While you've probably seen "Notting Hill" or "10 Things I Hate About You" a million times, there are some underrated films that deserve a watch (or re-watch).
15. One Fine Day (1996)
George Clooney as a suave journalist, Michelle Pfeiffer as an overworked single mom, both of their kids miss a field trip, and voila! Fate throws them together for a day of juggling work and childcare.
Clooney's Jack takes a laid-back approach, while Pfeiffer's Melanie is a schedule-obsessed planner. Chaos, obviously, ensues. They have to share babysitting duties while trying to salvage their respective careers. Sparks fly, but not without some resistance.
14. The Truth About Cats & Dogs (1996)
Janeane Garofalo plays Abby, a smart and witty radio host who gives pet advice. Uma Thurman is her stunning but somewhat dimwitted neighbor Noelle.
When a listener, played by Ben Chaplin, falls for Abby's voice, she sends Noelle as her stand-in because she's insecure about her looks. Imagine trying to woo someone through another person's body: of course, complications multiply fast.
13. Two if by Sea (1996)
Sandra Bullock and Denis Leary star as Roz and Frank, a couple that's basically on the run after Frank steals a painting. They hole up in a quaint little New England island with the plan to sell the painting and hopefully solve all their financial woes.
The island is full of quirky, wealthy vacationers, one of whom takes quite an interest in Roz. Amid dodging the FBI and navigating this potential love triangle, Frank begins to wonder what Roz truly wants – money or a fresh start?
12. French Kiss (1995)
Meg Ryan plays Kate, an American woman terrified of flying, who musters the courage to fly to France when her fiancé falls for a French woman. Kevin Kline is Luc, a charming but irritating Frenchman who gets entangled in her quest. The two of them traverse France in a wild goose chase involving grapes, smuggled diamonds, and a lot of bickering. All that tension has to go somewhere, right?
11. Beautiful Girls (1996)
This one centers around a piano player, Willie, who returns to his hometown for a high-school reunion and catches up with old friends and flames. He's got a girlfriend but starts feeling a deep emotional connection with Marty, his neighbor's 13-year-old daughter. Nope, not romantic but it forces him to rethink what he wants in a relationship.
Meanwhile, his friends are dealing with their own romantic dilemmas – marriages on the brink, unrequited love, and the like.
10. Living Out Loud (1998)
Holly Hunter plays Judith, a divorcee learning to navigate her new life. She strikes up an unusual friendship with her building's elevator operator Pat, played by Danny DeVito. Judith also explores a complicated relationship with her hot but emotionally unavailable neighbor. Instead of just sulking, she starts going to a nightclub to find herself, encountering a quirky cast of characters along the way.
9. Next Stop Wonderland (1998)
Hope Davis plays Erin, a nurse who gets dumped and finds herself reluctantly back on the dating scene. Her mom places a personal ad for her, and voila, the dating disasters commence. Meanwhile, there's Alan, an aspiring marine biologist who keeps crossing paths with Erin but never actually meeting her. It's a dance around destiny, but will they finally collide?
8. The MatchMaker (1997)
Marsha, played by Janeane Garofalo, is a political aide sent to Ireland to find her boss's family roots, aiming to exploit them for electoral support. While she's busy digging through the Irish soil, the town is in the middle of a matchmaking festival. Cupid aims his bow, and Marsha finds herself torn between her job and a local journalist.
7. Don Juan DeMarco (1994)
Johnny Depp plays a young man who believes he's Don Juan, the world's greatest lover. Marlon Brando is the psychiatrist trying to treat him. But here's the irony: Brando's character starts getting seduced by the romantic tales and rekindles romance with his own wife.
It's less about laugh-out-loud comedy and more a feel-good, whimsical take on love.
6. Fools Rush In (1997)
Matthew Perry and Salma Hayek star in this culture-clash comedy. Perry plays Alex, a straight-laced guy who has a one-night stand with free-spirited Isabel, played by Hayek. A few months later, Isabel is pregnant, and they decide to give marriage a shot. What follows is a whirlwind of family antics, cultural differences, and the realization that love isn't a straight path.
5. Addicted to Love (1997)
Meg Ryan plays Maggie, and Matthew Broderick is Sam, both scorned by their exes who are now dating each other. They team up to spy on and sabotage the new couple. As you might guess, while plotting revenge, Maggie and Sam grow close. But can a relationship built on scheming really work out?
It's a darkish rom-com that plays out like an anti-Valentine's Day fantasy.
4. It Could Happen to You (1994)
Nicolas Cage plays Charlie, a New York City cop, and Bridget Fonda is Yvonne, a waitress. Charlie's low on cash but wants to leave a tip, so he promises to give Yvonne half the winnings if his lottery ticket is a hit. Well, luck be a lady, the ticket wins! True to his word, he splits the multi-million dollar jackpot with her.
The feel-good story turns into tabloid fodder, complicating his relationship with his money-hungry wife, Muriel.
3. Picture Perfect (1997)
Jennifer Aniston plays Kate, a single, career-driven woman who fakes having a fiancé to get ahead at work. Jay Mohr is the guy she ropes into playing the part. They agree to a business-like arrangement, but – surprise, surprise – feelings get involved.
With a fake engagement, work drama, and actual chemistry, what could possibly go wrong, right?
2. Home Fries (1998)
Drew Barrymore and Luke Wilson star in this quirky little comedy. Sally, played by Barrymore, is a pregnant fast-food worker who gets involved with Dorian, played by Wilson. Little does she know, Dorian is the stepson of her baby's father. When the baby daddy dies in a suspicious "accident," secrets start unraveling.
1. Chasing Amy (1997)
Ben Affleck plays Holden, a comic book artist who falls hard for Alyssa, a lesbian played by Joey Lauren Adams. They become friends, but Holden can't shake his feelings and eventually confesses. Despite the initial shock and resistance, Alyssa reciprocates, but their unconventional relationship brings its fair share of challenges.