The 17 Best Romantic Comedies on Amazon Prime

8. Appropriate BehaviorYear: 2014
Director: Desiree Akhavan
Stars: Desiree Akhavan, Rebecca Henderson, Halley Feiffer
Rating: PG
Runtime: 86 minutes

Watch on Amazon Prime

By default, being a twenty-something is messy—whether it’s dealing with crumbling relationships, jobs you’re too inexperienced for or the lies you tell to appease your parents. Desiree Akhavan explores that universal experience of untangling our identities in 2014’s Appropriate Behavior. Shirin (Akhavan) is a secretly bisexual woman fresh out of a break-up and dedicated to getting ?over her ex-girlfriend. But Shirin’s dispirited attempts to push every aspect of her life back on track fall awkwardly and disappointingly flat at every turn. Shirin can talk her way into a job and a date, but can she keep either? Appropriate Behavior follow one woman’s journey through life telling everyone she’s an adult … until she accidentally becomes one. Rather deftly, Akhavan’s film serves as a commentary on translation—the differences between the language we use, the things we actually mean, and how it all gets twisted. The narrative plays with Shirin’s identities—as an Iranian, a woman, a millennial and a bisexual—sometimes hilariously, other times rather poignantly. All 86 minutes of the film are spent watching Akhavan’s character desperately and unsuccessfully try to say what she wants. But as the responsibilities, one-night stands and brushes with her ex mount, Shirin begins to realize that the real trick to communication is taking the time to understand yourself before trying to communicate that to someone else. Appropriate Behavior is undoubtedly a comedy, but also a heartfelt look at how we learn to say what we mean and be who we are. —Abbey White

9. Something’s Gotta GiveYear: 2003
Director: Nancy Meyers
Stars: Jack Nicholson, Diane Keaton, Vanna Bonta, Keanu Reeves
Rating: PG-13
Runtime: 128 minutes

Watch on Amazon Prime

When you’ve got two giants of cinema exploring love later in life, you can expect great chemistry. That’s what happens with Jack Nicholson and Diane Keaton when the former breaks his streak of dating women in their twenties and falls for the mother of one of his girlfriends (Amanda Peet). With a soundtrack that spans genres and generations (Badly Drawn Boy, Jimmy Cliff, Paul Simon and Django Reinhardt, to name just a few), this Nancy Meyers joint is a worthwhile take on the opposites-attract rom-com. —Josh Jackson

10. WaitressYear: 2007
Director: Adrienne Shelly
Stars: Keri Russell, Nathan Fillion, Cheryl Hines
Rating: PG-13
Runtime: 107 minutes

Watch on Amazon Prime

Every bit as comforting as the delicious, candy-colored pies Keri Russell bakes in the film, Waitress is a honeyed little comedy that should speak to anyone who has ever felt stuck in a situation. And as good as Russell is, the film’s true star is its writer/director/co-star, the late Adrienne Shelly. Murdered before the film saw its release, his movie stands as a wonderfully bittersweet testament to her considerable talent. And now its legacy continues on with a Broadway adaptation. —Jeremy Medina

11. Love & FriendshipYear: 2016
Director: Whit Stillman
Stars: Kate Beckinsale, Chloe Sevigny, Xavier Samuel
Rating: PG
Runtime: 93 minutes

Watch on Amazon Prime

The title of Whit Stillman’s latest comedy may be Love & Friendship, but while both are certainly present in the film, other, more negative qualities also abound: deception, manipulation, even outright hatred. Underneath its elegant period-picture surface—most obviously evident in Benjamin Esdraffo’s Baroque-style orchestral score and Louise Matthew’s ornate art direction—lies a darker vision of humanity that gives the film more of an ironic kick than one might have anticipated from the outset. Still, the humor in Love & Friendship is hardly of the misanthropic sort. As always with Stillman, his view of the foibles of the bourgeois is unsparing yet ultimately empathetic. Which means that, even as Stillman works his way toward a happy ending of sorts, the film leaves a slightly bitter aftertaste—which is probably as it should be. Such honesty has always been a hallmark of Stillman’s cinema, and even if Love & Friendship feels like more of a confection than his other films, that frankness, thankfully, still remains. —Kenji Fujishima

12. I’ll See You in My DreamsYear: 2015
Director: Brett Haley
Stars: Blythe Danner, Sam Elliott, Martin Starr
Rating: PG-13
Runtime: 95 minutes

Watch on Amazon Prime

Picture this: You’ve been on your own for decades following the death of your spouse, your friends are all mostly enshrined in retirement community living and you’ve just been told that you have to put your pooch to sleep. In a less thoughtful movie, you’d be expected to fall into a traditional romance with a perfect stranger and validate your existence anew through wholesome late-stage monogamy. But Brett Haley’s I’ll See You in My Dreams has insight and empathy to spare, which combine with its casts considerable charms—especially those of Haley’s star, Blythe Danner—to make his film altogether different from other fare of its sort. Danner’s happily independent widow falls into a friendship with her pool boy (Martin Starr) and into courtship with the never-more-dashing Sam Elliot, but I’ll See You in My Dreams doesn’t condescend to its characters (or its viewers). Instead, it offers an organic, non-judgmental portrait of one woman choosing to reconnect with life. —Andy Crump

13. JeffreyYear: 1995
Director: Christopher Ashley
Stars: Steven Weber, Michael T. Weiss, Patrick Stewart
Rating: R
Runtime: 93 minutes

Watch on Amazon Prime

Based on a play of the same name, written by Paul Rudnick, this charming and witty little morsel tracks the efforts of its titular character (Stephen Weber) as he attempts, at the peak of the AIDS crisis, to avoid any and all relationships, sexual or otherwise. But when he finally does find a potential partner in the form of a cute HIV+ gent (Michael T. Weiss), Jeffrey’s flimsily built wall protecting him from the world starts to crumble. While it plays some very serious concerns for laughs, the film doesn’t shy away from the bitter reality of how many people had been taken away from the world due to AIDS. It also serves as a reminder of why seeking connection and affection in the faces of such trials is so important. Plus, as with all of Rudnick’s work, the film is filled with sharp, pithy dialogue, handled ably by a winning cast that includes some delightful supporting work from Sir Patrick Stewart, Nathan Lane and future Mad Men cast member Bryan Batt. —Robert Ham

14. Dilwale Dulhaniya Le JayengeYear: 1995
Director: Aditya Chopra
Stars: Shahrukh Khan, Kajol, Amrish Puri
Rating: PG-13
Runtime: 188 minutes

Watch on Amazon Prime

Usually referred to simply as DDLJ, this movie is credited to have started Shah Rukh Khan on his path to eventual superstardom. Even today, Bollywood actresses tend to play second fiddle to their male counterparts, so Kajol (who goes by her first name) never quite got the same glory. Nevertheless, it’s fair to say that DDLJ changed the game for Hindi rom-com films. Twenty years on, Bollywood films continue to invoke DDLJ as an epitome of romance, with young actors trying to recreate their own versions of Raj and Simran. Set partially in London and partially in Punjab, India, DDLJ was one of the first films to specifically target an Indian diasporic audience with a story that stays true to Indian traditions such as respect for your elders, while also advocating young lovers to follow their heart. A win-win situation! Raj and Simran accidentally meet on a train trip across Europe. After a couple of cute confrontations, sparks fly between the two. But Simran’s father has promised her hand to a friend’s son in Punjab. On overhearing his daughter’s love for Raj, he flies in a rage and immediately packs the family bags for a flight to India and a quick wedding. Raj follows Simran with the intent to ask her father for Simran’s hand in marriage. He befriends the prospective groom, and slowly wins over all the family members with his shenanigans. But will he be able to convince Simran’s strict father? A hit soundtrack, lovely visuals of India and abroad, and a leading couple that charmed their way into its audiences, all contribute to DDLJ being included in all sorts of Bollywood lists. —Aparita Bhandari

15. PricelessYear: 2008
Director: Pierre Salvadori
Stars: Audrey Tautou, Gad Elmaleh, Marie-Christine Adam
Rating: PG-13
Runtime: 105 minutes

Watch on Amazon Prime

In Priceless (often compared to Breakfast at Tiffany’s), Audrey Tautou plays Irène—the most beautiful, dangerous and unapologetic gold digger in the French Riviera. Her best-laid plans begin to go awry as she develops feelings for a man of average means. Rather than date him, she trains him to become an “opportunist” instead. In true rom-com fashion, a series of ridiculous scenes unfold with an important lesson in how-to-get-what-you-want-from-the-opposite-sex: “Not finishing your sentences—as if it pains you too much to go on,” she firmly advises, “is extremely effective.” Irène has little depth, and the same could be said about the film, but it’s pretty obvious that that’s the point. Tautou is such an authentic, Gucci-wearing, femme fatale that it’s difficult to simply loathe her. She is, as usual, sincere in her delivery—even when she is delivering a sincerely superficial character. She also plays an amazingly convincing drunk, which some of the best actresses of our day (ahem, Kate Winslet, ahem) have been unable to accomplish. —Shannon M. Houston

16. CharadeYear: 1963
Director: Stanley Donen
Stars: Aubrey Hepburn, Cary Grant
Rating: NR
Runtime: 113 minutes

Watch on Amazon Prime

Cary Grant is the most charming male lead ever. Audrey Hepburn is the most charming female lead ever. Everything else is just bonus in this romantic thriller about a woman pursued in Paris for her late husband’s stolen fortune: the Henry Mancini score, the Hitchcock-ian suspense, the plot twists and Walter Mathau as a CIA agent. It’s a screwball comedy and an international spy thriller, and works equally as both. —Michael Dunaway

17. My Man GodfreyYear: 1936
Director: Gregory La Cava
Stars: William Powell, Carole Lombard
Rating: 13+
Runtime: 94 minutes

Watch on Amazon Prime

Gregory La Cava’s My Man Godfrey is kind of like a proto-Le Dîner de Cons—or Dinner for Schmucks—except that My Man Godfrey is really good and neither the latter nor the former film measure up to it. (Because Le Dîner de Cons is coarse, condescending trash, too.) La Cava’s inroads to skewering the upper crust is through the upper crust itself: The film takes its outsider protagonist, Godfrey “Smith” Parke (William Powell), who’s not an outsider at all but a man in exile from high society’s bosom, and inserts him into circumstances where he’s the sanest, sharpest man in the room. Rich people are wild. That’s the film’s subtext, or just its text, because Godfrey’s charges, the members of the family Bullock, are either completely out of their gourds or stuffed headfirst up their own asses. They’d have to be, perhaps, to mistake him for a vagrant when he’s actually a member of the elite class just like they are. They’d also have to be observant and considerably less self-absorbed to make these fine distinctions. La Cava has fun with the scenario, as does Powell, and as does the rest of the cast, in particular Carole Lombard, playing young Irene, who falls head over heels for Godfrey, blithely unconcerned with his disinterest, and Gail Patrick as the daffy Mrs. Bullock, full of unfettered, dizzying joy. Dizziness, of course, is a requirement. Films like My Man Godfrey, screwball joints that move at a laugh-a-minute pace, demand the exhaustion of their viewers, and La Cava wears us out as surely as he delights us. —Andy Crump