50 Best Romantic Comedies (And Where to Stream Them)

When a loved one dies, especially a spouse, it often triggers a journey to explore a new life. For Chicago architect Sam Baldwin and his son, that journey begins with a move to Seattle. Though Sam isn’t in a rush to find love again, his son, Jonah, wants more for his father and pushes his father to talk about their loss on a radio show. It starts a whole new chapter in Sam’s life, one that includes Annie Reed, a reporter that feels incomplete in her engagement.

Though Tom Hanks and Meg Ryan spend most of the movie separated, Nora Ephron’s writing creates a bond between the two that few romantic comedies are able to. It’s a great movie for those looking for a push to put themselves back out there and an inspiration for those lost in grief.

You can stream Sleepless in Seattle with a Showtime Channel subscription free trial on Amazon or Hulu, or rent it on Amazon.

All C. C. Baxter wanted to do was rise in the ranks of the corporate ladder. Unfortunately, he took the strange way out by letting executives use his apartment for their extramarital affairs. While it complicates his life a bit, it does give him the chance to finally approach Fran Kubelik, an elevator operator he’s fancied.

Jack Lemon and Shirley MacLaine shine in this promiscuous comedy that is definitely for a more adult crowd. The Apartment isn’t your typical shallow rom-com, so expect a deeper, more emotional experience when you sit down with this classic.

You can stream The Apartment on Amazon Prime Video right now.

It was a chance encounter that bookstore owner William Thacker never could have expected. When the world’s most beloved actress walked into his store, it began an unexpected friendship that soon blossomed into something so much more. However, dating a star isn’t easy, especially one as beautiful and sought after as Anna, and William finds himself struggling with the drama that comes with dating the starlet. 

Hugh Grant’s portrayal as the unassuming bookstore owner perfectly contrasts Julia Roberts’ movie star persona. Notting Hill earned praise by the BAFTA and the British Comedy Award and was the highest-grossing British film of 1999.

You can watch Notting Hill with an HBO Channel subscription via Prime Video, or you can rent it here.

Zooey Deschanel and Joseph Gordon-Levitt perfectly portray Summer Finn and Tom Hansen in this poignant story about love. 500 Days of Summer isn’t the romantic comedy you expect, where the couple goes through trials and tribulations and wind up together. In fact, it begins after the romance has ended and the two have parted ways.

Throughout the film, viewers get to watch the strange relationship between Tom and Summer run its course in a nonlinear structure. It’s a tale that many may relate to as Tom is left to decide whether to listen to his closest friends and little sister or continue on the complicated path with Summer, a girl who doesn’t even believe in true love.

You can stream 500 Days of Summer with a Starz Channel 30-day trial via Prime Video or Hulu+.

Put Jack Nicholson and Diane Keaton in front of the camera together, and you’re guaranteed gold. That’s exactly what director Nancy Meyers got during the filming of Something’s Gotta Give. 

Harry Sanborn may have an affinity for younger women, but accomplished Broadway playwright Erica Barry may get him to drop old habits. Something’s Gotta Give features an incredible ensemble cast, including Keanu Reeves, Amanda Peet, Frances McDormand, Jon Favreau, and Paul Michael Glaser. There is really no wonder why the film (and Diane Keaton) walked away with 12 award nominations and three wins.

You can stream Something’s Gotta Give right now on Amazon Prime VIdeo for free (with ads) or rent it to stream without ads.

A journey for love becomes a woman’s quest for self-discovery when she realizes a personal ad that caught her interest was for another woman. After a lifetime of a disappointing love life, Jessica Stein finds herself looking to Helen Cooper, an art gallery employee who’s looking for the cure for unfulfilling romances. 

Kissing Jessica Stein features Jennifer Westfeldt and Heather Juergensen as the two women caught in an endless loop of bad relationships. They work well together to form the awkward but passionate relationship between Jessica and Helen and deliver on an independent rom-com that stands up to the AAA classics.

You can stream Kissing Jessica Stein on Prime Video right now.

After suffering yet another break-up, former club DJ and record store owner Rob Gordon explores his past relationships to see where he went wrong. As he makes a list of his top five breakups, Rob starts to realize where he went wrong and sets out to save his recently-ended relationships.

High Fidelity was adapted from Nick Hornby’s 1995 novel and uses music and the characters’ knowledge for the industry to tell its story of redemption and self-discovery. John Cusack stars as Rob alongside Iben Hjejle, Jack Black, Todd Louiso, and Catherine Zeta-Jones.

(Not to be confused with the new High Fidelity series on Hulu).

You can rent and stream the High Fidelity movie on Prime Video.

Adapted from Shakespeare’s 16th-century piece, Much Ado About Nothing follows two young lovers as they try to get two unlikely people to marry. With time to pass before their wedding, Hero and Claudio work with Don Pedro to work on a “lover’s trap.” Their targets? Conceited bachelor Benedick and Beatrice, a sparring partner. When Don Jon steps in to try and break up Hero and Claudio, the situation gets quite a bit more complicated.

The multi-award nominated film brings together an impressive cast of Kenneth Branagh, Emma Thompson, Robert Sean Leonard, Kate Beckinsale, Denzel Washington, and Keanu Reeves to modernize Shakespeare’s comedy.

What happens when two television reporters who are pretty full of themselves try to vie for the attention of their network’s news producer? Throw in some organizational changes and you have a recipe for chaos – and a memorable romantic comedy. The complicated love triangle can have no real happy ending, but it’s the journey to the resolution that really sells this unique story

The film earned seven Academy Award nominations, five Golden Globe Awards, and landed on AFI’s 100 Years… 100 Movies list in 2000. William Hurt, Albert Brooks, and Holly Hunter depict the awkward love triangle in this James L. Brooks comedy classic.

You can rent Broadcast News on Amazon Prime Video right now.

Kevin Kwan’s 2013 novel, Crazy Rich Asians, shined the spotlight on the Asian elite. The movie makes few changes as it focuses on the same concept of Asian life. When Rachel Chu follows her boyfriend, Nick, to Singapore for a wedding, she quickly learns that her beau is not only rich, he’s a commodity. Rachel struggles to fit in with Nick and his family as she learns more and more about the man she loves.

Crazy Rich Asians earned more than 25 award nominations and took home eight. Its cast includes names like Constance Wu, Henry Golding, Awkwafina, and Ken Jeong.

It’s available to stream on Prime Video with a Cinemax trial or if you rent it.

It’s not easy to find love when you’re the President of the United States, but that didn’t stop President Andrew Shepherd from wanting to pursue a relationship with a lobbyist. Sydney Ellen Wade may be new to Washington, D.C., but Shepherd already has his eye on her.

While dealing with the usual business of a president, Shepherd tries to win the affection of Wade. His busy schedule and conflict of interests make it difficult, but the widowed president isn’t one to back down easily. 

The American President stars Michael Douglas and Anette Bening and earned several nominations, including an Academy Award five Golden Globes.

Who can forget that nose? Even if you’ve never seen Roxanne, it’s a difficult feature of Steve Martin’s character to not know about. It’s so prominent that C. D. Bales suffers from a complex that keeps him from fully enjoying life. However, when a handsome fireman named Chris attracts the attention of Roxanne, Bales steps in to help the two get together.

Using his love for Roxanne, Bales writes letters from Chris and creates the image of the perfect man. However, with Chris’ personality vastly different from what’s presented in the letters, it’s a plan that is destined to fail.

Roxanne is a retelling of the 1897 verse play, Cyrano de Bergerac by Edmon Rostand. Steve Martin adapted the play and is joined by Daryl Hannah, Shelley Duvall, and Fred Willard.

You can rent or buy Roxanne right on Prime Video right now.

Alfred Kralik and Klara Novak may not like each other, but they’re both in for a big surprise. The two have been pen pals for some time and Alfred has developed feelings for how Klara is on paper. Adapted from the 1937 Hungarian play Parfumerie, The Shop Around the Corner presents a dilemma for the two as they grow more in love on paper.

Ernst Lubitsch’s film is an acclaimed romantic comedy with a place on AFI’s 100 Years… 100 Passions list. It was even preserved in the United States National Film Registry of the Library of Congress for being “culturally, historically, or aesthetically significant.”

Jimmy Stewart and Margaret Sullavan deliver stellar performances in this movie about unlikely lovers.

You can rent and stream this classic romantic comedy on Prime Video.

Inspiration to become a better person can come from anywhere. As About a Boy proves, even a 12-year-old boy can remind us of the importance of straightening up our lives and leaving behind the slacker lifestyle.

When Will Freeman meets young Marcus Brewer, he’s spent much of his life living off royalties he didn’t earn. Wanting to find a suitable person for his depressed single mother, Marcus takes it upon himself to teach Will how to grow up and act his age. The movie stars a young Nicholas Hoult alongside Hugh Grant, Toni Colette, and Rachel Weisz. It’s this great cast that helped earn the film five award nominations.

About a Boy is available to stream with a 7-day Starz channel add-on trial via Prime Video or you can rent it.

Breakups are hard. They’re made even harder when you wind up staying in the same tropical resort as your ex and their new beau. All Peter Bretter wanted to do was get away, but his Hawaiian vacation is complicated by the presence of his former love, star actress Sarah Marshall, and the rock star boyfriend she cheated on him with. As he works through his myriad of emotions, Peter gets close to hotel employee Rachel Jansen, which further muddles the situation.

Forgetting Sarah Marshall stars Jason Segel, Kristen Bell, Mila Kunis, and Russell Bandt, who deliver standout performances to convey the awkwardness of their situation.

You can stream Forgetting Sarah Marshall on Prime Video right now.

You don’t earn six Oscar nominations and a total of 19 nominations for a variety of other ceremonies without being good. In fact, for Some Like It Hot, “good” is a vast understatement. 

It’s not easy for men to blend in perfectly with an all-female band, but that’s exactly what Joe and Jerry did after witnessing a massacre. Hoping to evade Spats Colombo, the mobster responsible for the killings, the two try to leave town but find that the way out isn’t easy, especially when they start to form real relationships.

Marilyn Monroe, Tony Curtis, and Jack Lemmon deliver a riotous good time, which earned critical praise upon its release. In 1972, a musical based on the film opened on Broadway. Rumors of an updated version returning to the stage started to circulate in 2019.

You can stream Some Like it Hot with an Amazon Prime subscription.

What luck would a reporter need to have in order to aimlessly run into an heiress trying to run away from her family? When he realizes what Ellen “Ellie” Andrews is up to, Peter Warne blackmails her to stay at his side until she’s returned to her new husband, King Westley. What starts as a forced companionship turns into something so much more as they continue their journey back to King. 

It Happened One Night is among one of the first “screwball comedies,” or a genre of comedy that often deals with differing classes. Clark Gable’s Peter is a far cry from Claudette Colbert’s heiress and the class difference is evident throughout the film. 

At the 1934 Academy Awards, it Happened One Night took home five awards, including Best Picture, Best Director, Best Actor, Best Actress, and Best Writing, Adaptation.

You know the song, but have you seen the movie Deep Blue Something tries to use to salvage a failing relationship? If not, you’re missing out on an Audrey Hepburn classic. Holly Golightly is a New York City socialite who takes a liking to a newcomer to her building. However, Holly’s attraction to money keeps getting in the way of her relationship with Paul.

Hepburn received ample praise for her portrayal of Golightly and even earned her an Oscar nomination for Best Actress in a Leading Role. The film was also responsible for the popular Henry Mancini and Johnny Mercer song, “Moon River,” which also received an Oscar nomination.

You can rent and stream Breakfast at Tiffany’s on Prime Video.

Hepburn may not have won the Oscar nomination for her portrayal of Holly Golightly in Breakfast at Tiffany’s, but her performance as Princess Ann in Roman Holiday certainly did the trick. Alongside Gregory Peck, Hepburn delivers a memorable performance in this romantic comedy about a sheltered princess that wants to see Rome on her own. Along the way, she meets American reporter Joe Bradley, which sparks a brief romance that’s destined not to last.

Roman Holiday went on to earn 11 award nominations, including nine Academy Awards and four BAFTA Awards. It took home three Oscars, specifically for Best Actress, Best Costume Design, and Writing.

Roman Holiday is available to stream on Prime Video with a Prime membership.

Some romantic comedies are about more than just two people falling in love. For Love, Simon, it’s about the journey that Simon Spier must go on once the secret of his sexual orientation comes to light. 

Nick Robinson plays the conflicted titular character, who enjoys an online relationship with a mysterious boy named Blue. While he enjoys Blue’s digital company, Simon struggles with the world in front of him, especially when his family learns of his secret. Love, Simon is a generationally appropriate coming-of-age story adapted from Becky Albertalli’s novel Simon vs. the Homo Sapiens Agenda.

Edward Lewis isn’t big on relationships, but when he’s faced with attending a series of social events, he’d rather not do so alone. For his date, he chooses Vivian Ward, a Hollywood prostitute with a severe lack of manners. The two find a common bond, however, and start to form an unexpected relationship.

Based on Roy Orbison’s “Oh, Pretty Woman,” Garry Marshall’s vision of J. F. Lawton’s screenplay follows two unlikely lovers as they discover their differing worlds make them perfect for each other. Originally, Pretty Woman was intended to be quite a bit darker, but the shift to a romantic comedy proved fruitful.

The Julia Roberts classic Pretty Woman is now available to rent or buy and stream on Prime Video.

It’s not easy being pretty and rich. Just ask Cher, who gets her first taste of real life in this coming-of-age teen rom-com. Alicia Silverstone delivers one of her most notable performances as the rich Beverly Hills high school student. Joined by her closest friends and the school’s newest student, Tai Frasier, Cher comes face-to-face with the worst parts of growing up. 

Stacey Dash, Brittany Murphy, Paul Rudd, Dan Hedaya, Breckin Meyer, Donald Faison, and Justin Walker round out an impressively talented class that embodies Beverly Hills and the swanky fashion of the 90s. Clueless is the quintessential high school romantic comedy that spawned a stage musical, a series of books and comics, and a spin-off TV series.

You can stream Clueless by renting it on Prime Video.

Nicholas Cage delivers one of his most memorable performances as a one-handed butcher who accidentally falls in love with his brother’s fiance. After Loretta Castorini’s husband passes away, she accepts the proposal of her boyfriend, Johnny Cammareri. In his absence, though, Loretta becomes close to Johnny’s brother, Ronny. 

It may be a complicated situation, but it makes for great entertainment. Especially with talent like Cher and Cage stepping in as the overdramatic pairing. Moonstruck certainly struck a chord with critics and even scoring more than 35 award nominations and 18 wins, including three Academy Awards.

You can stream Moonstruck right now with an Amazon Prime subscription.

Not to be confused with the Philadelphia Experiment, an alleged Navy experiment said to have resulted in a destroyer escort being teleported to another dimension, The Philadelphia Story follows a socialite just before her wedding day. While her nuptials were expected to go off without a hitch, the arrival of her ex-husband and a tabloid journalist complicate things quite a bit.

Cary Grant plays the charming C. K. Dexter Haven, who shows up for Tracy Samantha Lord’s (Katharine Hepburn) with plans of his own. The Philadelphia Story explores Lord’s intricate love life as she slowly starts to come to terms with who she really is.

The Philadelphia Story is available to rent to stream on Prime Video.

Wanting to escape the marriage arranged for him, Prince Akeem of Zamunda travels to the United States for his 21st birthday. There, he hopes to find true love and a woman that he chooses to marry. When he arrives in the states, though, he finds difficulty integrating into their different cultures. 

Created by Eddie Murphy, Coming to America became a quotable classic that’s remembered for Murphy’s iconic role. He and Arsenio Hall provided the talent for eight total characters and were joined by James Earl Jones, John Amos, Louie Anderson, Madge Sinclair, and even a brief cameo by Samuel L. Jackson. 

 After many years of anticipation, a sequel was finally officially announced in January 2019.

Meanwhile, you can catch the original streaming on Prime Video.

When a grandfather sits down to read his grandson a tale of adventure, viewers join them on an incredible journey of love and redemption. A farm boy turned pirate embarks on a grand adventure, battling through deadly obstacles in order to reunite with his long lost love. Unfortunately, some perils are more cunning than others.

The Princess Bride is the fairytale romance that isn’t afraid to bend the rules a bit to cater to a broader audience. It’s a whimsical tale of pirates and warlocks and damsels in distress, featuring an unlikely hero and his duo of miscreants.

The Princess Bride is available to rent on Prime Video right now.

Sometimes, love takes a while to blossom. For Harry and Sally, it certainly wasn’t love at first sight after the two first meet on a road trip from Chicago to New York. After a few chance encounters, though, a friendship blooms. When Harry Met Sally is more than your average rom-com. It’s a tale of discovery as the titular characters go years trying to find the right person to grow old with, unaware that they may have been there all along.

Rob Reiner crafted this classic comedy, which may leave you wondering if the person you should be with is already in your life. 

Sixteen Candles is an absolutely classic 80s romantic comedy that skyrocketed Molly Ringwald’s career, and made the world fall in love with Anthony Michael Hall, who played a loveable nerd in the film.

The film is about chasing the popular boy while trying to be someone you’re not to win him over, and it obviously is a theme that you’ll still find in high school classes nowaday; the movie holds up nicely.

You can stream Sixteen Candles on Prime Video right now.

If you’re looking for a great romantic comedy that goes off the beaten path, look no further than Juno. It’s a film about teenage love, and follows the story of Juno, who gets pregnant by a boy she likes in her high school. Of course, being a teenage mom-to-be has its social issues, but the story is filled with both heartfelt moments and off-brand humor – thanks to the comedy stylings of Michael Cera and Ellen Page.

Juno is definitely not your typical romcom, but it is a cult hit that’s one of my personal favorites.