also, the women (Band Aids) are regarded as trophies and end up sold to other rock bands during poker games.
Catch Me If You Can (Spielberg 2002)
American Beauty (Mendes 1999) - Middle-aged man lusts after young, beautiful girl. How many times has that scenario been played out? (Thank heavens it's only a subplot!)
Pretty Woman (Marshall 1991)
Woodstock (Wadleigh 1970) - Stoned, nude hippies romp in the mud. Wasn't Woodstock supposed to be a rock festival? Where's the music???
Pennies From Heaven (Ross 1981) - Critics and audiences were expecting "The Jerk 2" and instead got Christopher Walken dancing down to his boxers. (And they were disappointed? Go figure!) However, because of the film's setting, gender roles were not lax, and the unmarried schoolteacher's pregnancy and subsequent abortion denounced her as a whore in society.
How to Make an American Quilt (1995) - While preparing for marriage, a young woman learns of her female relatives' pasts, one of whom denied her daughter the opportunity to attend college because she -- as dictated by the society at the time -- felt it more important for her son to have that opportunity.
Striptease (1996) - Demi Moore takes it all off (well, above the waist) while her daughter watches; the "Mommy, you looked beautiful" line was slightly unsettling.