1950s To Now: The Best Rom Com From Every Decade

There’s no time like Valentine’s Day to celebrate romantic comedies.

As many of us go on rom-com bingeing sprees, we’re looking for a touch of inspiration and organization to drive us through which classic romantic comedies to watch. The genre has existed longer than film, going all the way back to Shakespearean romantic comedies like Much Ado About Nothing and The Taming of the Shrew, which have both inspired some of our favorite modern flicks.

Because romantic comedies are a staple of film, it’s fitting to go back to their roots for the holiday of love and find the best rom-com for every decade. Although there were some incredible romantic comedies even earlier, we’re starting in the 1950s as we kick off a marathon through love and time.

Some Like It Hot (1959)

Some Like It Hot isn’t just a rom-com — it’s a buddy film, a crime comedy, a musical. Starring Marilyn Monroe as a comedic romantic lead alongside Jack Lemmon and Tony Curtis, it’s considered one of the best films of all time for good reason. Using a Shakespearean trope, the two male leads disguise themselves as women to evade the local Mafia, during which they befriend and try to woo Marilyn’s Sugar Kane. Through ridiculous antics, the three leads meet other characters who they vary between seducing, tricking, and falling in love with in this classic romantic comedy of errors.

Honorable Mentions: Singin’ in the Rain (1952), Roman Holiday (1953)

Breakfast at Tiffany’s (1961)

Before there was Molly Ringwald, Meg Ryan, Julia Roberts, and Emma Stone, there was Audrey Hepburn. She is often considered the first queen of romantic comedy, starring in several of the genre’s best early films. But the most iconic was probably her 1961 turn in Breakfast at Tiffany’s, based on Truman Capote’s 1958 novella of the same name. Audrey plays Holly Golightly, a country girl turned Manhattan socialite who gets mixed up in a drug ring to support her brother Fred. With many miscommunications and mishaps, as well as a moving story of strangers to lovers, Breakfast at Tiffany’s is easily the best rom-com of the 1960s.

Honorable Mentions: Funny Girl (1968), The Graduate (1967)

What’s Up, Doc? (1972)

If Audrey Hepburn was the rom-com queen of ‘60s, Barbra Streisand took the title for the 1970s. Starring in What’s Up, Doc? in addition to A Star Is Born and The Way We Were, Barbra was the romantic “it girl.” What’s Up, Doc? follows Barbra’s Judy Maxwell who notoriously stirs up trouble with her rebellious, yet intelligent, disposition. She wins over musicologist Dr. Howard Bannister in what ensues as a classic bag swap mishap of a film. With slapstick humor that pays homage to the early films of the ‘20s, ‘30s, and ‘40s along with more modern acting styles and more progressive romance, What’s Up, Doc? is a must-see ‘70s film to add to the catalogue.

Honorable Mentions: Grease (1978), Annie Hall (1977)

When Harry Met Sally (1989)

Often lauded as the best rom-com of all time, When Harry Met Sally easily takes the cake for the best rom-com of an era known for its romantic comedies. Starring Billy Crystal and Meg Ryan and created by Nora Ephron, the film answers the age-old question of if men and women can just be friends. Because it’s a rom-com, you can probably guess the answer. Even still, with a 2025 Super Bowl commercial nodding to the “I’ll have what she’s having” scene, When Harry Met Sally is one of the rare films to truly stand the test of time because of its memorable performances, sharp script, and perennial philosophical musings.

Honorable Mentions: Sixteen Candles (1984), The Princess Bride (1987)

The Wedding Singer (1998)

Sure, Julia Roberts had some major hits in the ‘90s, and Nora Ephron’s films continued to skyrocket. But Adam Sandler found his place on the rom-com map in The Wedding Singer by bringing the charming lead of the male “schlub” to fruition. Every guy has had his heart broken at least once and been tempted to fall apart, but amidst falling apart (and writing some sick tunes), Adam’s Robbie finds hope in Drew Barrymore’s Julia. It proves that love really does make everything better, and beyond that, that music, friendship, and a good sense of humor are necessary parts of finding “the one.” 

Honorable Mentions: 10 Things I Hate About You (1999), You’ve Got Mail (1998), Pretty Woman (1990)

Love Actually (2003)

What other film do people watch on repeat year after year? Love Actually is the film for Christmas, Valentine’s Day, and any other time you need a pick-me-up. It perfected the art of weaving seemingly disconnected stories and characters into one another to create a satisfying finale that not only shows how “love really is all around us,” but how it brings people together from all walks of life. With a star-studded cast of all ages, Love Actually achieved what several films after have tried to do and failed (i.e. Valentine’s Day, New Year’s Eve) by becoming a timeless depiction of various interwoven tales of love.

Honorable Mentions: How to Lose a Guy in 10 Days (2003), Just Like Heaven (2005), Forgetting Sarah Marshall (2008)

Crazy, Stupid, Love (2011)

The 2010s saw a big decline in romantic comedies as society started to move past the heteronormativity of gendered stereotypes often portrayed in rom-coms. Women grew tired of the trope that we needed to be “saved,” so rom-coms had to adapt. Luckily, earlier in the decade, Crazy, Stupid, Love stands out as a shining gem of feminist love stories. With two men (Steve Carrell and Ryan Gosling) as the protagonists, the film is less about finding someone to settle down with and more about how complicated and challenging love can be … but that it’s always still worth it in the end.

Honorable Mentions: Trainwreck (2015), Silver Linings Playbook (2012)

Bros (2022)

As we get into the current decade, rom-coms needed a bit of a makeover. Bros achieves just that with its romantic leads, Billy Eichner and Luke Macfarlane. A twist on the classic rom-com, Bros works to point out and make fun of the stereotypes that preceded it while progressing with a queer love story. As Bobby and Aaron fall for one another, there are classic mishaps and miscommunications necessary to any rom-com, but in this case, they are also engrained in queer culture. Bros is funny, unique, and will still make you cry in the end, making it the perfect rom-com to encapsulate the modern era.

Honorable Mentions: Palm Springs (2020), Licorice Pizza (2021)