The Best Romantic Comedies Of All Time Ranked

By Rick Gonzales | Published

Best Romantic Comedies of All Time

While we may not be in the 1990s heyday of romantic comedies, it is apparent that even today the romantic comedy has not died.  Audiences still believe in true love and still crave that happy ending. They want a film filled with fun and witty banter, the much-expected traumatic issue that takes our couple apart, and the eventual bringing back together of said couple.

The romantic comedy, while succeeding greatly in the 1990s, has been with us for a long time. Let’s take a look at the best the genre has put out there.

10. 10 Things I Hate About You (1999)

10 Things I Hate About You is a romantic comedy that stars Joseph Gordon-Levitt as a brand-new high school student, Cameron, who immediately falls for Bianca (Larisa Oleynik). With the help of his new friend, Michael (David Krumholtz), Cameron begins to plan how he will woo her. Making life difficult for Bianca, whose father refuses to allow her to date unless Bianca’s sister, Kat, dates. Kat, though, has no desire to date the Neanderthals at her school. Then she is approached by high school bad boy, Patrick Verona (Heath Ledger).

9. Crazy, Stupid, Love (2011)

Love comes in many shapes and sizes in Crazy, Stupid, Love, a romantic comedy that follows a number of different characters on an interconnected journey of true love. Steve Carell leads an ensemble cast as Cal Weaver, a man who seeks love after his wife calls it quits after years of marriage. Ryan Gosling shows up as Jacob Palmer, a young man who teaches Cal the art of seduction. Who winds up in who’s bed is all part of the fun.

notting hill hugh grant julia roberts

8. Notting Hill (1999)

Hugh Grant and Julia Roberts knock it out of the rom-com park in Notting Hill, a film directed by Roger Mitchell from a script by Richard Curtis. The romantic comedy follows William Thacker (Grant) a very average-looking bloke living a very average life who is the owner of a very average travel bookstore. William’s average life jumps a notch or two when super famous movie star Anna Scott pops in to find a book. William falls immediately, for Anna it takes a little more time as life’s complications of being a famous movie star appear to be more than they can handle.

7. When Harry Met Sally... (1989)

“I’ll have what she’s having.” It is one of the more classic scenes in movie history when Meg Ryan’s Sally shows Billy Crystal’s Harry, just how easy it is to fake an orgasm during dinner at a restaurant. The romantic comedy, written by Nora Ephron and directed by Rob Reiner, tries to answer the age-old question, can men and women ever just be friends? Harry and Sally are trying to figure it out, which leads to some memorable moments.

time travel movies

6. Groundhog Day (1993)

At first blush, you might be thinking the same thing we did – Groundhog Day? A romantic comedy? Seriously? Well, at second blush you may see the light. This Harold Ramis film stars Bill Murray as TV weatherman Phil Connors who is embarking on his annual trip to Punxsutawney to report on the Groundhog Day activities. His cynicism and half-heartedness turn his one day into many, living the same day over and over. But where is the romance, you ask?

Well, it comes in the form of Andie McDowell, who is Phil’s news producer and one he tries each Groundhog Day to seduce and bed. Over time, Phil learns how to become an actual decent human, but does he get the girl? So, is this a rom-com or just a com-com? Let’s see how we feel tomorrorw. “I’ve got you, babe.”

5. Four Weddings and a Funeral (1994)

British scribe Richard Curtis got his romantic comedy career started with his script for Four Weddings and a Funeral. The film stars Hugh Grant and Andie McDowell as star-crossed lovers who continue to chance meet at their friends’ social gatherings. Life continues to take them in separate directions. Will they get one final shot at happiness together?

4. Silver Linings Playbook (2012)

Mental health takes center stage in Silver Linings Playbook, a romantic comedy starring Bradley Cooper, Jennifer Lawrence, Robert De Niro, and Jacki Weaver. The film follows Pat Solitano Jr. (Cooper) who finds himself back at his parent’s (De Niro and Weaver) home after being released from a psychiatric hospital for bipolar disorder. Pat is determined to win back his estranged wife. To do so, Pat enlists the help of Tiffany (Lawrence), who promises to help if Pat promises to enter a dance competition with her.

3. Roman Holiday (1953)

We go into the “way back” machine to find this plucky romantic comedy starring screen legends Gregory Peck and Audrey Hepburn in a film that made everyone fall in love with her, not just Gregory Peck. Here, Peck plays an American journalist looking for a scoop to save his writing career. Hepburn is a princess who is tired of saying and doing the right thing. When they meet, one of them is going to get what they want.

2. The Princess Bride (1987)

This romantic comedy has it all. A princess and a pirate, Prince Humperdinck, a Sicilian, a giant, a Spanish fencing master seeking revenge, and a six-fingered man. Put it all together and you have The Princess Bride, one of the most enduring romantic comedies ever, disguised as an action-adventure piece. Cary Elwes, Robin Wright, Mandy Patinkin, Chris Sarandon, and Wallace Shawn star in this beloved classic fairy tale.

1. Annie Hall (1977)

Woodie Allen established himself as a comedic genius with Annie Hall, a film that won four Academy Awards including Best Picture, Best Actress, Best Original Screenplay, and Best Director. The Allen romantic comedy stars Allen as Alvy Singer, a man who looks back in reflection as to why his relationship with Annie Hall (Diane Keaton) failed, much like his previous marriages. In taking home the Best Picture award, it stopped Star Wars from winning that year.