The best romantic comedies of all time


Love and laughter go hand in hand, and there is nothing as refreshing as watching good love stories that make you laugh at the same time.

Are you looking for a classic romantic comedy or a new-age rom-com? Are you looking for a Ben Stiller, Adam Sandler, Seth Rogen, or an Eddie Murphy movie to make you laugh out loud and forget the moment or even a breakup? Well, look no further.

We all know there is love in sharing, so, we at the D360 central hub have scouted and compiled for you a list of the best romantic comedies of all time for you to watch and enjoy alone or with your loved ones.

Annie Hall

Year: 1977
Director: Woody Allen
Writers: Woody Allen, Marshall Brickman
Cast: Woody Allen, Tony Roberts, Diane Keaton, Carol Kane

Woody Allen’s Annie Hall is undoubtedly one of the best romantic comedies of all time! This critically acclaimed movie has won 3 Oscars, is regarded as one of the greatest movies of all time as well as holding the 28th position on Bravo’s “100 Funniest Movies”. Annie Hall is about an erratic New York comedian who falls in love with the ditsy Annie Hall.

Breakfast at Tiffany’s

Year: 1961
Director: Blake Edwards
Writers: Truman Capote, George Axelrod
Cast: Audrey Hepburn, George Peppard, Patricia Neal, Buddy Ebsen

Based on Truman Capote’s novel with the same name, Breakfast at Tiffany’s is Audrey Hepburn’s most memorable movie where she stars as a naïve and quirky socialite who falls in love with an aspiring writer who moves into her apartment, but there are some obstacles she has to deal with. This is a must-watch movie if you are looking for classic romantic comedy movies.

My Best Friend’s Wedding

Year: 1997
Director: P.J. Hogan
Writer: Ronald Bass
Cast: Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett

Julianne Potter, played by Julia Roberts, realises she is in love with her best friend after he tells her he is engaged and getting married to someone else and she has a few days to the wedding to get him for herself.
The soundtrack of this romantic comedy ‘I say a little prayer (for you)’, covered by Diana King was also a Billboard hot 100 hit.

There’s something about Mary

Year: 1998
Directors: Bobby Farrelly, Peter Farrelly
Writers: Ed Decter, John J. Strauss
Cast: Ben Stiller, Cameron Diaz, Matt Dillon, Lee Evans

This highly hilarious romantic comedy is positioned at number 27 on the list of the 100 funniest movies of the 20th century. It is about a man who met the girls of his dreams even though their first date was an epic failure. There’s something about Mary will definitely leave you in stitches.

When Harry met Sally

Year: 1989
Director: Rob Reiner
Writer: Nora Ephron
Cast: Meg Ryan, Billy Crystal, Carrie Fisher, Bruno Kirby

From the first time they met to numerous chance encounters in 12 years, excellent friends Harry and Sally debate on if sex can ruin a relationship between a man and a woman and are not close to getting an answer. Get ready to be wowed by a lot of explicit sexual humour as well stellar acting from the cast of this romantic comedy.

Knocked up

Year: 2007
Director: Judd Apatow
Writer: Judd Apatow
Cast: Seth Rogen, Katherine Heigl, Paul Rudd, Jonah Hill

Seth Rogen and Katherine Heigl are a perfect combination for this screamingly funny romantic comedy. Their brilliant interpretation of pregnancy after a one-night stand makes Knocked up one of the best romantic comedies you will ever watch.

Four Weddings and a funeral

Year: 1994
Director: Mike Newell
Writer: Richard Curtis
Cast: Hugh Grant, Andie MacDowell, James Fleet

This British romantic comedy circles around Charles, a committed bachelor, played by Hugh Grant and his friends through some social events and how they each encountered romance. Four Weddings and a funeral has won many awards, including Best Film and can’t be left out of the list of good romantic comedies.

The big sick

Year: 2017
Director: Michael Showalter
Writers: Emily V. Gordon, Kumail Nanjiani
Cast: Kumail Nanjiani, Zoe Kazan, Holly Hunter, Ray Romano

The big sick is a lovely romantic comedy about an interethnic couple and cultural differences they experience which is also based on a real-life story.

It follows Kumail, a Pakistani Uber driver and comic, who falls in love with Emily, an American girl. He is forced to meet her parents and make life-changing decisions after Emily falls mysteriously ill and is in a coma.


Year: 2005
Director: Andy Tennant
Writer: Kevin Bisch
Cast: Will Smith, Eva Mendes, Kevin James, Amber Valletta

What happens when a celebrity ‘date doctor’, renown for coaching men in the art of wooing women meets the woman of his dreams but can’t even start a dialogue with her in the first place? This Will Smith and Eva Mendes romantic comedy will leave you laughing till you fall off your seat.

50 first dates

Year: 2004
Director: Peter Segal
Writer: George Wing
Cast: Adam Sandler, Drew Barrymore, Rob Schneider, Sean Astin

If you are looking for the best romantic comedies, ’50 First dates’ is one of them. This comedy movie is about a man who is afraid of commitments until he meets the one woman he is actually happy to commit to. The only catch is that she suffers from short-term memory loss and has to woo her all over again after the first date.

Sweet Home Alabama

Year: 2002
Director: Andy Tennant
Writers: Douglas J. Eboch, C. Jay Cox
Cast: Reese Witherspoon, Patrick Dempsey, Josh Lucas

Melanie has a perfect life. She is a successful fashion designer, and the son of the Mayor of New York just proposed to her. Before she can walk down the aisle with her prince charming, there is only one teeny-weeny thing she has to do in Alabama… get divorced.

The Wedding Singer

Year: 1998
Director: Frank Coraci
Writer: Tim Herlihy
Cast: Adam Sandler, Drew Barrymore, Christine Taylor

The wedding singer is a funny, romantic comedy of the inevitable romance between an 80s wedding singer and a waitress who are both engaged to other people. This movie was a box office hit and it is claimed to be Adam Sandler’s best movie. Also, the chemistry between him and co-star, Drew Barrymore makes the wedding singer one of the best romantic comedy movies.

10 Things I Hate About You

Year: 1999
Director: Gil Junger
Writers: Karen McCullah, Kirsten Smith
Cast: Heath Ledger, Julia Stiles, Joseph Gordon-Levitt, Larry Miller

10 things I hate about you is a teen romantic comedy-drama that is a loose modern adaptation of Shakespeare’s ‘The taming of the shrew’. A high school teenager attempts to get the bad boy of their school to date his love interest’s sister to loosen her fathers.

Coming to America

Year: 1988
Director: John Landis
Writers: Eddie Murphy, David Sheffield
Cast: Eddie Murphy, Paul Bates, Garcelle Beauvais, Arsenio Hall

This classic movie is one of the best romantic comedies of all time! Yes, we said it! It stars Eddie Murphy, who plays Prince Hakeem, a lavish and pampered African prince who goes all the way to New York in search of true love while staying undercover. Coming to America was the highest earning film in 1988.

Pretty Woman

Year: 1990
Director: Garry Marshall
Writer: J.F. Lawton
Cast: Richard Gere, Julia Roberts, Jason Alexander

This is another movie high up in our romantic comedy movies list. Pretty woman is about Edward, a wealthy businessman who contracts a prostitute played by Julia Roberts to escort him on several social and business functions and ends up falling in love with her. Funny enough, this movie was meant to be a cautionary movie about class and sex work in Los Angeles but was reconsidered as a romantic comedy.

Lost in Translation

Year: 2003
Director: Sofia Coppola
Writer: Sofia Coppola
Cast: Bill Murray, Scarlett Johansson, Giovanni Ribisi, Anna Faris

Lost in translation is the story of an ageing actor who goes to Japan for a job and is a bit frustrated because he doesn’t understand the language. Things change when he bonds with a young female graduate.

Bridget Jones’s Diary

Year: 2001
Director: Sharon Maguire
Writers: Helen Fielding, Helen Fielding
Cast: Renée Zellweger, Colin Firth, Hugh Grant, Gemma Jones

This romantic comedy is based on Helen Fielding’s novel with the same name, which is an adaptation of Jane Austen’s Pride and prejudice and revolves around Bridget’s decision to keep a diary while improving her life and searching for love.

Roman Holiday

Year: 1953
Director: William Wyler
Writers: Ian McLellan Hunter, John Dighton
Cast: Gregory Peck, Audrey Hepburn, Eddie Albert

Roman holiday is a classic romantic comedy starring Audrey Hepburn, who plays the role of a bored princess who visits Rome and sneaks out of the embassy to explore the city and discovers love.

Groundhog Day

Year: 1993
Director: Harold Ramis
Writers: Danny Rubin (screenplay), Harold Ramis
Cast: Bill Murray, Andie MacDowell, Chris Elliott

A weatherman is assigned to cover the Groundhog Day event but realises he is caught up in a time loop and relieves the day over and over again. The situation only gets bearable after meeting Rita. A stage musical version of Groundhog Day was also premiered in 2016

How Stella got her groove back

Year: 1998
Director: Kevin Rodney Sullivan
Writers: Terry McMillan, Terry McMillan
Cast: Angela Bassett, Taye Diggs, Whoopi Goldberg, Regina King

How Stella got her groove back is another good comedy based on a novel with the same name by Terry McMillan. It revolves around a successful woman who is forced to take a vacation from her very structured life, and she goes to Jamaica and falls for a very young man.

Love Actually

Year: 2003
Director: Richard Curtis
Writer: Richard Curtis
Cast: Hugh Grant, Martine McCutcheon, Liam Neeson, Keira Knightley

This romantic comedy entails ten love series in one movie and is perfect for watching during the holiday season, as it is Christmas themed. This funny love movie was also a box office success


Year: 2011
Director: Paul Feig
Writers: Kristen Wiig, Annie Mumolo
Cast: Kristen Wiig, Maya Rudolph, Rose Byrne, Ellie Kemper

This hilarious chick-flick revolves around a group of bridesmaids, preparations for the main wedding and who is the bride’s best friend. ‘Bridesmaids’ was nominated for Golden Globe Award for Best Motion Picture – Musical or Comedy in 2011.

Crazy, Stupid, Love

Year: 2011
Directors: Glenn Ficarra, John Requa
Writer: Dan Fogelman
Cast: Steve Carell, Ryan Gosling, Julianne Moore, Emma Stone

This is one romantic comedy that will keep you laughing while Cal, a middle-aged man is asked for a divorce by his wife who cheated on him. He meets Jacob, a womaniser, who is happy to help Cal rediscover his manhood by picking up girls at bars.

Say Anything…

Year: 1989
Director: Cameron Crowe
Writer: Cameron Crowe
Cast: John Cusack, Ione Skye, John Mahoney

Say Anything… is one of those good romantic comedies that once you watch it, you will never forget it in a hurry. It was also positioned at number 11 on the list of the 50 best high-school movies by Entertainment Weekly in 2002.

Friends with Benefits

Year: 2011
Director: Will Gluck
Writers: Keith Merryman (screenplay), David A. Newman
Cast: Mila Kunis, Justin Timberlake, Patricia Clarkson, Jenna Elfman

This is a lovely romantic drama of two friends who decided to add sex to their relationship believing it will not complicate things and denying their new found feelings every time they are together. Stars Justin Timberlake and Mila Kunis great chemistry raised the bar on romantic comedy movies

Stuck in Love

Year: 2012
Director: Josh Boone
Writer: Josh Boone
Cast: Greg Kinnear, Jennifer Connelly, Lily Collins

What could possibly go wrong when a writer spies on his ex-wife and her new husband. He simply won’t focus on a new relationship as he is continuously moping about his ex-wife. Laugh along as you follow Bill and his family as they go through their relationship journey.


Year: 1995
Director: Amy Heckerling
Writer: Amy Heckerling
Cast: Alicia Silverstone, Stacey Dash, Brittany Murphy, Donald Faison

A wealthy, popular girl tries to boost a new student’s popularity without having any romantic issues. This high school romantic comedy is a cult movie and one of the most popular teen-flicks of the 1990s.

Wedding Crashers

Year: 2005
Director: David Dobkin
Writers: Steve Faber, Bob Fisher
Cast: Owen Wilson, Vince Vaughn, Rachel McAdams, Christopher Walken

Having the duo Owen Wilson and Vince Vaughn star together in this movie can only make it one of the best romantic comedies you can ever watch. Follow them as they gatecrash a wedding, preying on vulnerable women until one of them falls in love.

Silver Linings Playbook

Year: 2012
Director: David O. Russell
Writers: David O. Russell, Matthew Quick
Cast: Bradley Cooper, Jennifer Lawrence, Robert De Niro

Silver Linings Playbook is based on a novel by Matthew Quick with the same name and is about a bipolar teacher who gets out of an institution, moves back in with his parents, tries to reconcile with his ex-wife, then meets a lady with issues of her own.


Year: 2001
Director: Jean-Pierre Jeunet
Writers: Guillaume Laurant, Jean-Pierre Jeunet
Cast: Audrey Tautou, Mathieu Kassovitz, Rufus

Amélie is a French romantic comedy also known as Le Fabuleux Destin d’Amélie Poulain, and it centres on a trustful girl in Paris who makes up her mind to help others around her and discovers love along the way.