The Best Romcoms Of The Past Decade

Even though romcoms may be steadily declining in interest for women, according to Business Insider, the past decade of the genre really presented some fun and meaningful installments. In particular, the wild success of more diverse love stories embodied by select films brought in fresh new perspectives that helped revitalize romcoms in interesting ways. 

While it feels like something of an oversight that everyone's boyfriend Keanu Reeves only appears in one of the most stellar romcoms of the last decade, there are still plenty of crushworthy stars in these features, including the likes of Ryan Gosling, George Clooney, and Taye Diggs — not to mention unsuspecting romantic leads like Chris O'Dowd and the late James Gandolfini — who stole our hearts along with those of their leading ladies. Involving snail mail meet-cutes and office romances, these romcoms are the best of the past decade. Let's hope we get more like them in the next one!

Based off of writer and star Kumail Nanjiani's strange real-life love story with his wife, Emily Gordon, who also co-wrote the film (via People), The Big Sick revolves around a young Pakistani American wannabe comedian Kumail whose conservative family has decided to arrange a marriage for him. That is, until he meets Emily (Zoe Kazan) and falls for her. Because of his parents' expectations that he'd marry a Desi American Muslim, Kumail keeps his relationship with Emily a secret until she finds out about all the various women with whom he's been set up. 

Things take a dark turn for this romcom when Emily is hospitalized with a mysterious illness, and, since Kumail was still listed as her emergency local contact, he ends up hanging out at the hospital with Emily's folks as they all inadvertently begin to get to know each other and bond. Spectrum Culture said, "The Big Sick is that rare film that reminds us, through both wry humor and understated poignancy, that life's most meaningful moments often occur when we veer off script."

"As Etta James might say: at last. A romantic comedy that is romantic and funny and not simply an insult to the intelligence of all carbon-based life forms," The Guardian wrote about Enough Said, a rare romcom that focuses on the trials and tribulations of two older single folks as they dive back into the dating pool. Starring James Gandolfini as Albert in his last screen role before his untimely death, alongside a much less happy-go-lucky Julia Louis-Dreyfus as Eva, Enough Said is as much about friendship as it is about love and romance. 

Eva is a traveling masseuse who does home visits all around Los Angeles, Calif. One of her clients Marianne (Catherine Keener) wants to build a friendship and invites Eva to a party, where she meets Albert. Little does Eva know, Marianne is Albert's ex-wife, and Eva gets caught in a bizarre family circle as her relationship with Albert progresses. 

About Gandolfini's beautiful last performance, The Telegraph wrote, "The film contains Gandolfini's final lead role, but his performance is cherishably un-final: easy, open and insisting on nothing, it's the work of a man who is just getting started." 

Based on Walter Kirn's darkly comedic novel, Up in the Air features George Clooney as anything but a straightforward romantic lead in his portrayal of Ryan Bingham, an adult lost boy who makes his living helping companies fire people more humanely while also attempting to be the youngest person to earn 10 million frequent flier miles with American Airlines. Ryan's home is up in the air since he travels so much that he doesn't bother keeping a permanent address anywhere. Then he meets a fellow frequent traveler Alex (Vera Farmiga) and begins to fall for her. 

Unfortunately for Ryan, Alex already has a husband and a family — her stolen moments with Ryan serve as an escape from her real life — which interestingly shifts Up in the Air from a romcom between adults to a story about Ryan coming to terms with himself and his relationship with his own choices, for better or worse. Bowling Green Daily News raved, "Jason Reitman raises the bar with a beautifully crafted film that is smart, topical, funny and just a little bittersweet. It's a perfect mix for a film that proves to be the very best of 2009," and also best of the decade to boot. 

We have streaming service Netflix to thank for To All the Boys I've Loved Before, a charming high school romcom that is also equal parts family drama and a thoughtful musing on the importance of sisterhood. After Lara Jean's (Lana Condor) beloved mother dies, she and her sisters pledge to have each others' backs, always. So when a stack of love letters Lara Jean wrote to boys she had crushes on actually gets mailed, including one to her older sister's ex-boyfriend Josh (Israel Broussard), Lara Jean scrambles to gain the upper hand in the disaster. 

She forges a fake relationship with one of the other boys she'd loved before, dreamy Peter Kavinsky (Noah Centineo) who wants to make his ex-girlfriend jealous too. As to be expected, nothing quite goes to plan when both Lara Jean and Peter start catching actual feelings for each other. "The film is precisely what it should be: pleasing and clever, comforting and fun and romantic," NPR wrote, forgetting to mention the wonderful chemistry between the entire cast of what's become one of the best romcoms on Netflix.

It's rare for a romcom to tackle heavy social issues like abortion, but thanks to Gillian Robespierre's compassionate writing and directing as well as Jenny Slate's fantastic comedic and dramatic timing, Obvious Child ends up accidentally creating a new sub-genre to powerful effect. After aspiring comedian Donna (Slate) has a drunken one-night stand with Max (Jake Lacy) that ends in her getting pregnant, she has two choices for termination dates: her mother's birthday or Valentine's Day. While she has doubts about the procedure, she also knows she's not ready to have a child, especially not alone.

In the meantime, Max has been looking for her and Donna feels she has no choice but to push him away until he comes to one of her comedy sets and she reveals her whole pregnancy fiasco to him and the entire audience. This movie has one of the most surprising and oddly heartwarming romcom endings of recent years and is sure to be a top choice for years to come.

Unlike many of the best romcoms of the past decade that broke the mold in different ways, Set It Up is an homage to peak '90s romances in the style of The Devil Wears Prada and She's All That. Harper (Zoey Deutch) and Charlie (Glen Powell) are overworked executive assistants to Manhattan powerhouses Kirsten (Lucy Liu) and Rick (Taye Diggs). After another day of being exploited by their demanding bosses, Harper and Charlie plot to set up them up in hopes that a relationship would give them breathing room from work. 

While Set it Up starts out a straightforward office romcom, the plot twists as Kirsten and Rick's relationship heats up while various manipulations continue to shape its development. By the end, several reversals of fortune take place and the couples who end up together aren't necessarily the ones viewers were expecting. Smash Cut Reviews wrote, "Set it Up is the perfect example of a broad romantic comedy done right. It adheres to the formula for the most part but isn't afraid to break it. It has its own style and moves to beat of its own drum."

You wouldn't think that a film starting with an announcement of infidelity and divorce would end up on a romantic comedy list, let alone as one of the best romcoms of the past decade, but, thanks to its stellar ensemble cast and strong writing, Crazy, Stupid, Love fits the bill. Cal Weaver (The Office's Steve Carrell) is devastated after finding out his partner since childhood, Emily (Julianne Moore), has cheated and wants to break up. Cal takes to loudly drowning his sorrows at a local watering hole where gorgeous playboy Jacob (Ryan Gosling) takes pity on him and teaches him how to pick up women. 

But Crazy, Stupid, Love is about much more than Cal's revenge hook-ups and failed meet-cutes. Uproxx mused, "The result is something that definitely has a very mainstream sensibility, but punctuated with some genuine observation, some honest insight into the way we all struggle towards what we think we want, and how we often lie to ourselves about what that is." As we uncover each the characters' links to each other, the result is equal parts heartwarming and heart-wrenching. And it's downright hilarious.  

While 500 Days of Summer has a typical will-they-or-won't-they romcom plot at first, where it stands apart from other films is its unique narrative structure that flips back and forth between past and present to detail the 500 turbulent days of Tom (Joseph Gordon-Levitt) and Summer's (Zooey Deschanel) relationship. Tom is an architect who has found himself stuck in a rut writing greeting cards rather than designing buildings as was once his dream. His dream gets deferred once again when manic pixie dream girl Summer comes into his life.

In a lovely romcom reversal of tropes, Tom believes in true love and that Summer is his, while Summer isn't sure she believes love exists at all, putting a clever spin on 500 Days of Summer that makes it a stand-out this past decade. Arizona Republic went so far as to call it "an unpredictable, immensely satisfying experience, much like love itself."

With the first all-Asian cast of an American romantic comedy making cinema history, Crazy Rich Asians isn't just one of the best romcoms of the past decade, but it's also a film that is poised to change Hollywood as a whole, at least according to Time. Bringing some much needed Asian representation to the romcom formula, Constance Wu plays professor Rachel Chu who agrees to visit boyfriend Nick's Singapore home for the wedding of his best friend. Little does Rachel know, Henry is basically Asian royalty and her New Yorker street smarts have nothing on the socialites in Henry's orbit, including his disapproving mother Eleanor (Michelle Yeoh). 

Den of Geeks raved, "Crazy Rich Asians is delightful and features an array of great performances. Funny yet inoffensive, sweet but not overly sentimental, it is one of the best rom-coms in recent years." By the numbers, Crazy Rich Asians also marked the highest-grossing romantic comedy in a decade, as HuffPost reported, proving once and for all that non-white casts are extremely capable of pulling in cinema audiences.

Chris Rock brought his comedic stylings to the romcom Top Five, which he also wrote and directed. Rock plays Andre Allen, a former comedian-turned-actor in a slapstick franchise where he plays a cop in a bear suit. Andre's romantic interest is entertainment journalist Chelsea (Rosario Dawson) who plans to do an in-depth interview of Andre's entire career. The two end up learning a lot more personal things about each other than they ever expected, including their shared struggles with alcoholism. 

While many of the themes in Top Five are deep and dark, the film's backdrop of New York's comedy scene, as well as a host of great cameos from famous comedians, keeps the film on its darkly comedic tracks, even as Andre and Chelsea's struggles with each other and themselves get more and more complicated. Spectrum Culture noted, "Top Five ... finally gives Rock the filmic vehicle he has needed since he tried to transition to the screen." His comedic chops are on display as usual, but he also displays an uncharacteristic vulnerability that brings a lot to the movie. 

Always Be My Maybe might be a love story between two estranged childhood best friends Sasha (Ali Wong) and Marcus (Randall Park) at heart, but it is also as much a love letter to San Francisco's Bay Area and the thriving arts culture featured as the backdrop to Sasha and Marcus' on-again, off-again relationship. Now a celebrity chef and living her best life, Sasha returns to her hometown to open a new restaurant and reconnects with Marcus, who is far from living his best life as an assistant at his dad's heating and air conditioning repair company. 

Sasha and Marcus revisit their past and dance around feelings for each other, until Sasha's new boyfriend Keanu Reeves — the actor plays a most absurd and pretentious version of himself — inadvertently forces their hands and their hearts back together. "It's a film that delivers on all its promises, gives a lot of funny people a chance to shine and — yes indeed — provides some much-needed representation to a lot of potential love-story leads who don't see themselves in Hollywood nearly often enough," NPR wrote.

A rarity in the romcom genre is getting any significant award nods for a movie in this style. But La La Land became one of the biggest exceptions to this rule by landing not only major BAFTA and Golden Globe nominations for best film and more, but it also received a whopping 14 Academy Award nominations — tying All About Eve and Titanic for most noms for a single movie, as reported by Entertainment Tonight — and took home awards for best director and best actress, among others. This makes La La Land not just one of the best romcoms of the past decade, but arguably also one of the best of all time thanks to its immense critical reception. 

Following two struggling Los Angeles artists, jazz pianist Sebastian (Ryan Gosling) and wannabe actress Mia (Emma Stone), La La Land pays beautiful tribute to the Hollywood musicals of olden days where it was just perfectly natural to all of a sudden break into a song and dance to move the narrative forward to an unexpected conclusion. Stone and Gosling did all their own singing and dancing to boot in this charming love letter to Old Hollywood. NPR gushed, "It's just gorgeous, like a flipbook made of dreamy vintage postcards that are somehow about contemporary life in Los Angeles."

You cannot have a list of the best romcoms from the past decade without at least one Queen Latifah vehicle in the mix. In Just Wright, Latifah plays Leslie, a basketball fan and physiotherapist who is on the lookout for love. She lives with Morgan (Paula Patton), a woman whose dream is to marry not for love, but for money, her eyes fixed on any NBA player who'll have her. Leslie meet-cutes basketball player Scott (Common) at a gas station, but her interest in the charming player is thwarted when Scott shows more interest in Morgan, proposing to her quickly. After Scott suffers an injury and needs physical therapy, Morgan suggests Leslie, thinking she is no threat to their engagement. 

As it turns out, Morgan was the threat to the engagement, though we'll let you learn just how she became her engagement's own undoing for yourself. The Washington Post raved (via Rotten Tomatoes), "Latifah and Common create something that's all too rare in contemporary romantic comedies, and that's the sense that their characters actually, you know, like each other." 

Yes, Bridesmaids is about a wedding and all the romcom hijinks that come along with this major life event. But Bridesmaids is also as much a platonic love story between two best friends whose relationship is shifting into uncharted territory on the eve of said wedding. Annie (Kristen Wiig) and Lillian (Maya Rudolph) have been besties for so long they are practically sisters. But this changes when Lillian announces she's getting married to her long-time beau, and Annie slowly begins having a very public — and also very funny — breakdown as she tries to process her sister-friend moving on to a new stage of life when she can barely pay her own bills. 

Bridesmaids is not only one of the best romcoms of the past decade, it's also unique in that most of the romantic male leads in the film take a sideline to the strange and hilarious cast of women who steal every scene they're in — from getting food poisoning on dress-fitting day to having a mid-flight meltdown for the ages. CineVue wrote, "Bridesmaids manages to take a seen-before storyline and turn it into something unpredictable, entertaining, and so completely wrong it feels right — and very satisfying."