Movies With An Older Woman-Younger Man Romance

In Amy Schumer's "Last Fuckable Day" sketch, Sally Field is a punch line. She's the go-to example of how Hollywood marginalizes women of a certain age. Whereas male movie stars are consistently paired with love interests 10 or 20 years their junior (see: who's been cast opposite Tom Cruise in the new Mummy movie), Field was relegated to playing Mrs. Gump at the age of 47. Tom Hanks is merely 10 years younger than she is. Men get increasingly younger romantic partners; women have to play mothers.
But in the new movie Hello, My Name Is Doris, Field pursues a man more than three decades her junior. Field plays Doris, who finds herself smitten with John Fremont (Max Greenfield), the new guy in her office. Bereft by the recent loss of her mother, for whom she cared her entire life, Doris passionately attempts to figure out how she could possibly win John. It turns out her zany wardrobe is a hit in Williamsburg, and the two end up becoming friends.
Doris may be a bit clueless, but the movie doesn't deny Field her sexuality. At one point, hipsters at a concert assume that John is sleeping with her. Sure, Doris is sort of dotty, and she certainly has no idea how to seduce a man, but she's still seen as desirable.
The history of movies featuring romantic and/or sexual relationships between older women and younger men is a fraught one. Yes, Mrs. Robinson is hot in The Graduate, but she's also portrayed as a boy-crazy lady who ruins lives. Cinematic women who engage in affairs with younger men are often sexy, but also broken in some way or another. Though the woman has the upper hand in terms of age, she is often a conquest for the virile dude.
Hello, My Name Is Doris, out March 11, doesn't exactly engage with those tropes. We won't spoil whether or not Doris and John end up together, but ahead we look at some other movies featuring the age gap you're not used to seeing.