If there's a male playwright who understands what it's like for women to live and love in a shallow culture, it's Neil LaBute. His 1997 film In the Company of Men is a blistering portrait of misogyny, and his play Fat Pig examines fat phobia in a way that left me speechless (but later gave me days' worth of issues to talk about). His latest play, reasons to be pretty, is now playing on Broadway.
The plot revolves around Greg and Steph, a couple whose relationship implodes after Steph finds out that Greg described her as having a "regular" face. After the split, Greg attempts to understand how our views of physical beauty shape our self-esteem, our relationships, and our experiences. The play is earning positive reviews, so if you're into examining the beauty ideal while taking in some thee-ay-tuh, snap up tickets.
To see a (vaguely NSFW) promotional video featuring regular Janes and Joes talking about their body image,