While the 1990s are known for plenty of things, such as bad — or as some would say, eclectic — fashion and hardcore alternative music, one of the best parts of the decade is definitely all the amazing romantic comedies that graced our screens. Sure, some favorites really fail the test of time, but others still hold up as some of the best films of all time. Since then, the romantic comedy genre continued to come out with more hits in the 2000s, before romcoms seemed to disappear as we transitioned into the 2010s, as the entertainment industry and audiences’ desires shifted.
Thankfully, there’s a true revival of romantic comedies happening right now with more diverse and progressive stories, with a few fantastic films of the past few years including Crazy Rich Asians, Booksmart, and To All the Boys I’ve Loved Before. Still, it’s hard to say yet if this new period of romcoms can compete with the classics of the 1990s. So which 90s romantic comedies earn a spot on this list? Let’s take a trip down memory lane as we rank the 25 best 90s romantic comedies.
25. Drive Me Crazy
Maybe this is completely driven by nostalgia, but for some reason Drive Me Crazy feels like it fully embodies what teenagers in the late 90s were obsessed with. Melissa Joan Hart was at an all-time high in her career, and somehow she meshes really well with Adrian Grenier, who was the total alternative 90s heartthrob with a mop of dark hair and a sarcastic yet charming personality. With a classic fake dating to real love trope, popular perfectionist Nicole (Hart) teams up with her troublemaker neighbor Chase (Grenier) to make their exes and enemies jealous. Written by Rob Thomas, the creator of hit television series like Veronica Mars and Party Down, the jokes are witty and fast-paced, the romance sweet, and the movie has amazing side characters, particularly Chase’s best friends Ray (Kris Park) and “Designated Dave” (Mark Webber).
24. Can’t Hardly Wait
Starring Ethan Embry as Preston, a high schooler planning to profess his love for long-time crush Amanda (played by Jennifer Love Hewitt) at the big graduation party, Can’t Hardly Wait is remembered as a major 90s rom-com film that showcases teenagers of the era. But that’s just it. It’s remembered as a great movie, but looking back now, Can’t Hardly Wait is kind of problematic, starting with the concept of a “nice guy” thinking he deserves the pretty girl he barely knows and ending with a lot of casual homophobia. Despite this, you can’t help but relate to Amanda’s plight to simply date someone who likes her for her mind and not her looks, and in the end, Preston proves that he’s actually a good guy. The movie has many bright spots, such as the awkwardly adorable love of Kenny (Seth Green) and Denise (Lauren Ambrose), the unbelievable cast that includes Jaime Pressly, Selma Blair, and Jason Segel, and the great soundtrack. Keeping the time period in mind and considering the lasting impact of the movie, we will allow Can’t Hardly Wait to stay a problematic fave.
23. She’s All That
She’s All That is another movie that probably wouldn’t be made today in exactly the same way (we’re going to ignore Netflix’s attempt at a modern, gender-swapped version), but no one can deny how amazing this pairing of Freddie Prince Jr. and Rachel Leigh Cook is. Add to that a bad boy Paul Walker and a self-obsessed reality star played by Matthew Lillard, and what more do you need? While we certainly don’t condone making bets about manipulating teenage girls like Zack (Prince Jr.) does with Laney (Cook), the movie makes up for it with Zack and Laney’s adorable romance and clear chemistry, as well as the amazing supporting cast. Along with everyone already named, She’s All That also features Anna Paquin, Kieran Culkin, Gabrielle Union, Clea DuVall, Usher, and Lil’ Kim. Plus, don’t even try to pretend you didn’t act out the iconic hacky sack scene in your bedroom.
22. There’s Something About Mary
1998’s There’s Something About Mary is from the Farrelly brothers filmmaking team, who famously also helmed Dumb and Dumber, and you can definitely see the earlier film’s influence on the romantic comedy. The movie stars Ben Stiller as Ted Stroehmann, a teenager whose dream prom date with Mary Jensen, played to perfection by Cameron Diaz, ends before it even begins when he gets his scrotum stuck in his pants’ zipper. Yes, this is how the story begins, and the raunchy, out-there humor only gets more intense from there. 13 years later, Ted is still in love with Mary, so he tracks her down and attempts to win her back. When There’s Something About Mary came out, it was a rare romantic comedy that really pushed the boundaries of the genre. While it isn’t for everyone and definitely has some issues, most notably in its treatment of people with mental and physical disabilities, There’s Something About Mary paved the way for raunchy comedies like Bridesmaids and every Judd Apatow flick to be made.
21. Honeymoon in Vegas
Some people might be unaware, but Nicolas Cage was quite the romantic lead in the 90s and his performances still hold up. In 1992, Cage, Sarah Jessica Parker, and James Caan all starred in the movie Honeymoon in Vegas, a crazy comedy about a Las Vegas wedding gone wrong. Private Detective Jack (Cage) and his girlfriend Betsy (Parker) go to Las Vegas to elope, but instead of getting married, Jack loses a lot of money to a tricky gambler named Tommy (Caan) who has a thing for Betsy and is intent on making her fall in love with him. Trading the debt for a weekend with Betsy promising no funny business, the couple relents, and Tommy scoops Betsy up and flies her to Hawaii. Jack must then navigate Tommy’s maze of tricks and traps, as well as his own bad luck, in order to return to his girlfriend and finally get through their wedding ceremony as promised. Featuring Cage and Caan as two charming men vying for Betsy’s affection and a plane full of skydiving Elvises, well, Honeymoon in Vegas delivers laughs and romance in high quantity.
20. Pretty Woman
A story about a beautiful sex worker named Vivian Ward (Julia Roberts) who is hired by the wealthy Edward Lewis (Richard Gere) to pretend to be his girlfriend for a week, Pretty Woman is a favorite rom-com for many, and for good reason. Roberts is stylish and supremely charming in the film, and at first glance, it feels like the perfect Cinderella story. But looking at Pretty Woman from a modern point of view, the film fails in its portrayal of both sex workers and sexual assault, showing Vivian as a woman in need of rescue from a rich, white man. And honestly, she’s way too good for Edward. But it’s really hard to hate a movie that stars Roberts, and the shopping scene when Vivan tells off the saleswoman, as well as Roberts’ legendary laugh at the necklace gag, remain iconic moments in rom-com history. Even Edward manages to win the audience over, with Vivian teaching him a thing or two about love and emotion. Pretty Woman’s influence on the romantic comedy genre is truly too strong to ignore.
19. Never Been Kissed
I can’t believe I’m saying this, but somehow Drew Barrymore’s charm overcomes all that’s wrong about this movie, at least to a point. Never Been Kissed, which came out in 1999, stars Barrymore as Josie Geller, a 25-year-old editor who pretends to be a high school student to learn more about current teenagers’ lives for an assignment. While there, Josie, who has never had a real relationship or even been kissed, as the title suggests, is able to have another shot at her high school days, becoming a part of the cool crowd and developing better self-confidence. Meanwhile, she starts falling in love with her English teacher, Sam Coulson, played by Michael Vartan, and he likes her back.
So yes, a relationship between a teacher and someone he believes to be underage is not something to promote. But considering this is a fictional story, Never Been Kissed actually does a pretty good job of forming Josie and Sam’s relationship in a respectful way, making sure Sam never does anything untoward and making it clear that Sam likes Josie for who she is, and not because of age or looks. Then there’s also that final scene on the baseball diamond, which gets your heart pounding in anticipation along with Josie’s as she watches the clock count down. Josie, I’m glad you finally got that kiss.
18. So I Married An Axe Murderer
So I Married An Axe Murderer stands out mainly because of the concept, merging murder mystery with a funny love story. What’s not to like? Mike Myers is the perfect actor for the role, someone who can amp up the humor while also allowing the audience to feel for his romance in spite of all the red flags. A beat poet in San Francisco (very 90s…), Myers’s character Charlie MacKenzie is scolded by his friends for constantly breaking up with women over small things, so Charlie gives it his all when he starts dating Harriet (Nancy Travis), and he quickly falls in love. Unfortunately, this relationship might actually have some real problems, as more and more signs point to Harriet being a husband murderer known as “Mrs. X.” As a love story, comedy, and murder mystery all in one, So I Married an Axe Murderer is an entertaining ride with a climactic final act to die for.
17. How Stella Got Her Groove Back
Starring Angela Bassett as Stella Payne, How Stella Got Her Groove Back, based on Terry McMillan’s novel of the same name, is about a 40-year-old businesswoman and mother who is finally convinced to take a well-deserved vacation to Jamaica, only to meet a younger man named Winston Shakespeare, played by Taye Diggs, who makes her rethink her life. Along with an amazing soundtrack featuring Stevie Wonder, Janet Jackson, Mary J. Blige, Boys II Men, and more, How Stella Got Her Groove Back is monumental for the empowering characterization of Stella, an older woman who has a successful career while raising a son who finally takes time for herself, discovering that she should also make her own happiness a priority. Also starring Whoopi Goldberg and Regina King, the 1998 film is fun, romantic, and total escapism for anyone who needs a good pick me up.
16. You’ve Got Mail
Directed by Nora Ephron, You've Got Mail stars Meg Ryan as Kathleen Kelly, a woman who runs an independent bookshop in New York City called The Shop Around the Corner, who first encounters Tom Hanks’s Joe Fox in an online chatroom. Joe is part of a family that runs a chain of big bookstores called Fox Books, and he’s opening up a new store right by Kathleen’s. Hiding their real identities, the two fall in love online, while the Kathleen and Joe of everyday life continue to butt heads. Eventually, the two worlds collide, and the couple must decide if the feelings they have are real or just an illusion from the internet.
Let’s just get this out of the way — You’ve Got Mail is a good movie, and Ryan and Hanks have the same great chemistry as they do in another film on this list (you know the one), but looking back, the film has some problems. Namely, Hanks’ character isn’t all that great, and his big company puts his love interest's independent bookshop out of business. But even though the capitalist ideas at play in You’ve Got Mail are a bit taxing, the romantic comedy is a fan-favorite that deserves the appreciation it gets. There’s obviously a reason Ryan and Hanks have been in so many movies together, and it’s because of their natural chemistry and acting talent. Seriously, even though Joe acts like a jerk sometimes, Hanks somehow makes it feel charming. You just can’t dislike Hanks, it’s that simple.
15. It Could Happen To You
The other Nicolas Cage movie on the list, It Could Happen To You is about a cop named Charlie (Cage) who doesn’t have enough money to tip his waitress, Yvonne (Bridget Fonda), so he promises her half of the money if his lottery ticket is a winner. Luckily for her, it is. Charlie is a good guy, so he plans to give Yvonne her promised money, but his wife Muriel (Rosie Perez) is having none of it. Directed by Andrew Bergman who also directed Honeymoon in Vegas, It Could Happen To You obviously leads to a romance between Charlie and Yvonne, but it naturally develops as those around the couple get greedy and earn a one-way ticket out of their lives. Overshadowed by some of his later, more extravagant performances, Cage’s performance in It Could Happen To You is subtle and sweet, and proves that he can definitely play a romantic leading man when needed. Hopefully someday soon he’ll return to the rom-com genre that started his career.
14. The Best Man
The Best Man stars Taye Diggs as the title character, Harper, an up-and-coming author whose first book, Unfinished Business, is a fictional retelling of many of his adventures with his group of college best friends. Unfortunately for Harper, his book is slowly getting passed around to his friends, all of whom will be at the wedding of his best friend Lance (Morris Chestnut), and his fiancée, Mia (Monica Calhoun). Arriving a few days ahead of his girlfriend Robyn (Sanaa Lathan), Harper desperately wants to keep his book away from Lance, as it reveals a one-night-stand between Harper and Mia that he’d rather keep secret. Meanwhile, flirtations with an old friend named Jordan (Nia Long) lead Harper to question his love for Robyn, as well as whether or not he ever wants to get married.
Along with being an R-rated comedy filled with romance and drama, The Best Man was a major milestone for Black representation on screen, showcasing real people dealing with realistic, everyday troubles, rather than overused racist stereotypes. This is particularly true for the male characters, with Diggs’s Harper being a creative, relatable guy who is just starting to find success in his career. But even without the cultural impact of The Best Man, the movie is an entertaining study on different types of relationships and what it feels like to face your college friend group after you’ve all started going in different directions.
13. But I’m A Cheerleader
Released in 1999 (2000 in the US, but screw technicalities) and directed by Jamie Babbit, But I’m A Cheerleader is a colorful, ambitious satire of religion, gender roles, and heteronormativity, and it’s almost a miracle this film was even made at all. Starring Natasha Lyonne as 17-year-old cheerleader Megan, the film follows the teenager through her experience at a conversion therapy camp where parents send their kids to go through a 12-step program to heterosexuality. There, Megan meets Graham, played by Clea DuVall, and the two fall in love as the whole camp begins to rebel. When But I’m A Cheerleader first came out, it was very negatively received by critics and audiences, but now more than twenty years later, the movie has become a cult classic. The trajectory of But I’m A Cheerleader is similar to Jennifer’s Body, another progressive movie held back by the entertainment industry when it was initially released, only finding the right audience years later. Along with the stellar performances of Lyonne and the rest of the cast, But I’m A Cheerleader is an intelligent, underrated romantic comedy that more people should check out.
12. My Best Friend’s Wedding
My Best Friend’s Wedding is an amazing romantic comedy in that the characters are extremely imperfect, and it destroys one very common rom-com trope. As you’ll see in many other romantic comedies from over the years, it’s always the girl or guy who realizes that they love their best friend at the last minute and comes running to ruin their wedding (I’m looking at you, Made of Honor). In My Best Friend’s Wedding, Julia Roberts plays Julianne Potter, a woman whose old friend Michael (Dermot Mulroney) — who she happens to have a marriage pact with — is getting married to Cameron Diaz’s Kimmy. Determined to get the man who she believes is rightfully hers, Julianne plots to break the happy couple up. In the end, she admits her feelings shortly before the wedding, but Michael and Kimmy go through with the wedding anyway, obviously. It’s a bit revolutionary for a romcom couple to not end up in love at the end of the movie, and Roberts is wonderful as the uniquely unlikable yet relatable Julianne.
11. Grosse Pointe Blank
A true underrated gem, Grosse Pointe Blank might be a movie that a lot of readers have never seen, and you should really remedy that immediately. Coming out the same year she played Matt Damon’s love interest Skylar in Good Will Hunting, Minnie Driver stars in Grosse Pointe Blank as Debi Newberry, opposite romantic comedy king John Cusack as Martin Q. Blank. The cast is impressive, also featuring Alan Arkin, Dan Aykroyd, and Joan Cusack. In fact, it almost has the entire Cusack family, as fellow siblings Ann Cusack and Bill Cusack also have small roles in the movie. In Grosse Pointe Blank, Cusack is a professional assassin who is drawn back to his hometown of Grosse Pointe for a job, just in time for his high school reunion. While there, Blank reconnects with his high school sweetheart, Debi, and he must fight off fellow assassins and federal agents as he falls in love with her all over again. Initially, the premise seems a little far-fetched, but both Cusack and Driver manage to ground the story, adding humor and real chemistry to make Grosse Pointe Blank a romantic comedy that stands out from the other cookie-cutter stories of the 90s.
10. Sleepless In Seattle
Released in 1993, five years before You’ve Got Mail, Tom Hanks and Meg Ryan play love interests in Sleepless in Seattle. Moving to Seattle with his eight-year-old son Jonah (Ross Malinger), Sam (Hanks) is grieving the loss of his wife to cancer. Encouraged by his son, Sam calls into a popular radio show to talk about his grief, touching the heart of a woman named Annie (Ryan) in Baltimore. Moved by what she hears, Annie writes a letter to Sam asking him to meet her on top of the Empire State Building on the upcoming Valentine’s Day. Although she decides not to send it, her friend does it for her, leading Jonah to read the letter and push his father to meet Annie. The film follows Annie and Sam’s separate lives as they fail at romance and try to move on, as outside forces continue to push them together. Sleepless in Seattle shines with the sweet relationship between Sam and Jonah, while also being quite amazing due to the two leads having great chemistry despite spending almost the entire movie apart.
9. Groundhog Day
Bill Murray isn’t the first person you’d think of to lead a romantic comedy, but somehow in Groundhog Day he’s the perfect man for the job. Murray plays Phil Connors, a weatherman in Punxsutawney, Pennsylvania who finds himself stuck in a time loop on February 2nd, covering the annual Groundhog Day event. Phil isn’t too into the whole celebration in the first place, and after doing it over and over again, well, his mood isn’t great. For a long while, Phil uses his unique situation to eat a bunch of food, commit crimes, take advantage of women, and do anything else he wants to without facing consequences.
Growing bored, Phil decides that the ultimate win would be convincing his co-worker Rita Hanson (Andie MacDowell) to sleep with him. While the story seems cool and romantic at first, Phil is somewhat predatory as he uses the situation to his advantage, and the story takes an even darker turn when Phil attempts suicide to get out of the time loop. The movie ends up being a much more complicated story of morality and happiness wrapped up in a simple rom-com. Of course, we all know the happy ending, with Phil developing clear values and falling in love with Rita, and you can’t help but root for them. But Groundhog Day is definitely worth a deeper look if you’ve got the time. Overall, the movie’s premise is unique and layered, and with Murray and MacDowell in the lead roles, two capable actors who can handle both drama and comedy, you can’t lose.
8. While You Were Sleeping
Starring Sandra Bullock and Bill Pullman, While You Were Sleeping follows Lucy (Bullock), a Chicago Transit Authority token collector who saves a random man’s life in an accident that causes him to go into a coma. Following the man, Peter (Peter Gallagher), to the hospital, a nurse mishears one of Lucy’s mumblings and assumes that she is his fiancée. Soon enough his family arrives and she is caught in the lie, unsure about how to reveal the truth. As Peter sits in a coma, Lucy, who lives a lonely life without family or friends, continues the charade and grows very close to Peter’s family, particularly his brother, Jack (Pullman). The story of While You Were Sleeping could’ve ended up feeling gimmicky and fake, but instead it’s a really touching story of Lucy’s connection to Peter’s family, helped by the fact that Peter spends most of the movie unconscious. While Bullock has starred in a lot of romcoms and unsurprisingly nails her performance in While You Were Sleeping as the very sweet Lucy, a young woman that you can’t help loving, Pullman has only been in a few. Honestly, it’s a shame that he hasn’t starred in more, as he’s a true charmer as Jack.
7. The Wedding Singer
Although Adam Sandler is probably best known for his work in straight comedies, he’s frequently teamed up with romcom regular Drew Barrymore for a movie or two in her main genre. While they have a few successful films together, The Wedding Singer is arguably the best. In the 1998 film (which is actually set in 1985), Sandler plays the title character, Robbie Hart, an aspiring rock musician who works as a wedding singer to make ends meet. One day, he meets a cute waitress named Julia Sullivan (Barrymore) and promises to sing at her upcoming wedding. After his own wedding fails, he wants to pull out of the deal, but Julia convinces him to help her plan the event. As Robbie spends time with Julia, he slowly starts falling in love with her, angry at the thought of her marrying her schmuck fiancé. With a grand final act that features Robbie serenading Julia, a fight on a plane, and Billy Idol, The Wedding Singer has real style, and Sandler and Barrymore continue to prove just how much chemistry they have. There’s so much to love about The Wedding Singer, and it remains many fans’ favorite romcom even now.
6. Love Jones
Love Jones stars Larenz Tate as Darius Lovehall, a young poet in Chicago who becomes infatuated with Nia Long’s Nina Mosley, a photographer. While Nina claims that she’s not looking for anything, Darius is nothing if not persistent, and he quickly breaks her down and the two begin to date. Their relationship is practically perfect, but neither one knows if it’s supposed to be serious or not, and they have trouble admitting that they want it to be. Love Jones, which came out in 1997, is not just an amazing story of Black love, but it’s also a sweet, enjoyable romance all on its own. About two artists falling in love in 90s Chicago, there’s something special about Love Jones, with an expansive cast that also includes Isaiah Washington and Lisa Nicole Carson. Like The Best Man, Love Jones has helped push Black love to the forefront of the romantic comedy genre, and years later, the underappreciated film still holds up as a simple story of love.