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When Hairy Met Sadly: The Landmark Romcom’s Best and Worst Men’s Haircuts

It’s about time we discuss what the hell was up with Billy Crystal’s hair.

Eve Peyser
8 min readJan 27, 2022
Harry likely contemplating what the fuck is going on with his hair.

When Harry Met Sally is considered the best romantic comedy of all time, and it’s easy to see why. Nora Ephron’s dialogue is funny! Meg Ryan’s performance is so charming! Carrie Fisher is fuckin’ hilarious! Billy Crystal, who I usually find unbearable, is exceedingly bearable! But When Harry Met Sally is a movie that largely takes place in the 1980s, and because of that, almost everyone dresses and looks like dogshit.

The worst aesthetics of the era are most clearly manifested in the haircut Billy Crystal sports throughout the movie, which is also the haircut he had in real life at the time. The haircuts of the other main characters are not much better, but there are a few winners.

Hair is not only the texture on our head, but that of our lives, which the characters in When Harry Met Sally demonstrate. While the movie has been analyzed to death, not nearly enough attention has been given to the follicles that sprout from the scalps of Harry, his best friend Jess, and the other men of the film. Thank god I’m here to tell you what’s what.

13. Pictionary Party Guest

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Eve Peyser
Eve Peyser

Written by Eve Peyser

nyc native living in the pnw. read my writing in the new york times, nymag, vice, and more.

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