Best Romantic Comedies of All Time

Romantic comedies or rom-com are one of the best genres in the movie industry. Not only are they comforting, but they are also heartwarming. They often generate real feelings and emotion that are worth watching. However, despite them being a hit at the box office once, their cultural provenance has definitely been lost. TechTrends put together a list of the best romantic comedies of all time; Keep reading to see what they are.

Although the genre has fallen into a slump during the last decade, they are slowly making their way up once again. With theater recovering from Covid-19, e new age for romantic comedies seems to be in the making. 2023 has been an incredible year for romantic comedies so far as movies such as A Tourist’s Guide to Love and Your Place or Mine have already come out and they are popular. With all of that in mind, here are the best romantic comedies of all time to watch when you feel down or need a good love story. Without further ado, let’s get into it.

Best Romantic Comedies of All Time

It is time to dive deep into some of the best rom-coms of all time, with these movies having some sort of simplicity and familiarity to them that is engaging and fun to watch. Notwithstanding the attempts to make good rom-coms during the past decade, it is now that they are rising up once again. Here are the best rom-coms ever.

12. The Proposal 2009

  • Genre: Romance/Comedy
  • Director: Anne Fletcher
  • Stars: Sandra Bullock, Ryan Reynolds, Betty White, Oscar Nunez, Malin Åkerman
  • Rating: Rotten Tomatoes 45%, IMDb 6.7

One of the best rom-coms of all time is The Proposal, in which Ryan Reynolds portrays Sandra Bullock’s assistant, who will turn into being her fiancé. While there’s nothing fresh in this movie, there is a refreshing amount of fuzzy and warm feeling. Teaming up Bullock and Reynolds and was dreamy, as they share amazing chemistry. The movie revolves around a female executive who wrangles her assistant into acting like he is her fiancé, so she won’t get deported to Canada. The two played off one another incredibly with their impeccable comedic timing. The Proposal is one of the best romantic comedies of all time.

11. Pretty Woman 1990

  • Genre: Romance/Comedy
  • Director: Garry Marshall
  • Stars: Julia Roberts, Richard Gere, Laura San Giacomo, Hector Elizondo, Jason Alexander
  • Rating: Rotten Tomatoes 64%, IMDb 7.1

Pretty Woman is one of the best romantic comedy movies of all time, where Julia Roberts portrays the role of Vivian Ward. Roberts’ performance of this character brought her a Golden Globe Award as well as a nomination for the Academy Award for Best Actress. Notwithstanding the movie being intended to be a dark story about sex work and class at first, it was re-conceived later. Roberts’ character is a sex worker who earns a lot of money when she runs to Richard Gere’s character Edward Lewis, who is a cold and lonely businessman. This is for sure one of her best performances, having every viewer rooting for her.

Read more: Best Julia Roberts Movies of All Time

10. Friends with Benefits 2011

  • Genre: Romance/Comedy
  • Director: Will Gluck
  • Stars: Mila Kunis, Justin Timberlake, Woody Harrelson, Emma Stone, Patricia Clarkson
  • Rating: Rotten Tomatoes 68%, IMDb 6.5

One of the most well-known and best romantic comedies of all time is the movie Friends with Benefits. In this romantic comedy, Mila Kunis acts alongside Justin Timberlake, and the movie’s title sums up the whole thing short and sweet. The two are strangers who quickly become friends. However, their physical relationship leads to some problems and complications. Notwithstanding the movie being cliché, it is undoubtedly a hilarious and entertaining one. In addition, the two stars have great on-screen chemistry. The movie got five nominations for awards, and the audience received the movie well. Friends with Benefits is among the top and the best rom-coms ever.

Read more: Best Mila Kunis Movies of All Time

9. 10 Things I hate about you 1999

  • Genre: Romance/Comedy
  • Director: Gil Junger
  • Stars: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, Larisa Oleynik, Gabrielle Union
  • Rating: Rotten Tomatoes 71%, IMDb 7.3

Joseph Gordon-Levitt plays the role of a sophomore student named Cameron and he falls for Bianca, portrayed by Larisa Oleynik. However, he realizes that Bianca is not allowed to date until her older sister Kat, played by Julia Stiles, is dating. Cameron looks for a solution and asks senior Joey Donner (Andrew Keegan), his new friend, to find a guy for her. They have Heath Ledger’s character Patrick Verona in mind. This is indeed one of the best romantic comedies of all time that you do not want to miss.

8. Crazy, Stupid, Love 2011

  • Genre: Romance/Comedy
  • Directors: Glenn Ficarra, John Requa
  • Stars: Ryan Gosling, Emma Stone, Lio Tipton, Steve Carell, Julianne Moore
  • Rating: Rotten Tomatoes 79%, IMDb 7.4

This amazing romantic comedy movie got elevated by Ryan Gosling’s effortless charm and his chemistry with amazing actress Emma Stone. The story revolves around a middle-aged man, portrayed by Steve Carell, who recently got separated. His new friend Jacob, played by Gosling, shows him how to pick up women at bars. Stone shines bright in Crazy Stupid Love as a young attorney who is stuck with the wrong guy and his crazy family. However, when her character decides to have a one-night stand with Gosling’s, things take a turn. The sexual chemistry between the two actors definitely helped them further in their careers. Therefore, this has also made it to our list of the best romantic comedies of all time. We strongly recommend it.

Read more: Best Steve Carell Movies of All Time

7. Clueless 1995

  • Genre: Comedy/Romance
  • Director: Amy Heckerling
  • Stars: Paul Rudd, Alicia Silverstone, Brittany Murphy, Stacey Dash, Donald Faison
  • Rating: Rotten Tomatoes 81%, IMDb 6.9

Clueless is another one of the best romantic comedies of all time, which tells the story of the life of a super-popular high school girl, Cher. When she helps out one of the new students, Tai, and gives her a makeover, Cher sees that she becomes more popular than her. Paul Rudd portrays the role of John Lucas, Cher’s former step-brother. In this movie, Rudd is charming and young, playing the grounding voice for Cher. Although this was one of his earliest roles, Rudd performs greatly and makes the movie fun. The incredible cast made this one of the funniest and most romantic movies ever.

Read more: Best Paul Rudd Movies of All Time

6. There’s Something About Mary 1998

  • Genre: Romance/Comedy
  • Directors: Peter Farrelly, Bobby Farrelly
  • Star: Cameron Diaz, Ben Stiller, Matt Dillon, Chris Elliott, Lin Shaye
  • Rating: Rotten Tomatoes 84%, IMDb 7.1

Cameron Diaz is a master of romantic comedies and she shone once again in There’s Something About Mary. She portrays the role of the titular Mary, and she has an important role in making the movie hilarious and unforgettable. Multiple men are trying to persuade her, and Diaz gives a powerful performance, making this one of the funniest films of the 90s. There really is something about Mary that makes all neurotic men desire. For her performance, Diaz won the New York Film Critics Award as Best Actress and shocked many as comedy did not appear to be something of an award material. This is one of the best romantic comedies of all time featuring Cameron Diaz. We highly recommend this hilarious film.

5. Notting Hill 1999

  • Genre: Romance/Comedy
  • Director: Roger Michell
  • Stars: Julia Roberts, Hugh Grant, Rhys Ifans, Hugh Bonneville, Gina McKee, Emma Chambers
  • Rating: Rotten Tomatoes 84%, IMDb 7.2

Notting Hill broke the all-time British Box office record in 1999. The story is about a London Bookseller played by Hugh Grant and an actress, portrayed by Julia Roberts. She portrays the character of Anna Scott, who is famous but fragile. The theme of the film revolves around love between people of various social classes and Roberts and Grant’s chemistry shows that quite beautifully. Notwithstanding being attractive and successful, Anna is insecure and concerned about losing her reputation, money and building relationship with men. Her portrayal of those concerns is excellent and this is one of the best romantic comedies of all time.

4. 500 Days of Summer 2009

  • Genre: Romance/Comedy
  • Director: Marc Webb
  • Stars: Joseph Gordon-Levitt, Zooey Deschanel, Chloe Grace Moretz
  • Rating: Rotten Tomatoes 85%, IMDb 7.7

500 Days of Summer is another one of the best romantic comedies of all time, which is worth watching. The movie features Joseph Gordon-Levitt playing the role of Tom, who is a greeting-card writer and a romantic man. When his girlfriend named Summer, played by Zooey Deschanel, breaks up with him, he is caught off-guard. He looks at their 500 days that they were together to find out what happened to their relationship and by doing so, he realizes what his true passion in life is. Don’t miss this wonderful movies.

3. Amelie 2001

  • Genre: Romance/Comedy
  • Director: Jean-Pierre Jeunet
  • Stars: Audrey Tautou, Mathieu Kassovitz, Lorella Cravotta
  • Rating: Rotten Tomatoes 89%, IMDb 8.3

The third one on the list of the best romantic comedies of all time is Amelie. Amelie Poulain, portrayed by Audrey Tautou, is a girl who has been away from the real world ever since she was a young girl as her parents were eccentric. They thought that Amelie has a heart defect. With all the isolation, Amelie’s only company was her active imagination. When she turned 18, she went to Paris and became a waiter at a very eccentric café, experiencing for the first time what life has to offer. She finds out that helping people makes her happy and it is then when she falls for Nino, played by Mathieu Kassovitz.

2. Annie Hall 1977

  • Genre: Romantic/Comedy
  • Director: Woody Allen
  • Stars: Woody Allen, Diane Keaton, Shelley Duvall, Paul Simon
  • Rating: Rotten Tomatoes 97%, IMDb 8

Another one of the best romantic comedies of all time is Annie Hall, directed and starred by Woody Allen. When Woody Allen released the movie Annie Hall, he went into a more mature filmmaking as he first established himself as a joke-maker. The movie is about a New York comedian, played by Allen, as well as an eccentric lounge singer, portrayed by Dian Keaton, broke the romantic comedies’ mold, as it brought a darker edge to the genre. Moreover, Keaton’s Oscar-winning performance made this movie a success. Allen won prizes for directing and writing this movie. In addition, the film became one of the few comedies to win Best Picture.

Read more: Best Woody Allen Movies of All Time

1. The Big Sick 2017

  • Genre: Romance/Comedy
  • Director: Michael Showalter
  • Stars: Kumail Nanjiani, Emily V. Gordon, Zoe Kazan, Holly Hunter, Ray Romano
  • Rating: Rotten Tomatoes 98%, IMDb 7.5

The first one on the list of the best romantic comedies of all time is The Big Sick, starring Kumail Nanjiani. He plays the role of a fictionalized version of himself. He is an immigrant from Pakistan who is keen on becoming a stand-up comedian in NYC. Following one of his shows, he meets with a girl named Emily, portrayed by Zoe Kazan. The two begin to feel something for one another, while Kumail’s parents are eager to have him meet with a Pakistani girl, insinuating an arranged marriage. This causes an argument between him and Emily, leading to a break up. Don’t miss this wonderful movie.

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