The 17 Best Romantic Comedies on Amazon Prime

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The 17 Best Romantic Comedies on Amazon Prime

Amazon has sevearl of the the best romantic comedies of all time free to stream for its Amazon Prime members, but you wouldn’t know it by browsing the site. Some of those films don’t show up until well after 20 pages of scrolling through some of the most vapid, poorly written excuses for rom-coms in the online giant’s massive catalog. But fear not, we’re here for you, digging through hundreds of films to find you the best romantic comedies.

The following movies range from a 1927 Buster Keaton classic silent film to more recent hilarious and heartening rom-coms like The Big Sick. There are Hollywood films and Bollywood films, indie movies and blockbusters. But all should have you laughing and feeling the love.

Here are the 17 best romantic comedies available to stream for free on Amazon Prime:

1. Rushmore

rushmore_poster.jpg Year: 1999
Director: Wes Anderson
Stars: Jason Schwartzman, Bill Murray, Olivia Williams
Rating: R
Runtime: 92 minutes

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Rushmore introduced the world to Jason Schwartzman and helped pivot Bill Murray’s career from broad comic to art-house juggernaut. An unlikely inter-generational love triangle leads to one of the most entertaining feuds in filmdom. Schwartzman’s Max Fischer is an ambitious yet academically underachieving student at the prestigious Rushmore Academy in Houston, and Bill Murray plays wealthy industrialist Herman Blume. The two strike up an unexpected and unconventional friendship, but both end up falling for Rosemary Cross (Olivia Williams), a teacher at Rushmore. When Max goes too far in trying to prove himself to Ms. Cross by breaking ground on a new building without the school’s permission, he’s finally expelled and ends up in a soul-crushing public school. To make matters worse, he finds out that Herman has begun dating the object of his desire. As with Bottle Rocket, Ruhsmore was co-written by Owen Wilson who, like Max, was expelled from a prep school. He and Anderson began work on the script long before Bottle Rocket was filmed, and Rushmore contains even more of the DNA found in the rest of Anderson’s catalog. Few films remain re-watchable into the double digits, but this one just keeps getting funnier.—Josh Jackson


2. The Big Sick

big-sick.jpg Year: 2017
Director: Michael Showalter
Stars: Kumail Nanjiani, Zoe Kazan, Holly Hunter
Rating: R
Runtime: 120 minutes

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The Big Sick can sometimes be awfully conventional, but among its key assets is its radiant view of its characters. Based on the first year in the relationship of married screenwriters Kumail Nanjiani and Emily V. Gordon, this indie rom-com has a mildly risky structure and some trenchant observations about the culture clashes that go on in immigrant families living in America. But what cuts deepest is just how profoundly lovable these people are. That’s not the same as being cutesy: Rather, The Big Sick is defiantly generous, understanding that people are horribly flawed but also capable of immeasurable graciousness when the situation requires. So even when the film stumbles, these characters hold you up. Nanjiani plays a lightly fictionalized version of his younger self, a struggling Chicago stand-up who is having as much success in his career as he in his dating life. Born into a Pakistani family who moved to the United States when he was a boy, he’s a dutiful son, despite lying about being a practicing Muslim and politely deflecting the attempts of his parents (Anupam Kher, Zenobia Shroff) to set him up in an arranged marriage. That’s when he meets Emily (Zoe Kazan), an American grad student with whom he’s instantly smitten. She swears she doesn’t want a relationship, but soon they fall for one another—even though Kumail knows it can’t work out. What’s most radical about The Big Sick is its optimistic insistence that a little niceness can make all the difference. —Tim Grierson


3. The General

the-general.jpg Year: 1926
Directors: Buster Keaton and Clyde Bruckham
Stars: Joseph Keaton, Marion Mack, Glen Cavender
Rating: NR
Runtime: 79 minutes

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When Yankee spies steal his locomotive and kidnap his girlfriend, a Southern railroad engineer ("The Great Stone Face" Buster Keaton) is forced to pursue his two beloveds across enemy lines. While a few Charlie Chaplin pictures give it a run for its money, The General is arguably the finest silent comedy ever made—if not the finest comedy ever made. At the pinnacle of Buster Keaton’s renowned career, the film didn’t receive critical or box-office success when released, but it has aged tremendously. It’s a spectacle of story, mishmashing romance, adventure, action (chases, fires, explosions) and comedy into a seamless silent masterpiece. —David Roark


4. His Girl Friday

his-girl-friday-poster.jpg Year: 1940
Director: Howard Hawks
Stars: Cary Grant, Rosalind Russell, Ralph Bellamy
Genre: Drama, Comedy
Rating: PG
Runtime: 92 minutes

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Special effects have become so sophisticated that many of us have probably forgotten how much pure amazement you can wreak with a great story and a script that doesn’t let up for one second. This amazing, dizzyingly paced screwball comedy by Howard Hawks stars Cary Grant and Rosalind Russell, and takes us back into two of the decade’s hallmark preoccupations: The “remarriage comedy” and the intrigue and obsessiveness of the newspaper world. The minute Russell’s Lindy Johnson stalks into the newspaper office run by her ex-husband Walter Burns (Grant), you know it’s to tell him she’s getting remarried and leaving journalism to raise a family, and you know that’s not how it’s going to end. No high-suspense mystery here. What puts you on the edge of your seat in this film is how you get there. Hilariously acted and expertly filmed, His Girl Friday derives much of its comedic impact from the incredibly clever and lightning-fast banter of the characters. Don’t even think about checking your phone while you’re watching this. In fact, try to blink as little as possible. —Amy Glynn


5. Sleepless in Seattle

sleepless-in-seattle-210.jpg Year: 1993
Director: Nora Ephron
Stars Tom Hanks, Meg Ryan, Bill Pullman
Rating: PG
Runtime: 105 minutes

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Sleepless in Seattle is essentially one giant love letter to 1957’s An Affair to Remember from writer/director Nora Ephron. Rita Wilson gives a memorable teary summary of the movie, and Annie (Meg Ryan) watches it before writing to Sam (Tom Hanks) inviting him to meet her at the top of the Empire State Building—the way Cary Grant and Deborah Kerr attempt to in their movie—on Valentine’s Day. When they finally meet on the observation deck, the theme from An Affair to Remember swells, setting the mood for anyone with an appreciation for good rom-coms. —Bonnie Stiernberg


6. The African Queen

the-african-queen-poster.jpg Year: 1952
Director: John Huston
Stars Humphrey Bogart, Katharine Hepburn, Robert Morley
Rating: NR
Runtime: 105 minutes

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The madcap, screwball comedies of the ‘30s and ‘40s helped set the template for the battle-of-the-sexes comedies that would populate American cinemas for years to come (and still do, to some extent). Writer/director John Huston’s genius in making The African Queen was taking the feuding couple out of the metropolitan areas for which they’d often been associated with and instead placing them square in the middle of an inhospitable jungle. With the added element of survival driving their journey, the flirtatious banter between classy widow Rose Sayer (Katherine Hepburn) and crass boatman Charlie Allnut (Humphrey Bogart) crackles all the more, making for a rom-com as vicious as it is sweet. —Mark Rozeman


7. Love Actually

love-actually.jpg Year: 2003
Director: Richard Curtis
Stars: Desiree Akhavan, Rebecca Henderson, Halley Feiffer
Rating: PG
Runtime: 86 minutes

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When it comes to portraying love confessions of all varieties, very few can beat the kind on display in Richard Curtis’ epic romantic comedy Love Actually. In one of the many romantic threads, Juliet (Keira Knightley), a recently married woman, has just discovered that her husband’s best friend Mark (Andrew Lincoln) has been nursing a secret crush on her. One night, he arrives at their front door and silently delivers his long repressed feelings via hand-drawn cue cards. While certainly sweet and heart-warming, the inherent sadness that pervades this scenario—such a relationship can never work out between the two—prevents the exchange from being overly saccharine. —Mark Rozeman


8. Appropriate Behavior

appropriate-behavior.jpg Year: 2014
Director: Desiree Akhavan
Stars: Desiree Akhavan, Rebecca Henderson, Halley Feiffer
Rating: PG
Runtime: 86 minutes

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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 Give

gotta-give.jpg Year: 2003
Director: Nancy Meyers
Stars: Jack Nicholson, Diane Keaton, Vanna Bonta, Keanu Reeves
Rating: PG-13
Runtime: 128 minutes

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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. Waitress

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

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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 & Friendship

love-friendship.jpg Year: 2016
Director: Whit Stillman
Stars: Kate Beckinsale, Chloe Sevigny, Xavier Samuel
Rating: PG
Runtime: 93 minutes

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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 Dreams

20-best-so-far-2015-Ill-See-You-in-my-Dreams2.jpg Year: 2015
Director: Brett Haley
Stars: Blythe Danner, Sam Elliott, Martin Starr
Rating: PG-13
Runtime: 95 minutes

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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. Jeffrey

jeffrey-210.jpg Year: 1995
Director: Christopher Ashley
Stars: Steven Weber, Michael T. Weiss, Patrick Stewart
Rating: R
Runtime: 93 minutes

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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 Jayenge

dilwale-210.jpg Year: 1995
Director: Aditya Chopra
Stars: Shahrukh Khan, Kajol, Amrish Puri
Rating: PG-13
Runtime: 188 minutes

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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. Priceless

priceless-210.jpg Year: 2008
Director: Pierre Salvadori
Stars: Audrey Tautou, Gad Elmaleh, Marie-Christine Adam
Rating: PG-13
Runtime: 105 minutes

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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. Charade

charade.jpg Year: 1963
Director: Stanley Donen
Stars: Aubrey Hepburn, Cary Grant
Rating: NR
Runtime: 113 minutes

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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 Godfrey

my-man-godfrey-criterion.jpg Year: 1936
Director: Gregory La Cava
Stars: William Powell, Carole Lombard
Rating: 13+
Runtime: 94 minutes

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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