The Best Romantic Comedies Of The Past 30 Years
Grab the popcorn!
Romantic comedies are the comfort foods of movie watching. Sure, the plots may be predictable at times and the endings are typically too good to be true, but putting on a rom-com that you can quote from start to finish is like throwing on your favorite blanket.
There have been countless great romantic comedies since the early days of cinema, but the genre has been particularly strong since the 1980s. We’ve rounded up the best English-language rom-coms to warm our hearts in the last 30 years, based on factors including Rotten Tomatoes critic scores, IMDB fan voting, Oscar consideration, box-office grosses and enduring popularity.
Take a look at our list, which is presented in alphabetical order because you can pretty much choose any of them and you’ll have a great night.
’10 Things I Hate About You’ (1999)
The earnest performances of Julia Stiles and the late, great Heath Ledger make “10 Things I Hate About You” one of the best teen romances of the ’90s. Following in the footsteps of 1995’s “Clueless” — which we’ll get to later — this film took Shakespeare’s “The Taming of the Shrew” and told it in the setting of an American high school.
Stiles played Kat Stratford, an idol for all antisocial girls, who must get asked on a date in order for her popular younger sister to be allowed to have a dating life. The stellar cast also included Joseph Gordon-Levitt, Gabrielle Union and Allison Janney. Nineties teens look at this film like ‘80s teens look at a John Hughes movie.
‘500 Days of Summer’ (2009)
This indie darling told its story in an interesting way and ended up earning a ton of money and critical acclaim as a result. It followed a 500-day relationship between characters played by Joseph Gordon-Levitt and Zooey Deschanel, but was told completely out of order, bouncing back and forth through their time together.
It helped make Deschanel into a star who would get her own network TV show two years after the film premiered, and it continued Gordon-Levitt’s career as an adorable everyman. “500 Days of Summer” holds down very respectable scores on Rotten Tomatoes (86 percent) and IMDB (7.7) and is a great choice for people who don’t like typical rom-coms.
‘About A Boy’ (2002)
The first of many Hugh Grant star vehicles on this list, “About a Boy” was one of those rare romantic comedies that made critics swoon as much as audiences. This offbeat movie followed Grant as an aloof, immature man who looks for love after becoming friends with a wise young boy.
“About a Boy” maintains an outstanding 93-percent rating at Rotten Tomatoes, raked in plenty of money in theaters and even earned an Oscar nomination. Along with Grant, the impressive cast includes Rachel Weisz, Toni Collette and Nicholas Hoult as the boy.
‘As Good As It Gets’ (1997)
You won’t find many rom-coms led by a character as unlikable as Jack Nicholson’s offensive, OCD-suffering grouch in “As Good as It Gets.” This surprisingly sweet and grown-up film followed Nicholson as a homebody author who slowly realizes he has feelings for a stressed-out waitress played by Helen Hunt.
The acting and writing in this movie are a dream, leading to Oscar wins for Nicholson and Hunt, plus it features pitch-perfect performances from Greg Kinnear and Cuba Gooding Jr. If you like your romantic movies to carry a little more weight, “As Good as It Gets” is a perfect choice.
‘The Best Man’ (1999)
Featuring a who’s-who cast of young black stars — including Taye Diggs, Morris Chestnut, Terrence Howard and Nia Long — “The Best Man” became an indie hit with audiences in 1999. The story follows a group of old friends who get together when one is about to be married and personal secrets soon come to light.
Diggs was one of the it-men of Hollywood romance in the late 1990s/early 2000s and he proved why with his charming performance and devastating looks here. In 2013, the talented cast and director would reunite for “The Best Man Holiday,” which was also loved by critics and fans of the original.
‘The Big Sick’ (2017)
One of the newest movies on this list, 2017’s “The Big Sick” immediately took its place among Hollywood’s greatest rom-coms. The film followed the real-life love story of actor Kumail Nanjiani and writer Emily V. Gordon, who co-wrote the screenplay together (which earned them an Oscar nomination).
The plot focuses on the culture clash of a Pakistani-American man and his American girlfriend, as well as the difficulties they face when she gets sick. According to Rotten Tomatoes, “The Big Sick” is the second-best romantic comedy of all time, only ranking behind 1934’s legendary “It Happened One Night.”
‘Bridget Jones’s Diary’ (2001)
This hilarious, R-rated romance boasted an all-star cast of Renée Zellweger, Hugh Grant and Colin Firth, plus a script lifted from Jane Austen. Loosely based on “Pride and Prejudice,” “Bridget Jones’s Diary” follows a British woman who keeps brutally honest journals about her life as a single 30-something.
Bridget’s innermost thoughts are as raw and funny as anything you’ll hear in a romantic comedy, and they only make you love the character more. Two more sequels have hit theaters since this one became a hit in 2001, proving audiences still want to know what’s happening in her messy love life.
‘Bull Durham’ (1988)
The oldest movie on our list, “Bull Durham” is the rare American rom-com that’s aimed more at male audiences than at female audiences. It follows a veteran minor-league baseball player and his relationship with a woman who loves the game as much as he does. This is one of the coolest movies on the list, thanks to the effortlessly sexy performances of Kevin Costner and Susan Sarandon.
It currently holds down a 97-percent Rotten Tomatoes score and is as beloved by sports fans as it is by people who just enjoy a good romance. In 2003, Sports Illustrated named it the greatest sports movie of all time.
‘Chasing Amy’ (1997)
Another one that’s perfect for people who don’t like sappy romance, “Chasing Amy” is a great portrayal of Generation-X attitudes toward love in the ‘90s. “Clerks” filmmaker Kevin Smith filled “Chasing Amy” with his signature dialogue that’s packed with cursing and pop-culture references.
The story follows a man who falls for a comic book artist who is a lesbian. The unique script and raw performances by young Ben Affleck and Joey Lauren Adams make this more arresting than your average rom-com.
The influence of “Clueless” on other teen movies that would follow it is immeasurable. This modern-day retelling of Jane Austen’s “Emma,” set in a posh Beverly Hills high school, would inspire an entire generation of similar adaptations aimed at teens.
Alicia Silverstone’s lead performance as the vapid-but-lovable meddler Cher Horowitz is just one reason why “Clueless” went on to be a major hit in 1995. The valley-girl lingo in its script and charming performances by a young Paul Rudd and the late Brittany Murphy also make this a must-see.
‘Crazy Rich Asians’ (2018)
The newest movie on this list, “Crazy Rich Asians” is still playing in theaters as of publication time, yet it has already joined the list of all-time classic romantic comedies. This surprise blockbuster, based on a novel by the same name, follows a professor who travels from America to Singapore with her boyfriend, where she learns his family is ridiculously wealthy.
A major success story in the call for diversity in Hollywood, nearly all the top cast and crew members of “Crazy Rich Asians” are Asian-Americans. Audiences are clearly loving this one, making it the highest-grossing rom-com to come out of Hollywood in about 10 years, as of Oct. 1. Critics have been equally smitten, giving it a 92-percent score on Rotten Tomatoes.
‘Crazy, Stupid, Love.’ (2011)
If you love NBC’s “This is Us” — and how couldn’t you? — you might be a fan of 2011’s “Crazy, Stupid, Love,” which came from the same writer. Like that hit show, this movie follows a large cast of characters as they navigate their love lives.
The cast is packed with A-list talent like Emma Stone, Ryan Gosling, Steve Carell, Julianne Moore and Kevin Bacon. It’s a very sweet movie that gave filmgoers some gratuitous shots of Gosling with his shirt off … if you’re into that sort of thing.
‘My Big Fat Greek Wedding’ (2002)
Did you know “My Big Fat Greek Wedding” is the highest-grossing romantic comedy ever made? That shows just how charming this 2002 classic is, in case you haven’t had the pleasure of getting to know its lively cast of characters.
The film, starring and written by Nia Vardalos, tells the story of a Greek-American woman who falls in love with a non-Greek man who must get to know her massive family. Few of the movies on this list will make you laugh as hard as “My Big Fat Greek Wedding.”
‘Notting Hill’ (1999)
The combined rom-com prowess of Hugh Grant and Julia Roberts is almost too much for a single movie to handle. “Notting Hill” follows the unlikely romance between a Hollywood star, played by Roberts, and the owner of a small bookstore, played by Grant.
The two stars were at their peaks when it debuted in 1999 and critics and audiences loved it. This likable and funny film has been called a “perfect date flick.”
One of Disney’s most experimental movies, “Enchanted” is a fun romantic comedy for all ages. It features a mix of animation and live-action, and its plot follows a princess who must adapt to life outside her storybook world when she’s banished to New York City.
It’s a loving tribute to Disney’s animated classics and features narration by Julie Andrews, as well as original songs by the guys who wrote the music for “Beauty and the Beast,” “Aladdin” and other favorites. “Enchanted” was nominated for three Oscars and holds a 93-percent Rotten Tomatoes score, thanks in part to an endlessly lovable performance by Amy Adams.
‘There’s Something About Mary’ (1998)
If you like your rom-coms a bit more raunchy, “There’s Something About Mary” is a must-see ‘90s classic. The love story, about a group of men who are all in love with a charming woman named Mary, has its share of genuinely sweet moments but is also full of R-rated gags that may gross you out.
Cameron Diaz was born to play Mary and co-stars Ben Stiller and Matt Dillon also embody their roles perfectly. Who knew the guys who made “Dumb and Dumber” would be responsible for one of the best romantic movies ever made?
‘When Harry Met Sally…’ (1989)
This might be my personal favorite on the list. The timeless “When Harry Met Sally…” told its love story in an unconventional way by leaving viewers to hold their breath wondering if the two main characters would ever get together.
It follows Harry, played by Billy Crystal at his snarkiest, and Sally, played by Meg Ryan at her most lovable, as they bump into each other over the course of 12 years in New York at various stages in their lives. The smart script by the great Nora Ephron, full of quotable dialogue and deep truths about adult life, is what separates this one from others on the list.
‘Enough Said’ (2013)
One of the more overlooked entries on this list, 2013’s “Enough Said” was the rare romantic comedy that starred middle-aged actors playing middle-aged characters. It’s about the romance that buds between a divorced woman and a man who turns out to be her friend’s ex-husband.
At the top, it features two of the best TV actors of all time in Julia Louis-Dreyfus and James Gandolfini, who are joined by other greats like Catherine Keener and Toni Collette. If you like realism and maturity in your rom-coms, check out “Enough Said.”
‘Forgetting Sarah Marshall’ (2008)
People who like their romantic comedies a little raunchy will love “Forgetting Sarah Marshall.” This hilarious, R-rated movie follows a heartbroken man who goes on a Hawaiian vacation to get over his ex-girlfriend … who happens to be staying at the same resort.
Jason Segel of “How I Met Your Mother” steals the movie with his vulnerable — and incredibly revealing — performance, but co-stars Mila Kunis, Kristen Bell and Russell Brand are equally great. You might not laugh harder during any rom-com on this list.
‘Four Weddings And A Funeral’ (1994)
Among the most acclaimed movies of the ‘90s, “Four Weddings and Funeral” helped make Hugh Grant into the rom-com icon he would become. This British film follows the whirlwind romantic lives of a group of friends.
Grant and Andie MacDowell lead the film, which also features Kristin Scott Thomas and Rowan Atkinson. “Four Weddings and a Funeral” made a killing at the box office and was a hit with critics, holding down a 95-percent score at Rotten Tomatoes.
‘Garden State’ (2004)
When “Garden State” rolled to box-office success from first-time writer/director Zach Braff, it became one of the biggest surprises of 2004. The movie is still beloved as an offbeat rom-com aimed at restless 20-somethings.
It is the story of a young man who returns to his hometown in New Jersey after his mom dies and discovers a kindred spirit in an eccentric young woman who lies constantly. The chemistry between Braff, who also starred, and the always-great Natalie Portman made “Garden State” an instant favorite. Oh, and it also has an awesome soundtrack that won Braff a Grammy.
‘Groundhog Day’ (1993)
There may never be a more high-concept romantic comedy than 1993’s immortal “Groundhog Day.” It follows a smug TV meteorologist who slowly falls in love with his producer as he is forced to live out the same day over and over while on assignment in a small town.
Bill Murray stars as the weatherman in one of his most beloved roles and Andie MacDowell plays his producer. It’s clearly still loved by fans, holding an impressive 8.0 grade from IMDB voters, making it one of the highest-rated romantic movies ever made.
‘Lars And The Real Girl’ (2007)
Speaking of high-concept rom-coms, this Ryan Gosling film has one of the most bizarre plots of any on this list. “Lars and the Real Girl” is about a man who carries on a romantic relationship with a realistic-looking sex doll named Bianca.
It could have been a disaster but Gosling’s kindhearted performance and the sweet script make it one of the best-reviewed movies on this list. If you like indie movies and aren’t typically into rom-coms, you might find yourself loving this hidden gem.
‘Love Actually’ (2003)
A modern Christmas classic, “Love Actually” belongs on this list if only for its epic cast of incredible actors. The ensemble includes Hugh Grant, Colin Firth, Emma Thompson, Laura Linney, Alan Rickman, Keira Knightley and Liam Neeson in arguably his sweetest role ever.
It follows 10 different love stories that play out during the holiday season in England, intertwining in various ways. Richard Curtis, the writer and director of “Love Actually,” also wrote three other movies on this list, making him one of the masters of romance in the last few decades.
‘Love Jones’ (1997)
It’s sad to think that, in 1997, “Love Jones” was considered groundbreaking simply because it portrayed a romance between black characters in a realistic, mature way. Larenz Tate and Nia Long lead the cast, which also includes Bill Bellamy and “Grey’s Anatomy” star Isaiah Washington.
It follows a poet and a photographer who meet in a Chicago nightclub and fall in love. It is beloved by audiences, boasting an amazing 97-percent audience score at Rotten Tomatoes, as well as a 7.5 from IMDB voters.
‘Love, Simon’ (2018)
The only rom-com that follows a gay lead character on our list — and, sadly, one of the only ones to ever be made — “Love, Simon” became a surprise hit with audiences and critics in 2018. Its plot follows a closeted gay teen named Simon who tries to figure out the identity of a fellow student he’s fallen in love with online.
Featuring a likable cast led by Nick Robinson and Jennifer Garner, “Love, Simon” has a lot of the heart and spirit of John Hughes’ best teen movies. This one is really funny, honest and sweet, with a love story that you can’t help but be warmed by during the film’s satisfying conclusion.
‘Moonrise Kingdom’ (2012)
No rom-com on our list features a love story between younger characters than “Moonrise Kingdom.” This sweet film follows two restless 12-year-olds who run away together after falling in love as pen pals.
The two child stars, Jared Gilman and Kara Hayward, are wonderful together, and the adult cast is incredible, featuring legends like Bruce Willis, Bill Murray and Francis McDormand. All the wonder and adventure of adolescence is here, making for one of the most memorable romantic comedies ever made.
‘Pretty Woman’ (1990)
Who’d expect a movie about a prostitute to become one of the most iconic romantic comedies of all time? The palpable sexual chemistry between Julia Roberts and Richard Gere is what elevates “Pretty Woman” to the top of the genre.
It follows a Hollywood prostitute who ends up as the love interest of a rich businessman in just a matter of days. If you want a grown-up love story that still maintains a bit of sappy innocence, “Pretty Woman” is a great choice.
‘Say Anything…’ (1989)
Writer/director Cameron Crowe has made some solid romantic films in the past 30 years, but his first one is the only to make this list. “Say Anything…” is about an underachieving high school student who falls for the valedictorian and starts an unlikely summer relationship with her.
The film’s soundtrack, like many ’80s teen flicks, is outstanding and only adds to the nostalgic appeal of “Say Anything…” Critics and audiences love this romance equally, with it holding a near-perfect 98-percent score at Rotten Tomatoes and a fantastic 7.4 at IMDB.
‘Working Girl’ (1988)
Some of the best romantic comedies are also about one character’s journey of self-discovery; 1988’s “Working Girl” is one of those films. It’s about an ambitious Wall Street secretary who sneakily advances her career while also striking up a relationship with a charming executive.
The all-star cast includes Melanie Griffith as the spirited lead, Harrison Ford as her love interest and Sigourney Weaver, Alec Baldwin and Joan Cusack as supporting characters. “Working Girl” was one of those rare rom-coms to be a critical powerhouse, raking in five Oscar nominations to go with one win.