The Best Netflix Original Romantic Comedy Movies Of All Time

Pictuers via Netflix

It’s hard to say definitively, but Netflix might have saved Rom-Coms from total extinction.

I grew up in the 80s & 90s when romantic comedies from major studios broke out in a big way. Directors like Nora Ephron, pairings like Tom Hanks & Meg Ryan, and megastars like Julia Roberts lit up the screens and the box office to make some of the best films of the genre.

Then, the 2000s started out strong as well. Ephron gave way to Nancy Meyers, Richard Curtis, & (mostly for the guys) Judd Apatow; Hugh Grant, Reese Witherspoon, & to a confusingly lesser extent, Adam Sandler took over the top spots; and business was still booming.

But, towards the latter part of the 00s and over much of the following decade, romantic comedies started to die off. Hollywood was much more focused on the burgeoning comic book/superhero action films that grossed billions and didn’t put as much effort into the smaller, star-driven rom-coms that served them so well for so long. Heck, I’m still not even sure that 2011’s No Strings Attached & Friends with Benefits aren’t the same movie.

Enter Netflix Original Movies.

Starting around 2018, the motivated streamer flooded the market with a series of successful rom-coms, mostly in the YA model, that made complete unknowns like Noah Centineo, Joey King, Lana Condor, & Jacob Elordi into young breakout stars. Even the co-star of one of the biggest surprise hits of 2023, the steamy yet silly rom-com Anyone But You, got the Netflix rom-com party started in those early years. While Netflix has struggled to get back to their golden age with some of their star-studded critical failures of the last couple years, they still produce more than any other studio and seem committed to keeping the genre alive.

So, without further ado, here are my top 5 Netflix Original Rom-Coms:

Always Be My Maybe

Director: Nahnatchka Khan
Cast: Ali Wong, Randall Park, Michelle Buteau, Daniel Dae Kim, James Saito, & Keanu Reeves
Rated: PG-13

Picture: Netflix

Directed by Fresh Off The Boat showrunner Nahnatchka Khan (Totally Killer), Always Be My Maybe is the perfect example of how the little things surrounding the leading couple can make your movie go from average to a stand out example in the genre.

Set in San Francisco, the story centers around Sasha Tran (played by “Beef” star Ali Wong) and Marcus Kim (played by MCU & “Fresh Off The Boat” star Randall Park), two childhood friends and next door neighbors who became close when the Kim family would have young Sasha over their home when her parents would leave her home alone to tend to their store. The two would remain friends until their teenage years when a sexual encounter during a grieving moment for them both after his mother’s sudden passing. After an argument that splits them apart, they fall out of touch for a very long time.

Fifteen years later, the two reunite in a chance encounter as Sasha, a celebrity chef, is back in the bay area overseeing the opening of her new restaurant. Hired to install air conditioning in Sasha’s temporary home, Marcus reconnects with Sasha and helps reacquaint her with the community she left behind. Fighting against career ambitions & past/current relationships, Marcus and Sasha must decide what is most important in their lives and see if what they had years ago was still worth saving.

While the chemistry between Wong’s Sasha & Park’s Marcus is undeniable in both the “rom” and “com” of the equation, what makes Always Be My Maybe unique is the details & care that went into making this film pop.

Starting with the largely Asian cast headlined by Wong & Park and supported incredibly well by Marcus’ father played by the original TMNT villain Shredder James Saito, Marcus’ hippy girlfriend Jenny played by “Sullivan & Sons” Vivian Bang, Sasha’s fiance played by “Lost” star Daniel Dae Kim, & cameo of the year candidate Keanu Reeves (part Chinese on his mother’s side) playing himself as Sasha’s post-fiance rebound. The cast is bolstered by Netflix rom-com all-star & comedian Michelle Buteau, who went on to star in her own show “Survival of the Thickest” in 2023.

Adding to the charm & deep Asian roots in the film is Marcus’ band Hello Peril, a name inspired by the term “Yellow Peril” – the “alleged threat to Western nations by East Asians”. With Park on vocals & co-writing the brilliantly funny songs with legendary producer Dan The Automator (Gorillaz, Handsome Boy Modeling School), Hello Peril’s amazing lineup features rapper Lyrics Born as Quasar, later seasons “House” co-star Charlyne Yi as Ginger, and Deadpool co-star Karan Soni as Tony. Songs like “Tennis Ball” which reference a blunder by Quasar in the movie and “I Punched Keanu Reeves” which plays at the film’s climax add an extra bonus of cleverness & talent that this film seems to surprise us with at every turn. Seriously, these songs are as good or better than the movie.

But at the end of the day, Always Be My Maybe is a carefully crafted & deeply entertaining take on When Harry Met Sally that Wong & Park have developed for several years even before the cameras came on and it shows. The chemistry between long-time friends is apparent and the several layers of thought in its cast & plot construction make this one of the better rom-coms in recent years on Netflix or otherwise.

To All The Boys I've Loved Before

Director: Susan Johnson
Cast: Lana Condor, Noah Centineo, Anna Catchcart, John Corbett, Andrew Bachelor
Rated: TV-14

Picture: Netflix

Behind only the ultra-violent extravaganza that is the Chris Hemsworth-led Extraction films, the To All The Boys YA rom-com trilogy is one of the best franchises in Netflix history and possibly the most important, alongside its fellow YA rom-com trilogy peers, The Kissing Booth franchise.

Based on the 2014 novel of the same name by Jenny Han, To All The Boys I’ve Loved Before was the crown jewel for Netflix in their “Summer of Love” series of films in 2018 that saw a reported 80 million subscribers flock to those films over that span. The film kicked off not only the aforementioned trilogy of films, but also the series spin-off “XO Kitty” for co-star Anna Cathcart who plays the younger sister in the films.

The first film (and best one in the franchise only slightly ahead of Always and Forever IMO) tells the story of Lara Jean Covey (played by X-Men: Apocalypse co-star Lana Condor), a shy yet smart high school junior, who has written a series of letters over her formative years to “boys she has loved before” (duh) which have been locked away in her closet never to be seen by anyone. When Lara Jean’s younger sister Kitty finds the letters and sends them out to her secret admirers, she is confronted by several of them the following day in school: classmate/nemisis Peter Kavinsky (Noah Centineo), her friend & sister’s boyfriend Josh (Happy Death Day franchise co-star Israel Broussard), & former crush/current gay friend Lucas.

When Peter tells Lara Jean about the letter, she faints at the thought. Upon awakening, she sees Josh holding his letter and heading in her direction. In a panic, Lara Jean kisses Peter to make Josh jealous & confused enough to walk away. Later, Peter tracks Lara Jean down at her favorite diner where she explains her situation with Josh and how the kiss was a ruse to ward him off. Inspired by this, Peter proposes the two of them fake a relationship in order to make Josh and Peter’s ex-girlfriend Gen (“Riverdale” co-star Emilija Baranac) jealous of their new love and maybe tempt them into reuniting.

In classic rom-com fashion, what starts as fake gets more and more real just as their real plan starts to work. Now facing a true crisis of the heart, Lara Jean must find herself in order to do what’s best for her future.

To All The Boys I’ve Loved Before launched the careers of its leads Lana Condor & Noah Centineo, and for good reason. Their chemistry sells the story and helps rise about the inevitable conclusions & cliches of the genre; a chemistry that made a trilogy out of their story in a genre that rarely gets the pleasure of that development. Not only that, but the movies continue with the spin-off series XO, Kitty, heading into its second season.

With that chemistry at the center of the frame, it may be easy to overlook what may be the real reason for its success: the family. The close bond between the sisters, the struggle of losing their mother, & the sensitivity and warmth of the father left behind really grounds the film and makes the setting more inviting for its audience.

To All The Boys I’ve Loved Before may seem like an obvious choice for this list because of its larger franchise success, but it’s more obvious for its lived-in appeal and genuine charm. Many YA rom-coms happened around this time and in subsequent years, but this film rises above the field.

Love at First Sight

Director: Vanessa Caswill
Cast: Haley Lu Richardson, Ben Hardy, Rob Delaney, Jameela Jamil
Rated: PG-13

Picture: Netflix

Based on the beloved 2013 book “The Statistical Probability of Love at First Sight” by author Jennifer E. Smith, Love At First Sight is written by the absolutely delightful Katie Lovejoy who struck gold with her first produced film screenplay for To All The Boys: Always and Forever. Add in “Little Women” mini-series director Vanessa Caswill to helm the project and VIOLA, you have successfully raised the floor and given yourself a higher probability *wink* at rom-com success.

The film follows two university students, Hadley Sullivan & Oliver Jones, as they begin to fall for each other on their flight from New York to London. But as the chaos of a London airport, a perpetually dying cell phone, & previous engagements on opposite sides of the city start to turn the odds of reuniting against them, love – and a little London magic – may have a way of defying the odds.

Love at First Sight features an exceptionally deep cast featuring Edge of Seventeen & White Lotus standout Haley Lu Richardson as Hadley and X-Men: Apocalypse & Netflix’s 6 Underground star Ben Hardy as Oliver. The film also stars Catastrophe star & former Twitter lord Rob Delaney, Bridget Jones co-star Sally Phillips, actor/director Dexter Fletcher, and The Good Place actress Jameela Jamil as the chameleon-like narrator.

The result is a charming, yet heartstring pulling story that feels as lived in as Haley Lu’s airplane cardigan attire. The chemistry between Richardson & Hardy will make you forget how magically improbable certain parts of their budding romance are or how quickly things come together. Director Vanessa Caswill never rushes a moment between them as the film stays at cruising pace for much of its duration. Choices in mood & tempo such as these allow for a deeper, more realistic bond between its characters and the beautiful, bittersweet moments that transpire further into the London storyline.

So much of the story and its key takeaways are brought back to the core tenet of Hadley’s outlook on love & relationships: someone to hold your hand through life. Oliver’s parents have each other even when the light gets dark. Oliver has Hadley to guide him through his family’s impending heartbreak and Hadley has Oliver to guide her through her complicated feelings after her parents’ divorce and new marriage. It’s a simple, relatable theme that makes the story worth watching.

Overall, Love at First Sight is less about one true love and more about what love can give us as we navigate our lives. A well paced, well cared for film that never loses sight of what truly matters. It’s not flashy or busy like most streaming rom-coms and that’s a good thing. Quality casting gives birth to great chemistry and deeply rooted characters. Easily the best love story for Netflix in 2023 and the best in the last few years.

Set It Up

Director: Claire Scanlon
Cast: Zoey Deutch, Glen Powell, Taye Diggs, Lucy Liu
Rated: TV-14

Picture: Netflix

Top Gun: Maverick, Devotion, Anyone But You.

The current run for newly arrived superstar Glen Powell is very impressive and has cemented his place as a leading man of the future in Hollywood.

But the real ones know that Glen Powell has had his powers all along. Whether you started with him as far back as 2014’s Expendables 3 or his breakout 2016 with Hidden Figures & Everybody Wants Some!!, everyone who saw him knew what was to come.

My introduction to Glen Powell was in 2018 for our #2 film (which could be argued for #1) Set It Up, a film as much about the gambit of getting two bosses romantically involved as it is about why in God’s name would anyone consider throwing away a relationship with either Powell or his massively adorable co-star Zoey Deutch, who herself was coming in hot off of her bigger role in Everybody Wants Some!! as well as her starring role in Why Him? and Ed Sheeran’s romantic interest in the video for “Perfect”.

Written by Booksmart scribe Katie Silberman, the plot is as simple & evergreen as any rom-com could get: Two young assistants in New York City, Harper & Charlie, realize they can make their lives easier by setting up their workaholic bosses to date. While trying to perpetuate this romantic ruse between their nightmare bosses, the assistants realize they themselves might actually be right for each other. In other words, they “Parent Trap” their bosses and fall for each other in the process.

While the basic framework of the film may be a tad ordinary, the cast, setting, & snappy pacing make this a delight start to finish. With former castmates of Everybody Wants Some!! in the leads teaming with amazing chemistry & familiarity, the rest of the casting would need to keep pace and it absolutely does. Buzzy “SNL” star Pete Davidson is hilarious as Charlie’s roommate, “Unbreakable Kimmy Schmidt” standout Titus Burgess plays “Creepy Tim” (and he loves it), & comedian Leonard Ouzts steals the elevator scene as the freaked out UPS guy. Of course, Taye Diggs & Lucy Liu also kill it as the uptight, overbearing bosses that get matched together. The New York City setting is perfect as they whip around the capital city of industry making appearances & plot devices around city staples like Yankee Stadium. The pacing & editing match the tone of the hustle bustle our characters work in every day as well as the urgency of the “set-ups” they devise throughout the film.

Simply put, this film is just so much fun. It’s no mistake that the careers of the young cast and the brilliant minds who created such a delight have gone on to great things or at minimum a sustained veteran presence in the industry. All you “new to Glen Powell” fans need to put this one on your watchlist ASAP.

The Half Of It

Director: Alice Wu
Cast: Leah Lewis, Daniel Diemer, Alexxis Lemire, Collin Chou
Rated: PG-13

Picture: Netflix

Much like Set It Up, our #1 movie takes an old idea and makes it new. One of the many movies to loosely base itself on the classic 19th century play “Cyrano de Bergerac”, The Half of It takes the bones of the play’s story and makes a modern, yet evergreen retelling with a Queer character protagonist.

Written & Directed by Alice Wu, the film focuses on loner high school student Ellie Chu who lives in the remote town of Squahamish with her widowed father. She is known in her school for making extra money writing homework assignments for her fellow classmates, but inarticulate football player Paul Munsky has a different type of assignment in mind: write a series of letters & texts to his crush Aster Flores pretending to be a better version of Paul to win her affections. While reluctant at first, Ellie agrees to help Paul because her family is falling on hard times financially and barely being able to keep the lights on.

While fulfilling her obligations to Paul, the two become close and spend a lot of time together. While Paul is confused as to whether he actually should be with Ellie, Ellie develops feelings for Aster Flores. The entanglements of coming out, rejecting a friend’s advances, and hurting his own chances with someone else make this a compelling modern spin on the classic setup.

Honored with the Best Narrative Feature prize at the Tribeca Film Festival along with a Best Screenplay nomination at the 2021 Independent Spirit Awards, The Half of It became a critical darling for Alice Wu, who’s personal story partially mirrors Ellie’s tale as Wu herself did not come out to herself and others until she attended college at Stanford.

The film’s best parts are embedded in the depth & maturity of Ellie’s self-realization. She has to accept who she is as an intelligent & accomplished talent that needs to spread her wings outside of her small town just as much as she needs to figure out who and how she will love in her present & future. She also has the added guilt of being in an immigrant family that has lost their mother and feels obligated to help her broken father get by. Wu’s screenplay, full of relatable characters, small-town trappings, coming-of-age struggles, family warmth, & surprisingly effective humor, made this film stand out at the perfect time with the world stuck in Covid isolation in May 2021.