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The 12 best romantic comedies of all time

From Moonstruck to Sideways, these are the romantic comedies to stream now

Cher and Nicolas Cage in Moonstruck
MGM

Whether you’re having a great day or a terrible one, a wonderful comedy can make your day. Comedies are designed to be pick-me-ups so I’m not exactly saying anything new. The romantic comedy, though, is a particular subgenre that can be transcendent when it’s great.

The best romantic comedy movies are not for everyone, and that’s OK. If you’d rather watch an action movie or a sci-fi movie, nobody blames you. For those of you here to escape into a world of romance and love, look no further, as we have compiled a list of the best romantic comedies of all time for your viewing and streaming pleasure.

Serendipity (2001)

Serendipity
90m
Genre
Comedy, Romance, Drama
Stars
John Cusack, Kate Beckinsale, Jeremy Piven
Directed by
Peter Chelsom
Watch on Amazon
One of the more underrated films on our list today, Serendipity is a sweet story about fate and trust, and what some people will do to test it. When quick-witted Jonathan Trager (John Cusack) meets the lovely Sara Thomas (Kate Beckinsale) while Christmas shopping, it immediately seems that the universe has brought them together. Being so infatuated with destiny, they decide to test its limits and see if it will bring them back together again in the future, waiting 10 long years before they both decide to begin searching for one another. With a firm belief that “everything happens for a reason,” this film will charm and impress with its ridiculous love escapades and a hilarious appearance from Eugene Levy.

Moonstruck (1987)

Moonstruck
102m
Genre
Comedy, Drama, Romance
Stars
Cher, Nicolas Cage, Vincent Gardenia
Directed by
Norman Jewison
Watch on Apple TV+
In an unusual role and one of the best Nicolas Cage movies, this romantic comedy is a story about confusion, love, and rediscovering what it means to be alive. An Italian-American widow named Loretta (Cher) falls in love with the younger brother of her fiancé, beginning a hilarious and enchanting tale about how the moon and the stars can bring people together against all odds. Unexpectedly, the chemistry between Cher and Cage is palpable in this film as their romance blossoms on-screen, cementing Cher as a gorgeous icon and transforming Cage into a sudden and unlikely dreamboat.

When Harry Met Sally... (1989)

When Harry Met Sally...
96m
Genre
Comedy, Romance, Drama
Stars
Billy Crystal, Meg Ryan, Carrie Fisher
Directed by
Rob Reiner
Watch on Amazon
A hilarious romantic comedy, When Harry Met Sally is one of the first movies you’ll hear about if you research the genre. The film follows two recent college graduates and friends, Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan), who drive together to New York from Chicago and talk about the difficulties of platonic friendships. 10 years later (seems to be a theme), they meet again in a coffee shop where their alternating theories on the subject begin to be tested along with their friendship. Think you don’t like romantic comedies? Try this one out. You’ll be cackling at the brilliantly written and perfectly executed jokes and situations that may hit a little too close to home for some.
When Harry Met Sally... Official Trailer #1 - Billy Crystal Movie (1989) HD

Say Anything... (1989)

Say Anything...
100m
Genre
Romance, Comedy, Drama
Stars
John Cusack, Ione Skye, John Mahoney
Directed by
Cameron Crowe
Watch on Amazon
In a somewhat corny yet wholly ’80s fashion, Say Anything is the romantic comedy that defines a generation of romantics with quirky magnificence. A straight-A, bound-for-success high school student (Ione Sky) becomes distracted by the head-over-heels antics of Lloyd (John Cusack), a notorious, kickboxing underachiever who doesn’t know what he wants until he finds love. Wonderfully acted, Cusack really steals the spotlight in this film as the lover boy unapproved by the controlling father. And of course, he blasts the Peter Gabriel classic “In Your Eyes” from a boombox outside her window.
Say Anything... (1989) Trailer #1 | Movieclips Classic Trailers

Bull Durham (1988)

Bull Durham
108m
Genre
Comedy, Romance
Stars
Kevin Costner, Susan Sarandon, Tim Robbins
Directed by
Ron Shelton
Watch on Apple TV+
A Kevin Costner classic, Bull Durham follows players in the minor leagues as they show us that there is more to baseball than just baseball, especially when your team has a devoted, annual groupie. With fantastic performances from Costner, Susan Sarandon, and Tim Robbins, we take part in a romantic comedy following a love affair that, in the major leagues, would have gained much more attention from the fans. Focusing more on love and romance than the actual sport they’re playing, this film is still considered to be one of the best baseball movies ever made.

Groundhog Day (1993)

Groundhog Day
101m
Genre
Romance, Fantasy, Drama, Comedy
Stars
Bill Murray, Andie MacDowell, Chris Elliott
Directed by
Harold Ramis
Watch on Netflix
More of an endlessly entertaining comedy that turns romantic, Groundhog Day is arguably the best Bill Murray film in history, making it a film you can watch over and over and over again like there’s no tomorrow. When a brash and disillusioned TV weatherman travels to Punxatawney to cover the annual Groundhog Day ceremony, he finds himself trapped and reliving the same day over and over again, unable to discover why or how. Masterfully performed by our star, we get to witness Murray’s character going through all 5 stages of grief as he starts to uncover the truth about his situation and how he might escape it.

The Princess Bride (1987)

The Princess Bride
99m
Genre
Adventure, Family, Fantasy, Comedy, Romance
Stars
Cary Elwes, Robin Wright, Mandy Patinkin
Directed by
Rob Reiner
Watch on Disney+
A witty fairytale about love, adventure, and hope, The Princess Bride is another timeless classic on our list today that nobody will judge you for watching a few dozen times. When a boy is sick in his bed, his grandfather decides to read him the story of The Princess Bride, mostly for the good quality of the incredible tale (not to mention Peter Falk’s legendary narration), but also to reconnect with his growing grandson. Cleverly written and full of excellent cameos, this film is a good choice for almost any occasion.
The Princess Bride Official Trailer #2 - Wallace Shawn Movie (1987) HD

The Big Sick (2017)

The Big Sick
120m
Genre
Comedy, Drama, Romance
Stars
Kumail Nanjiani, Zoe Kazan, Holly Hunter
Directed by
Michael Showalter
Watch on Amazon
The Big Sick is based on the real-life love story of comedian Kumail Nanjiani and Emily V. Gordon. The story follows Nanjiani as he struggles to build up a career in stand-up. After a run-in with a heckler named Emily (Zoe Kazan), a relationship quickly forms. However, the couple is faced with a family pushback and when they break up, Emily slips into a coma that ultimately brings them back together. This original dramedy is one of the best Prime movies Amazon has to offer.
The Big Sick Trailer #1 (2017) | Movieclips Trailers

10 Things I Hate About You (1999)

10 Things I Hate About You
97m
Genre
Comedy, Romance, Drama
Stars
Julia Stiles, Heath Ledger, Joseph Gordon-Levitt
Directed by
Gil Junger
Watch on Disney+
With a story based on Shakespeare’s The Taming of the Shrew and re-vamped to fit the 90s grunge of Seattle, 10 Things I Hate About You is a timeless classic, giving high-school rom-coms a run for their money. In an upper-middle-class Seattle high school, Bianca (Larisa Oleynik) is a popular and beautiful girl that many would feel lucky to date (arrogant schmucks and romantic nerds alike), but with her terrified and controlling father, she is not allowed to date unless her blunt and abrasive older sister, Kat (Julia Stiles) decides to date somebody. Starring a wide array of recognizable faces and featuring some excellent, witty dialogue, you’re likely to fall victim to Heath Ledger’s endlessly charming smile.
10 Things I Hate About You -Official Trailer #1 (1999) Heath Ledger Movie

(500) Days of Summer (2009)

(500) Days of Summer
95m
Genre
Comedy, Drama, Romance
Stars
Joseph Gordon-Levitt, Zooey Deschanel, Geoffrey Arend
Directed by
Marc Webb
Watch on Hulu
A tale of self-discovery and reflection, (500) Days of Summer is a quirky romantic comedy that explores the path to true love and the difficult yet realistic obstacles that lay along the way. A hopelessly romantic greeting card writer, Tom (Joseph Gordon-Levitt) falls in love with a co-worker (Zooey Deschanel) who doesn’t believe in love. Offbeat and somehow also whimsical, this film will be relatable on some level or another as these two young hearts try to figure out the way of the world as well as each other.

Forgetting Sarah Marshall (2008)

Forgetting Sarah Marshall
111m
Genre
Comedy, Romance, Drama
Stars
Jason Segel, Kristen Bell, Mila Kunis
Directed by
Nicholas Stoller
Watch on Amazon
Judd Apatow is known for his dominance in comedy in the late 2000s, but it’s this Apatow produced comedy that may actually be the era’s crowning achievement. Starring Jason Segel as a man who travels to Hawaii to forget about his ex, only to discover that his ex and her new boyfriend are there as well, the movie is filled with both comedy stars of the future and amazing punchlines. On top of all that, though, it’s a tender, sweet story about a man trying to grapple with a huge change in his life and finding love in one of the most beautiful places on earth.
Forgetting Sarah Marshall Official Trailer #1 - Jason Segel, Mila Kunis Movie (2008) HD

Sideways (2004)

Sideways
127m
Genre
Comedy, Drama, Romance
Stars
Paul Giamatti, Thomas Haden Church, Virginia Madsen
Directed by
Alexander Payne
Watch on Amazon
Sideways involves a road trip and two middle-aged men and was not supposed to involve romance, but this romantic comedy, as you might guess, revolves around unexpected romance. Miles (Paul Giamatti), a depressed and unsuccessful writer with a passion for wine, takes his soon-to-be-married friend Jack (Thomas Haden Church) on a trip to California wine country. Jack, an actor past his prime, is looking for a final fling before settling down. Their agendas clash as Miles seeks a relaxing exploration of wineries, while Jack pursues women. Both men encounter women who complicate their plans. Miles connects with a fellow wine enthusiast, Maya (Virginia Madsen), while Jack deceives a waitress named Stephanie (Sandra Oh) about his upcoming marriage. Sideways won an Oscar and is known for its sharp dialogue, memorable characters, and exploration of complex emotions.
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Joe Allen
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Joe Allen is a freelance culture writer based in upstate New York. His work has been published in The Washington Post, The…
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