Rom-coms combine the best of both worlds: love and laughter. So when we set out to find the best romantic comedies of all time, there were dozens of beloved rom-coms to choose from. From Meg Ryan classics like Sleepless in Seattle and When Harry Met Sally to newer flicks like Crazy Rich Asians and Palm Springs, rom-coms have been around for decades (or even centuries, according to some experts who consider Shakespeare plays some of the best romantic comedies), so to come up with our own list of the best romantic comedies was no easy feat.
But what makes a rom-com? Well, it’s more than a funny romance movie or a comedy film with love. (Though, of course, those are necessary ingredients to the best romantic comedies.) For the most part, rom-coms have a “meet cute” where the leads meet in an unconventional way. (Take You’ve Got Mail, for example, where Meg Ryan and Tom Hanks’ characters meet online, unaware that they hate each other in real life.) Of course, not all of the best romantic comedies start with the meet cute. (Crazy Rich Asians is a good example of a rom-com that starts in the middle of a serious relationship.) But for the most part, meet-cutes—as well as the grand finale kiss—are expectations that viewers have of the best romantic comedies.
So if you’re in the mood for some love and laughs, check out our list of the best romantic comedies ahead and embark on your next rom-com binge.
A version of this post was originally published in July 2020.
Our mission at STYLECASTER is to bring style to the people, and we only feature products we think you’ll love as much as we do. Please note that if you purchase something by clicking on a link within this story, we may receive a small commission of the sale.
He’s Just Not That into You (2009)
Based on the 2004 book by two former Sex and the City screenwriters, He’s Just Not That into You follows five different couples at different stages of their relationship. The star-studded cast includes Jennifer Aniston, Ben Affleck, Drew Barrymore, Bradley Cooper and Scarlett Johansson as singles and marrieds who, plain and simple, have issues in their relationships.
Palm Springs (2020)
Palm Springs, which premiered Hulu, stars Andy Samberg and Cristina Milioti as two wedding guests who become stuck in a Ground Hog’s Day-like time loop. Milloti plays Sarah, the sister of the bride, while Samberg plays Nyles, the boyfriend of one of the bridesmaids. The film follows Sarah and Nyles as they try to find a way to escape the time loop—and fall in love in the process.
Crazy Rich Asians (2018)
Crazy Rich Asians, based on Kevin Kwan’s novel of the same title, was one of the best romantic comedies of 2018. The film stars Constance Wu as a Chinese-American woman named Rachel who travels to Singapore for her boyfriend’s best friend’s wedding. Little does Rachel know, her boyfriend, Nick Young, is a member of one of the wealthiest families in Singapore and has a mother who disapproves of almost anyone he dates, especially an American.
27 Dresses (2008)
27 Dresses stars Katherine Heigl as Jane, a woman who’s been the maid-of-honor in 27 weddings but has never been a bride herself. At a wedding, Jane meets a handsome writer named Kevin, who covers weddings for a local newspaper, but in reality, hates them. As the two spend more time together for Jane’s sister Tess’ wedding, Jane and Kevin find they have more in common than they think.
How to Lose a Guy in 10 Days (2003)
How to Lose a Guy in 10 Days is regarded as one of the best romantic comedies of the 2000s. The film stars Kate Hudson as a women’s magazine writer named Andie who is assigned a story to write about how she can make a man break up with her in 10 days or less. On the flip side, the man she’s trying to woo and un-woo, Benjamin, makes a bet with his friends that he can make a woman tell him she loves him in the same amount of time.
When Harry Met Sally (1989)
When we think of the best romantic comedies, When Harry Met Sally always comes to mind. The film stars Meg Ryan and Billy Crystal as two people who meet via chance encounters for 12 years. The film, which is remembered for the iconic Katz Deli orgasm scene, raises the question if men and women can ever just be friends.
Sleepless in Seattle (1993)
Meg Ryan ruled the ’90s rom-coms, so it’s no surprise that three of her movies are on this list of the best romantic comedies. Sleepless in Seattle stars Tom Hanks as Sam, a single father to a 8-year-old son who lost his wife to cancer. One day, Sam’s son calls a local radio station and persuades his father to tell his story on the radio. The story wins over the hearts of hundreds of listeners, including Annie (Ryan), who decides whether or not to reach out to him.
You’ve Got Mail (1998)
After Sleepless in Seattle, Hanks and Ryan returned with another best romantic comedy, You’ve Got Mail. The film stars Hanks as Joe, a the executive of a mega bookstore chain that tries to run out an independent bookstore owned by Kathleen (Ryan.) The two hate each other in real life, but unbeknownst to them, they’ve been chatting anonymously with each other online and start to develop feelings for one another. You can only imagine what happens when they meet each other in real life.
How Stella Got Her Groove Back (1998)
How Stella Got Her Groove Back, based on Terry McMillan’s novel of the same title, stars Angela Basset as Stella, a 40-year-old stockbroker, who’s persuaded to go on a vacation to Jamaica with her best friend. On vacation, Stella meets a handsome islander named Winston Shakespeare, who’s 20 years younger than her. Their meet cute turns into a blossoming romance.
Always Be My Maybe (2019)
Always Be My Maybe, which was released on Netflix, stars Ali Wong as Sasha, a celebrity chef who reunites with her childhood best friend Marcus (Randall Park) after a visit back home to San Francisco. The film, which was written by Wong and Park, follows the characters as they reconnect and confess their feelings for each other from childhood.
Something’s Gotta Give (2003)
Something’s Gotta Give is often seen as one of the best romantic comedies for its storyline between two leads over 50 years old. The film, written by Nancy Meyers, stars Jack Nicholson as Harry, a 60-something playboy, and Diane Keaton, a successful Broadway playwright, who fall in love with each other despite being complete opposites.
Rumor Has It (2005)
Jennifer Aniston was the rom-com queen of the 2000s, so of course one of her films would make the list of the best romantic comedies. Rumor Has It stars Aniston as Sarah, a writer in New York City, who travels to her home in California for her younger sister’s wedding. At home, she learns information about her grandmother that leads to questions about who her real father is.
Bridget Jones’s Diary (2001)
Renée Zellweger was nominated for an Oscar for her role as Bridget in Bridget Jones’s Diary, which follows a 32-year-old single woman in London who writes a diary about what she wishes she could chnage about her life. That all changes when two men—played by Colin Firth and Hugh Grant—vie for her affection. The film is a reinterpretation of Jane Austin’s Pride and Prejudice.
Love, Actually (2003)
Love, Actually may be a holiday movie, but it’s seen as one of the best romantic comedies year-round. The film, which stars several well-known British actors such as Keira Knightley and Hugh Grant, is set in London and follows 10 different stories about various individuals and their love lives. The film starts five weeks before Christmas and continues in a weekly countdown until the holiday arrives.
Maid in Manhattan (2002)
Jennifer Lopez was also a rom-com queen of the 2000s. In Maid in Manhattan, she stars as Marisa, a hotel maid and a single mother, who falls in love with a high-profile politician who rents a room in her hotel. After its release the film went on to gross more than $100 million past its budget.
Four Weddings and a Funeral (1994)
Four Weddings and a Funeral, which was remade into a TV series on Hulu in 2019, follows a circle of friends on a numbner of social occasions as they each find romance. The film’s cast include Andie MacDowell, Hugh Grant and Kristin Scott Thomas.
Deliver Us From Eva (2003)
Deliver Us from Eva stars LL Cool J as Ray, a man who’s paid to date a woman named Eva, played by Gabrielle Union. The film is considered a modern remake on William Shakespeare’s play The Taming of the Shrew.
Notting Hill (1999)
Notting Hill stars Hugh Grant as a London book seller who meets a famous American actress played by Julia Roberts after she happens to walk into his shop. Over the course of the film, Grant’s character navigates what it means to date an A-list actress. The film also won a BAFTA after its release in 1999.
Sweet Home Alabama (2002)
Sweet Home Alabama stars Reese Witherspoon as a young woman who’s reinvented herself as a New York City socialite and returns home to Alabama to finalize her divorce form her husband after they’ve been separated for seven years. As they sort out their divorce, the two fall back in love with each other.
50 First Dates (2004)
50 First Dates stars Adam Sandler as a man named Harry, a marine veterinarian, who meets and falls for an art teacher named Lucy. After learning that she has anterograde amnesia, he makes a promise to win her over each day.
The Proposal (2009)
The Proposal stars Sandra Bullock as Margaret, a chief editor at a New York City book publisher who forces her American assistant, played by Ryan Reynolds, to marry her so she avoid being deported back to her home country in Canada. What starts as a rocky relationship soon becomes romantic as Margaret and her assistant, Andrew, learn more about each other.
13 Going on 30 (2004)
My Big Fat Greek Wedding (2002)
My Big Fat Greek Wedding, which was nominated for an Oscar at the 75th Academy Awards, stars Nia Vardalos as Fotoula “Toula” Portokalos, a Greek-American woman who, to the dismay of her family, falls in love with a non-greek man named Ian Mller (played by John Corbett.)
The Best Man (1999)
The Best Man stars Taye Diggs as Harper, a bestselling writer and a bachelor, who tries to hide the fact that his new book is based on the love lives of his group of friends. Harper is also the best man to his best friend Lance’s wedding. Trouble comes when an advance copy of his book finds itself in the hands of his ex Jordan, played by Nia Long.
In Hitch, Will Smith stars as Alex “Hitch” Hitchens, a dating coach whose knowledge about relationship fails him when he’s rejected by Sara Melas (played by Eva Mendes), a reporter who digs for dirt on one of Hitch’s clients.
Monster in Law stars Jennifer Lopez as Charlotte, a woman in a whirlwind relationship with Dr. Kevin Fields, played by Michael Vartan. The issue, however, is when Kevin proposes to Charlotte soon after they start dating, Charlotte doesn’t realize how disapproving Kevin’s mom, Viola, played by Jane Fonda, would be about their new relationship.