Time to feel old, ’90s kids: Never Been Kissed turns 20 this week.
Drew Barrymore, coming off her 1998 hit The Wedding Singer, gave one of her best performances as an awkward journalist going undercover at her old high school — a very familiar romantic comedy trope. Never Been Kissed is just one of the great rom-coms the ’90s gave us, with the decade kicking off with the Julia Roberts-Richard Gere classic Pretty Woman. To celebrate “Josie Grossie’s” 20th anniversary, here are a few more great ’90s rom-coms that will give you all the nostalgia.
1. ‘Pretty Woman’ (1990)
Has a star ever come out so fully formed as Julia Roberts did in this ’90s hit?
Her charming and insanely likable turn as the prostitute with a heart of gold who wins over Richard Gere’s rich businessman is as iconic as the movie itself. Granted, the movie’s storyline doesn’t quite hold up in 2019, but the effortless chemistry between its two leads still does.
2. ‘Sleepless In Seattle’ (1993)
Tom Hanks and Meg Ryan became the rom-com king and queen here in this hit from Nora Ephron. Hanks’ widower, with the help of his son, Jonah, finds love again with the help of a radio call-in show that links him to Meg Ryan’s reporter character. (The genre LOVES a reporter-falling-in-love trope).
Despite the film’s intermittently plodding pace, Sleepless In Seattle effortlessly toggles between LOLs and tearjerker moments in a way that only the late Ephron could.
3. ‘Four Weddings and a Funeral’ (1994)
Another essential ’90s movie, Four Weddings recently celebrated its 25th anniversary and it’s a genre staple that is as funny now as it was then.
The movie that made Hugh Grant a star and turned writer Richard Curtis into, well, RICHARD FREAKIN’ CURTIS, Four Weddings chronicles a core group of friends as they deal with the messiness of relationships across the titular event. Curtis’ crazy-sharp signature wit, and character-first storytelling, elevates the title to all-timer status, as does the engaging dynamic between Grant’s character and the object of his affections, played by a never-better Andie McDowell.
4. ‘The American President’ (1995)
Screenwriter Aaron Sorkin’s dry run for The West Wing, The American President is one of those ’90s movies that doesn’t get the attention it deserves.
Michael Douglas is a single dad who happens to be President of the United States, struggling with Washington politics and the dating scene as he falls for political strategist Sydney Allen Wade (Annette Bening). Future West Wing POTUS Martin Sheen leads a strong ensemble of supporting characters, but it’s Bening’s performance that steals the show. She gives each scene the exact amount of whatever it needs to help endear her and her character’s relationship with the President to audiences.
5. ‘Muriel’s Wedding’ (1994)
Look, if you haven’t seen this exceptional movie yet, then fix that ASAP.
Australian director P.J. Hogan, who would go on to direct My Best Friend’s Wedding, introduced U.S. audiences to the endless supply of talent that is lead actress Toni Collette. Here, she plays Muriel, a socially-awkward type with ambitious dreams of a big wedding and an even bigger life for herself outside the confines of her dead-end small Aussie town. Lots of laughs and drama ensue, proving why Muriel’s Wedding earned its critical and box office success.
6. ‘While You Were Sleeping’ (1995)
’90s Sandra Bullock was a national treasure — don’t even try to fight us on it. She cemented that status with a one-two punch of 1994’s action hit Speed and 1995’s While You Were Sleeping, the best rom-com on the star’s list of credits.
Bullock is charming AF here, so much so that you don’t really mind that she pretends to be engaged to a coma patient and falls for both his family and his brother.
7. ‘My Best Friend’s Wedding’ (1997)
One of the biggest and most popular hits of Julia Roberts’ career, My Best Friend’s Wedding is a staple for many a ’90s kid.
Sure, Roberts is both hero and villain in this rom-com that finds her pining for her best friend (Durmott Mulroney) a few days before he is set to wed Cameron Diaz, and she does some truly garbage things to thwart her friend’s happiness in favor of her own. But, somehow, legions of fans were able to look past that and fall for Roberts’ character — and that “Say a Little Prayer for You” singalong — and turn Wedding into one of the genre’s most unforgettable entries.
8. ‘You’ve Got Mail’ (1998)
Tom Hanks and Meg Ryan reunite with their Sleepless In Seattle writer-director Nora Ephron for a love story that more than holds up 20 years later — well, minus all the AOL email usage.
Inspired by the 1940 classic The Shop Around the Corner, You’ve Got Mail is Hollywood’s first take on online dating as Joe Fox (Hanks) falls for Kathleen Kelly (Ryan) with the help of their AOL accounts, and neither one of them know they are each other’s professional rivals in the bookstore business. (Okay, this whole bookstore thing doesn’t hold up now either). Despite the dated depiction and usage of the ’90s internet, fans of Hanks and Ryan’s chemistry will not be disappointed as the two’s courtship features some of their funniest work.
9. ‘Blast From the Past’ (1999)
If there’s anything better than ’90s Brendan Fraser, we don’t wanna know about it.
Proof positive that this decade was where the rom-com genre could take some of its biggest swings, Blast From the Past centers on Fraser’s 35-year-old Adam emerging from a Cuban Missile Crisis-era bomb shelter in then-modern day 1997. He soon falls for Eve (Alicia Silverstone) in this man-out-of-time romance that is a hidden gem amongst the genre’s considerable ’90s output. Christopher Walken as Adam’s dad is worth the rewatch alone.
10. ‘Never Been Kissed’ (1999)
We’re a sucker for a late-20s/early-30s reporter forced to pose as a high school student in order to get their story. While the plot device has often been done, with various degrees of success, Never Been Kissed is one of the better takes on it, thanks in large part to Barrymore’s full buy-in to the movie’s premise. Like in Wedding Singer before this, her quirky charms are infectious and make it impossible for audiences not to root for Josie to finally get the love she deserves. There’s a reason why ’90s kids stan this movie so hard.
11. ‘Notting Hill’ (1999)
Julia Roberts both started and ended the decade with two of her best and most popular films.
Four Weddings‘ writer Richard Curtis directs his own script, which finds UK-based travel bookshop owner Hugh Grant caught up in a challenging romance with Hollywood star Anna Scott, played by Roberts — who seems to be drawing from her personal life as her character struggles to find love among the scrutiny of paparazzi’s flashbulbs.
Clever dialogue and exceptional chemistry are the beating heart of Notting Hill, which will make you swoon — and reach for the tissues — when Anna gives her iconic “I’m just a girl…” speech.