Pretty In Pink - 1986
Molly Ringwald plays Andie, a high school outcast who is either hanging out with her boss or her quirky classmate Ducky (who has a secret crush on her.) One of the popular boys at school asks Andie out, but things get complicated as the two are from totally different social worlds. This John Hughes classic stands tall with The Breakfast Club and Sixteen Candles.
17 Again - 2009
Matthew Perry plays a former basketball player who threw away his future in the sport to marry his girlfriend and raise their child. 20 years later, he finds himself divorced and alone. He somehow transforms back into his teenage self (Zac Efron) for a chance of redemption, but he doesn't realize that he might be jeopardizing his future.