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The 11 best romantic comedies of all time

From Moonstruck to (500) Days of Summer, these are the best romantic comedies you can stream now

Cher and Nicolas Cage in Moonstruck

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, so 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)

Genre Comedy, Romance, Drama
Stars John Cusack, Kate Beckinsale, Jeremy Piven
Directed by Peter Chelsom
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-scapades and a hilarious appearance from Eugene Levy.

Moonstruck (1987)

Genre Comedy, Drama, Romance
Stars Cher, Nicolas Cage, Vincent Gardenia
Directed by Norman Jewison
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.
MOONSTRUCK (1987) | Official Trailer | MGM

When Harry Met Sally... (1989)

When Harry Met Sally...
Genre Comedy, Romance, Drama
Stars Billy Crystal, Meg Ryan, Carrie Fisher
Directed by Rob Reiner
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...
Genre Romance, Comedy, Drama
Stars John Cusack, Ione Skye, John Mahoney
Directed by Cameron Crowe
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
Genre Comedy, Romance
Stars Kevin Costner, Susan Sarandon, Tim Robbins
Directed by Ron Shelton
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.
Bull Durham Official Trailer #1 - Kevin Costner, Susan Sarandon Movie (1988) HD

Groundhog Day (1993)

Groundhog Day
Genre Romance, Fantasy, Drama, Comedy
Stars Bill Murray, Andie MacDowell, Chris Elliott
Directed by Harold Ramis
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
Genre Adventure, Family, Fantasy, Comedy, Romance
Stars Cary Elwes, Robin Wright, Mandy Patinkin
Directed by Rob Reiner
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
Genre Comedy, Drama, Romance
Stars Kumail Nanjiani, Zoe Kazan, Holly Hunter
Directed by Michael Showalter
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
Genre Comedy, Romance, Drama
Stars Julia Stiles, Heath Ledger, Joseph Gordon-Levitt
Directed by Gil Junger
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
Genre Comedy, Drama, Romance
Stars Joseph Gordon-Levitt, Zooey Deschanel, Chloë Grace Moretz
Directed by Marc Webb
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.
500 DAYS OF SUMMER | Official Trailer | FOX Searchlight

Forgetting Sarah Marshall (2008)

Forgetting Sarah Marshall
Genre Comedy, Romance, Drama
Stars Jason Segel, Kristen Bell, Mila Kunis
Directed by Nicholas Stoller
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

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Joe Allen
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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