Romantic comedies (or “rom-coms” for short) are a staple of Hollywood cinema. Pairing together two established stars with a decent script, and usually, one unique variable to set it apart from all other similar films is a sure-fire way for studios to cash in. Because of their low budgets, typically simple storylines, and profitable nature, many viewers and critics alike tend to write off rom-coms as just “fluff,” and unimportant in the scheme of cinema as a whole. Although many rom-coms are just that, there does exist a number that has successfully crafted compelling stories with great performances and a unique take on the genre to build upon one of the largest categories in American film history. 

With Valentine’s Day steadily approaching, I have crafted a list of 14 romantic comedies (for the 14 days leading up to Valentine’s Day) which I believe represent the genre very nicely and give a well-rounded history of it. Some of these films are Oscar-winners and some have less than 50% on Rotten Tomatoes, but that is part of the beauty of rom-coms…simply put, they don’t need to be perfect and their imperfections are often what makes them so enjoyable.

14. “About a Boy” (2002)

Hugh Grant is to Britain what Tom Hanks is to America. Relatable, charming, and talented, both actors excel at the rom-com because of how likable they are and how easily audiences can relate to and empathize with them. Hugh Grant, in particular, has been in several romantic comedies over the years, including classics like: “Love Actually,” “Four Weddings and a Funeral,” and “Notting Hill.” With many memorable rom-com roles, Grant has cemented himself as a leading man in the genre. However, out of all the rom-com he’s been in, I believe his best performance is in the 2002 romantic comedy “About a Boy.” “About a Boy” tells the story of Will Freeman, a wealthy yet irresponsible and immature man who pretends to have a son so that he can date women in a single parent’s support group. After one of the women’s sons, Marcus, discovers Will’s plan, he blackmails Will into becoming his friend. As Will learns life lessons from Marcus, he also begins to fall in love with a woman who believes his lie that he has a son. It is a rom-com that is truly funny and features some fantastic British humor, all the while it successfully adds a positive message (as many rom-coms try to do) of having to be able to care about not only others but also yourself before you can let someone else into your life. It stars Grant along with Rachel Weisz, Toni Collette, and a young Nicholas Hoult. It is equal parts charming and endearing and a good first venture into the rom-com genre. 

13. “13 Going On 30” (2004)

What is so wonderful about rom-coms is their generic hybridity. Rom-coms don’t have to be just romantic comedies, they can have elements of other genres like sci-fi, drama, historical fiction, horror, musical and in the case of “13 Going on 30,” fantasy. This film tells the story of an insecure girl named Jenna who on her 13th birthday in 1987 wishes that she was older. Her wish comes true and she literally wakes up in the year 2004 in the body of her future self at the age of 30. Thrust into the modern world as her new self, Jenna soon realizes that the person she grows up into may not have been everything she had always dreamed she’d be. Similar to the 1980s classic, “Big,” this movie has all the essential romantic comedy tropes, but its fantasy element really separates it from other similar films. Jennifer Gardner plays grown-up Jenna effortlessly, as we still feel as though she’s the 13-year-old Jenna from the beginning of the movie. And adding to the film’s charm is the movie that widely introduced audiences to Mark Ruffalo, who plays Jenna’s childhood best friend and eventual romantic interest, Matt. From an office-party “Thriller” dance flash mob to a sleepover where the characters belt out “Love is a Battlefield” this movie is truly just a ton of fun. “13 Going on 30” is not a perfect film by any means but it’s funny, sweet, and has a great romantic plotline, making it an essential rom-com to be viewed. 

“13 Going On 30” | IMDB

12. “Never Been Kissed” (1999)

One of the most popular kinds of romantic comedies is the teen rom-com. Often taking place in a high school setting, some of the most memorable include the likes of “10 Things I Hate About You,” “Clueless,” “Pretty in Pink,” etc. However, one that is highly representative of them all and is genuinely such a fun film is “Never Been Kissed.” Released in 1999, “Never Been Kissed” follows Josie Geller, a young reporter for the Chicago Sun-Times who, on her first research assignment, goes undercover in a high school and registers as a student. With terrible memories of her time in school, Josie tries to navigate her way through high school once again, only this time around trying to infiltrate the popular clique. Problems soon arise for Josie as she deals with the pressures of her journalist assignment and pretending to be a student, while she starts to fall for her English teacher. “Never Been Kissed” can be cheesy at times but a funny script and a relatable and vulnerable performance from Drew Barrymore help to make it something special. The film never gets too serious which works well here as it is a great example of a rom-com that doesn’t try to be anything more than what it is, fun and heartwarming entertainment. “Never Been Kissed” is the type of movie that you can watch whenever and know you’ll enjoy it, it is a feel-good movie and one that is sure to put you in a good mood.  

11. “Lost in Translation” (2003)

What separates “Lost in Translation” from the rest of the movies on this list is that it is the only movie on here that could arguably not be classified as a rom-com. Why would this film be on a list strictly for rom-coms you may ask? Well, the answer is because this movie can definitely be classified as a romance, and it can also definitely be classified as a comedy. Although it doesn’t have the same sensibilities and tones as most rom-coms, this movie still has the two main elements that define the genre, which is why it is still deserving of a spot on my list. “Lost in Translation” follows Bob Harris, an aging actor from America who is in Tokyo to film a Japanese whiskey commercial. Staying at the same hotel Bob is staying at is recent college graduate Charlotte, who is in Japan with her photographer husband for his work. In a new city and by themselves, Bob and Charlotte’s paths cross in the hotel and friendship between the two soon forms… whether or not it blossoms into something more than a friendship is something they have to decide. Starring Bill Murray and Scarlett Johansson in the lead roles, “Lost in Translation” is easily one of my favorite movies of all-time. It is artfully and delicately directed, and the performances are so subtle and nuanced that the chemistry between the two main characters seems so authentic. Bob and Charlotte are nothing alike on paper, but they still seem to have a genuine connection that transcends all of their differences and makes the movie all the more captivating. “Lost in Translation” is Sofia Coppola’s second feature-length film and also her best, earning her an Oscar for Best Original Screenplay. This movie also gave Bill Murray his only Oscar nomination to date, for his role as Bob Harris. “Lost in Translation” is funny, heartbreaking, beautiful, and devastating all at once, and is probably the most dramatic of the movies on this list; but its bittersweet feel and comedic nature make it deserving of a spot nonetheless and also help it to be categorized as a romantic comedy, although extremely unique in comparison to the rest of the genre. 

10. “500 Days of Summer” (2009)

 “500 Days of Summer” does not have an inventive story by any means, as it follows a couple before, during, and then after their relationship has ended. However, where “500 Days of Summer” sets itself apart from other rom-coms with this generic storyline, is the way in which the plot actually unfolds. After Tom is dumped by his girlfriend Summer, he thinks back upon the 500 days he has known her and tries to pick apart where things went awry. Jumping back and forth between a multitude of days in their almost 2 years of knowing one another, the movie tracks the trajectory of Tom and Summer’s relationship throughout its highs and lows. With a simple concept, “500 Days of Summer” is made exponentially better by the artistic and creative way the story is told. Joseph Gordon-Levitt and Zoey Deschanel play Tom and Summer respectively, and watching them during their “honeymoon” phase and also during the obvious deterioration of their relationship is really quite heartbreaking. “500 Days of Summer” can be rather serious at times but its somewhat avant-garde and artistic nature help to provide a lot of comedic relief, and makes an otherwise fairly depressing breakup film a more lighthearted movie about love, romance and the problems that can arise from dating. With an exceptional and entertaining plot, fantastic acting, and a particularly innovative and unconventional storytelling style, “500 Days of Summer” is definitely a rom-com worthy of watching and one that is sure to put a smile on your face during its first viewing, and all the viewings afterward.  

9. “Pretty Woman” (1990)

A major factor in determining whether or not a rom-com will be successful is the chemistry between the two lead actors. No matter how good the script is, a romantic comedy will fall flat on its face if the audience doesn’t buy into the romance of the on-screen couple. A great example of a good movie made better by the chemistry of the two leads is the 90’s classic “Pretty Woman” starring Richard Gere and Julia Roberts. This movie tells the story of a very wealthy businessman named Edward who pays a prostitute, Vivian, to pretend to be his girlfriend. Although their relationship begins based merely on a monetary proposal, the two soon begin to develop real feelings for one another and try to make their two completely different lifestyles work. “Pretty Woman” is one of the most financially successful rom-coms of all time and it is also what catapulted Julia Roberts into stardom. Roberts and Gere have amazing chemistry in this film, and as you’re watching you feel as though the couple on screen is not only falling in love but that they’re also genuinely having fun in the process. The two play flawlessly off of one another which helps to cement “Pretty Woman” as a staple rom-com. 

“Pretty Woman” | HollywoodReporter.com

8. “Sleepless in Seattle” (1993)

Most rom-coms try to give the two romantic leads as much screen time together as possible, which is a formula that obviously worked for the previous movie on my list, “Pretty Woman.” However, in the case of “Sleepless in Seattle,” the two leads share less than 5 minutes together on the screen, but the movie still manages to make it work. “Sleepless in Seattle” tells the story of Sam, a recently widowed man with an 8-year-old son whom he lives in Seattle with. After calling into a radio talk-show to discuss his grief after the death of his wife, women all over the country fall for Sam, including Annie, a reporter from Baltimore. Inspired by the film, “An Affair to Remember” Annie writes a letter to Sam asking to meet on the observation deck of the Empire State Building on the night of Valentine’s Day, which her friend mails for her. Although Annie is already in a relationship, and Sam begins one as well, Sam’s young son decides to take matters into his own hands to make their romantic meeting happen, after he reads Annie’s letter addressed to his dad. Tom Hanks and Meg Ryan star in this film and it is one of the three romantic comedies they did together. With an already established chemistry between the two, these two actors didn’t even need to spend time together on screen for audiences to understand and feel the tangible chemistry between the two. “Sleepless in Seattle” is a heartwarming flick that delivers on all spectrums for a romantic comedy and is one centered around Valentine’s Day making it all the more relevant for viewing. 

“Sleepless in Seattle” | IMDB

7. “Forgetting Sarah Marshall” (2008)

Judd Apatow is quite simply a comedic genius. He is responsible for bringing the adult comedy back to life and is the brain behind some of the best comedies made in the 21st Century and arguably all-time. With a number of instant-classics under his belt, the one that I believe most typifies the rom-com genre and is an exemplary model of just how funny romantic comedies can be is “Forgetting Sarah Marshall.” This film features an all-star cast including Jason Segel, Mila Kunis, Kristen Bell, Russell Brand, Paul Rudd, Bill Hader, and Jonah Hill. This movie is laugh-out-loud funny and only seems to get better with every re-watch. “Forgetting Sarah Marshall” tells the story of Peter Bretter (Segel) an aspiring musician who is dating one of television’s most popular stars, Sarah Marshall (Bell). After she abruptly ends their relationship and starts another with worldwide pop phenomenon Aldous Snow (Brand), Peter becomes extremely depressed. In an attempt to cheer himself up, Peter goes on vacation to Hawaii only to realize when he gets there, that his ex and her new boyfriend are staying in the same hotel as him. Comedy is not easy, but each and every actor in this movie is hilarious. Russel Brand steals every scene he’s in, and Mila Kunis (who is no rookie to the rom-com) gives her most memorable romantic comedy performance in this one, just edging out her role in “Friends with Benefits.” This movie is an essential Apatow feature, and also a fantastic entry into the genre. 

6. “Moonstruck” (1987)

A vital plotline that occurs in many romantic comedies revolves around the idea of family. Some rom-coms like, “My Big Fat Greek Wedding,” and “Hannah and Her Sisters,” make family the focus of the film, and one example that does it so well is the 1988 critically acclaimed picture, “Moonstruck.” Directed by the brilliant Norman Jewison and starring Cher (in an Oscar-winning performance) alongside a young Nicolas Cage, this movie is a quintessential entry into the romantic comedy genre. “Moonstruck” follows Loretta Castorini, a woman in her late thirties who has already been widowed. Loretta lives in New York with her very traditional Italian family who is extremely invested in her love life. After Loretta is proposed to by her boyfriend, Johnny, she insists that he invite his estranged brother to the wedding. While Johnny is away before their wedding, Loretta meets and falls quickly in love with his brother, Ronny. Not sure what to do, she turns to her some of her family members for help, who also seem to be having romantic issues of their own. With a fairly grounded premise, “Moonstruck” is in no way groundbreaking as far as romantic comedies go. However, “Moonstruck” is an example of a film where the sum of its parts adds up to something great. The characters seem real, the jokes are funny, and Cher steals the show with her relatable and hopeful performance as Loretta. There is something innately warm about this movie and it provides everything you could want from a rom-com. 

5. “The Princess Bride” (1987)

“The Princess Bride” is not only one of my favorite films, but is also a romantic-comedy that has so many different elements to it which help to make it so memorable. To quote the grandpa from the movie, it has, “Fencing, fighting, torture, revenge, giants, monsters, chases, escapes, true love, miracles…” It truly has everything. Directed in 1987 by Rob Reiner, “The Princess Bride” was not very popular upon its initial release, but through word of mouth and the proliferation of VHS tapes following its release, the movie has since gained a cult following over the years and has become a pop culture phenomenon. A story within a story, “The Princess Bride” starts with a young boy in bed with a fever who receives a visit from his grandpa. Reluctantly, the grandson allows his grandpa to read him an old adventure novel entitled, “The Princess Bride.” The narration from the grandpa as he reads the book is what comprises most of the film, as we follow the story in the novel of two lovers who will do anything to be together. This movie is campy, action-packed, hilarious and full of so many memorable lines and performances, but above all this movie is about love. Mixing present-day humor with a medieval love story works amazingly here, making “The Princess Bride” not only wildly unique but also a fantastic romantic comedy as well. 

“The Princess Vibe” | Studio Binder

4. “Some Like It Hot” (1959)

The oldest movie on my list comes in the form of the 1959 classic, “Some Like It Hot.” Very few movies actually withstand the test of time, and the few oldies that are revered are frequently thought of as “outdated.” However, in the case of “Some Like It Hot,” this could not be less accurate. Even after 60 years, all of the movie’s jokes still land, the story is still so much fun, and the performances are all still great. “Some Like It Hot,” tells the story of two band musicians, Joe and Jerry, who accidentally witness a mafia murder. With the mob now chasing them, Joe and Jerry disguise themselves as women and join an all-female jazz band to lay low. However, things get complicated when Joe falls in love with one of the girls in the band, and a rich man begins to fall in love with Jerry, who’s disguised as a woman. If this plot sounds familiar to you, it may be because this is the movie that directly inspired the Wayans’ brothers’ adaptation of it, with the 2004 cult classic, “White Chicks.” “Some Like It Hot” stars Tony Curtis and Jack Lemmon at the peak of their careers, and they have a flawless dynamic together in this film. This movie also stars Marilyn Monroe as Sugar, Joe’s love interest, and although today Monroe is often viewed simply as a pop culture icon of the 50s, this movie reminds you of just how talented she was as an actress. Don’t let the release year deter you from this classic, as “Some Like It Hot” is still hysterically funny today, and is definitely one of the greatest comedies of all-time and subsequently one of the best rom-coms too. Simply put, “Some Like It Hot” truly gives meaning to the word timeless. 

3. “When Harry Met Sally” (1989)

If you haven’t heard of this movie I can assure you that you know one of the most famous lines in all of cinema that comes from it, “I’ll have what she’s having.” “When Harry Met Sally” is the second film on my list to feature Rob Reiner, and it is also the second to feature Meg Ryan as well as Billy Crystal. Together, all three helped craft one of the most memorable romantic comedies ever created. The premise is very straightforward and does not have a major twist or anything of that nature, which is a testament to how brilliant the script and the performances of Ryan and Crystal were. “When Harry Met Sally” follows the two title characters, who first meet whilst arguing about whether or not men and women can stay in a platonic friendship. A decade after their first meeting, Harry and Sally meet again by chance and become good friends, attempting to stay just friends, without any romantic implications. “When Harry Met Sally” follows a simple premise and typifies a highly formulaic romantic comedy, but what makes it so memorable is that it truly is the best of its type. The writing, acting, and direction help to separate it from other similar films and propel it to its status as one of the greatest rom-coms and a staple of 80s cinema. 

“When Harry Met Sally” | USA Today

2. “Tootsie” (1982)

“Tootsie” takes from the spirit of “Some Like It Hot,” with the idea of a man falling in love with a female co-worker while pretending to be a woman; however, “Tootsie” adds to it critically. Whereas “Some Like It Hot” uses the idea of creating a false identity for comedic effect, “Tootsie” uses it to propel the story forward and also to develop the protagonist as he begins to understand women from the perspective of “being” one. “Tootsie” follows Michael Dorsey who can no longer find work as an actor. Desperate for work, Michael comes up with the idea of no longer trying to find jobs as an actor but instead as an actress. Michael then creates a character of his own named Dorothy Michaels, and he auditions as her at a soap opera where Dorothy gets a starring role. As Dorothy becomes more and more popular amongst fans of the show, Michael tries his best to juggle pretending to be a female actress while falling in love with his female co-star, Julie. Starring Dustin Hoffman and Jessica Lange, “Tootsie” features two amazing actors, both of whom being Oscar-winners. Their performances are human and you empathize with both throughout the film, truly caring about the story as it unfolds. This movie uses it comedic elements to its advantage by making an absurd premise feel grounded in reality while still addressing some serious concepts relevant to love, romance, work, gender, and sex throughout its runtime. Featuring some amazing supporting roles courtesy of Bill Murray and Teri Garr, this movie is a gem and one of the best rom-coms ever made.

1. “Annie Hall” (1977)

As I have mentioned throughout this list, rom-coms are often thought of as fluff and are very rarely recognized by both critics and audiences alike. However, one romantic comedy that was loved by fans, critically acclaimed by critics, a massive success at the box office, and swept award shows was 1977’s “Annie Hall.” Written, directed, and starring Woody Allen, “Annie Hall” is one of the only romantic comedies to be acknowledged by the Oscars winning in four of the five major categories for Best Picture, Best Screenplay, Best Director, and Best Actress. “Annie Hall” is one of the most unique movies I’ve ever seen: characters speak directly to the audience breaking the fourth wall, cartoons appear on the screen, and it has a meta/self-reflexive style of its own. The film is narrated by the protagonist Alvy Singer, who speaks to the audience as he tries to understand how his relationship with his ex-girlfriend Annie Hall went wrong. There are no faults with this movie, the direction is cutting edge, the script is smart and funny, and the performances are all top-tier, specifically Diane Keaton as the titular character, Annie Hall. Keaton and Allen made several movies together and even dated in real life so it is no surprise that their on-screen chemistry is some of the best in film history. While watching this movie so many of the jokes and tropes that are found in the majority of rom-coms are visible in it, and that is because “Annie Hall” set the standard for all other rom-coms after it. I rarely use the word “perfect” to describe films, but “Annie Hall” is one of the few that merits that kind of praise. Not only is it a perfect movie, but it truly is a perfect romantic comedy, and well deserving of the #1 spot on my list. 

“Annie Hall” | Variety.com

Full List:

14. About a Boy 

13. 13 Going on 30 

12. Never Been Kissed 

11. Lost in Translation 

10. 500 Days of Summer 

9. Pretty Woman 

8. Sleepless in Seattle 

7. Forgetting Sarah Marshall 

6. Moonstruck 

5. The Princess Bride 

4. Some Like It Hot 

3. When Harry Met Sally 

2. Tootsie 

1. Annie Hall 

Cover Photo: Elite Daily