It’s the month of love, and to honor the life and teachings of St. Valentine, I wanted to share my top romantic comedies recommendations for your viewing pleasure. I tried to have a healthy balance of genre staples and lesser-known gems for you to discover. In concocting this list, I held myself to some hard and fast rules, which are as follows:

Rule #1: These are Romantic, hyphen, Comedies. The film can flirt with other genres, but it must primarily be a comedy (apologies to Love Story and the many Stars Are Born).

Rule #2: The movie must adhere to most of the broadly-accepted tropes of the genre that were molded through the 40s and truly synthesized in the 90s.

Rule #3: The film must be enjoyed by yours truly (more apologies to Notting Hill fans, or ‘Hill Heads’). If your favorite romantic comedy didn’t make the cut, you should still watch it this weekend!

10) Palm Springs (2020): This Sundance darling was a bright spot during the pandemic. Its clever script makes great use of a high-concept premise, and features standout performances by Cristin Milioti and Andy Samberg. Try going into this one knowing as little as possible of the plot. Palm Springs is rated R, runs 90 minutes, and is available to stream on Hulu.

9) Annie Hall (1977): This Best Picture winner requires separating the art from the artist, but is a classic that revitalized the genre. Diane Keaton is electric and deservedly took home the Oscar for her performance. Annie Hall is rated PG, runs 93 minutes, and is available to stream or rent on Starz or Amazon Prime.

8) My Best Friend’s Wedding (1997): Is Julia Roberts as Julianne Potter the most sympathetic on-screen villain? In a clever departure from the formula, we’re asked to root for the girl who arguably shouldn’t get the guy—and despite how petty and desperate Roberts gets, we never stop relating to her. My Best Friend’s Wedding is rated PG-13, runs 105 minutes, and is available to stream on Netflix.

7) Moonstruck (1987): An Oscar-winning performance by Cher and a truly bizarre and ever-watchable Nicolas Cage steer this smart, iconic romance. You’ll spend the entire movie smirking to yourself or laughing out loud. Moonstruck is rated PG, runs 102 minutes, and is available to rent on Amazon Prime and Google Play.

6) You’ve Got Mail (1998): Outside of bringing dating into the digital era, this culture-clash romance doesn’t try anything new, but who cares? With Tom Hanks and Meg Ryan at the height of their stardom, and a charming and sentimental script by Nora Ephron, you’re in safe hands. You’ve Got Mail is delightful, predictable, and immensely rewatchable. You’ve Got Mail is rated PG, runs 120 minutes, and is available to stream on Hulu and HBO Max.

5) Bringing Up Baby (1938): Howard Hawks’s hilarious slapstick was a flop on release, but has since been rightfully reclaimed as a pioneer of the screwball comedy. The film stars two titans of the genre: Cary Grant at his most charmingly exhausted, and Katherine Hepburn on the cusp of entering a historic rom-com run. Bringing Up Baby is rated G, runs 102 minutes, and is available to stream or rent on The Criterion Channel or Amazon Prime.

4) The Big Sick (2017): A staple of the recent rom-com resurgence, this loosely-autobiographical story from co-writer and star Kumail Ninjiani is sweet and funny, and an authentic look at the challenges of modern dating. The Big Sick is rated R, runs 119 minutes, and is available to stream on Amazon Prime.

3) Some Like It Hot (1959): The iconic Billy Wilder directs this brazen, hilarious smash hit that was instrumental in ending the archaic Hollywood censorship code. The dynamite assembling of Tony Curtis, Jack Lemmon, and Marilyn Monroe contribute to arguably one of the best films of all time, full stop. Some Like It Hot is rated G, runs 122 minutes, and is available to rent on Amazon Prime and Google Play.

2) Sleepless in Seattle (1993): It’s a heat check to not have your romantic leads interact for 95% of the movie and still keep the audience completely invested in their relationship. It’s arguably the best pairing of director Nora Ephron and stars Tom Hanks and Meg Ryan. The film is funny and heartwarming, with a real sense of pathos, and a truly satisfying final 10 minutes. Sleepless in Seattle is rated PG, runs 105 minutes, and is available to rent or stream on Starz and Amazon Prime.

1) When Harry Met Sally… (1989): Can you make a better movie than this? Perched in the middle of director Rob Reiner’s unreal eight-year run of movies, he delivers on the premise, “Can a man and a woman ever just be friends?” What follows is the unbelievable chemistry between stars Billy Crystal and Meg Ryan, and a crackling, hilarious script from Nora Ephron. When Harry Met Sally… reminds you why we love movies in the first place. It should be a yearly required viewing. Go watch it right now. When Harry Met Sally… is rated R, runs 96 minutes, and is available to stream or rent on Showtimes and Amazon Prime.


Did I overlook your favorite rom-com? Did I include one you absolutely abhor? Is love meaningless and are our pathetic attempts to find companionship a disturbing reminder of the vacant emptiness of life? Leave a comment below and let me know!