10 items
A witty modernization of Shakespeare's The Taming of the Shrew transplanted to a Seattle-area high school, starring Julia Stiles and Heath Ledger. A modest hit in theaters, it grew into a generational classic and launched the breakout careers of its three young leads.
A 13-year-old wishes herself "thirty and flirty and thriving" in 1987 and wakes up in 2004 as a magazine editor with no memory of the years between. Jennifer Garner's charm — and one glorious "Thriller" dance — turned it into a millennial comfort classic.
A romantic comedy built on a very 2002 premise: a heartbroken San Francisco web designer swears off all sexual contact for the 40 days of Lent — right as he meets the perfect woman. Josh Hartnett at the peak of his heartthrob moment, opposite Shannyn Sossamon.
Every morning is Sunday, October 13, and every morning Henry has to make Lucy fall in love with him again. Adam Sandler and Drew Barrymore's Hawaiian reunion gave 2004 the Good Morning Lucy tape, Ten-Second Tom, a walrus named Jocko and 311's reggae-tinged cover of The Cure, and left a trail of remakes from Telugu to Japanese.
Hilary Duff waits tables at her wicked stepmother's San Fernando Valley diner while trading anonymous messages with a soulmate — who turns out to be Chad Michael Murray, the most popular boy in school. Critics hated it; an entire generation of sleepovers overruled them.
The love fern, the scrapbook of future children, the Knicks game she ruins and the yellow dress. Kate Hudson and Matthew McConaughey each ran a bet on the other for ten days in the 2003 rom-com that critics shrugged at and audiences graded A-minus.
The megawatt smile that owned the 90s box office. From Pretty Woman through Notting Hill and Runaway Bride, Julia Roberts was the romantic-comedy lead every studio wanted and every video store shelved face-out — then she capped the run by winning the Oscar as Erin Brockovich.
A modern Pygmalion: class president bets he can turn an art-nerd girl into prom queen in six weeks. Released January 29, 1999, directed by Robert Iscove, it became the surprise smash that crowned the entire late-90s teen-movie wave. A staircase reveal, a perfect song, and one of the era's most-rewatched moments.
Tom Hanks is a widowed architect whose eight-year-old son calls a radio show on Christmas Eve; Meg Ryan is the Baltimore reporter who hears it and can't let go. Nora Ephron's 1993 romantic comedy sent a generation to the top of the Empire State Building on Valentine's Day, with a standards soundtrack that hit number one.
Adam Sandler as Robbie Hart, a 1985 wedding singer dumped at the altar, and Drew Barrymore as the waitress he writes "Grow Old With You" for. The film that proved Sandler could be sweet, and the first pairing of two stars who kept coming back to each other.