In February 1986, the late John Hughes released Pretty in Pink with Molly Ringwald, Jon Cryer (who turns 50 today!), Andrew McCarthy and James Spader — and we've been in love with the classic film ever since!
Click through the gallery above to see the cast then and now.
After losing best friend Andie to Blane, things weren't so Duckie for Jon, 51, either. His sitcoms The Famous Teddy Z, Partners and The Trouble With Normal each got canceled after just one season. Of course, his next was Two and a Half Men, which wrapped after 12 seasons in February 2015!
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