Movies The 27 best romantic comedies on Max From romantic old Hollywood classics to hilarious new favorites, there's plenty to love about these titles on Max. By Ilana Gordon, Ilana Gordon Ilana Gordon is an entertainment, culture, and comedy writer originally from Connecticut. She currently lives in Los Angeles. EW's editorial guidelines Kevin Jacobsen, and James Mercadante Updated on December 13, 2024 05:42AM EST Forget kissing someone at midnight. If you're looking to fall in love from the comfort of your couch, Max has you covered. From screwball to Shakespeare, relationships come in many shapes and life stages, and these 27 Max favorites will carry you from meet cute to matrimony. And along the way, they'll show you how to live, laugh, and love in ways a sign from T.J. Maxx could never. 01 of 27 50/50 (2011) Joseph Gordon-Levitt and Seth Rogen in '50/50'. Chris Helcermanas-Benge/Summit Entertainment If you’re looking for a lighthearted, romantic romp, 50/50 is not the movie for you. Guaranteed to make you ugly cry and call your loved ones, this black comedy about falling in love in the middle of cancer treatment is beautifully written and acted, and has a lot to say about maternal, platonic, and romantic relationships. Joseph Gordon-Levitt stars opposite Seth Rogen, who also executive produces. (The script is based on screenwriter Will Reiser’s actual cancer battle, and the character of Kyle is based on Rogen, who is real-life friends with Reiser.) The film’s subject matter could have resulted in a saccharine sob-fest, but EW’s critic writes that the jokes and energy Rogen & Co. bring to the project helps evoke a “mash of the sweet and the bracingly coarse, that sells this unusual downer/upper of a life-and-death comedy.” —Ilana Gordon Where to watch 50/50: Max EW grade: B+ (read the review) Director: Jonathan Levine Cast: Joseph Gordon-Levitt, Seth Rogen, Anna Kendrick, Bryce Dallas Howard, Anjelica Huston Seth Rogen would like film critics to know that negative reviews 'hurt' and are 'devastating' 02 of 27 Amélie (2001) Audrey Tautou in 'Amélie'. Amelie: Bruno Calvo This French language romantic comedy tells the story of a Parisian waitress (Audrey Tautou) whose life takes on new purpose after she discovers a box of childhood treasures under a floorboard in her apartment and reunites them with their owner (Maurice Bénichou). A whimsical, playful film that charmed French moviegoers, international audiences, and critics alike, Amélie the character ends up having much more depth than her Manic Pixie Dream Girl counterparts, and the movie itself is endlessly enjoyable. EW’s critic at the time writes, “While Amélie the plucky girl beguiles, Amélie the charming movie, already an international success, seduces.” —I.G. Where to watch Amélie: Max EW grade: N/A (read the review) Director: Jean-Pierre Jeunet Cast: Audrey Tautou, Mathieu Kassovitz, Rufus, Lorella Cravotta The biggest foreign film winners in Oscar history 03 of 27 Am I OK? (2022) Dakota Johnson in 'Am I OK?'. Everett A coming out and coming-of-middle-age movie co-directed by comics and real-life spouses Tig Notaro and Stephanie Allynne, Am I Ok? is the queer millennial movie you didn’t know you needed. Dakota Johnson stars as Lucy, a woman stuck in career and romantic limbo, who is forced out of her everyday mundanity by a new understanding of her sexuality and her best friend’s upcoming international move. A comedy about love — both platonic and romantic — the movie was filmed during the pandemic and premiered at Sundance, but has since found a home on Max, and a fan base amongst movie lovers who enjoy authentic comedies about late bloomers finding love and themselves. —I.G. Where to watch Am I OK?: Max Directors: Tig Notaro, Stephanie Allynne Cast: Dakota Johnson, Sonoya Mizuno, Jermaine Fowler, Kiersey Clemons, Molly Gordon, Whitmer Thomas, Odessa A'zion, Sean Hayes, Tig Notaro Dakota Johnson jokes she 'made out with a lot of women during Covid' to practice for Am I Ok? 04 of 27 As Good As It Gets (1998) Jack Nicholson and Helen Hunt in 'As Good As It Gets'. Everett As Good As It Gets is not interested in being your prototypical romantic comedy. The film scorns genre tropes and easy to digest characters in favor of following a selfish, misanthropic writer (Jack Nicholson), a struggling waitress (Helen Hunt), and a gay painter (Greg Kinnear), all of whom end up in each other’s lives after a series of unfortunate events. Released in the late ‘90s and offering a progressive exploration — at the time — into topics like sexuality and mental health, the film is well-regarded for its smart dialogue and winning performances. (Nicholson and Hunt both took home Best Acting Oscars for their work on the film.) As EW’s critic at the time writes, “it’s fun to watch Jack Nicholson draw on great reservoirs of bile to play a mean SOB with an obsessive-compulsive disorder who is partially humanized by his contact with Helen Hunt (well, who wouldn’t be)?” —I.G. Where to watch As Good As It Gets: Max EW grade: B— (read the review) Director: James L. Brooks Cast: Jack Nicholson, Helen Hunt, Greg Kinnear, Cuba Gooding Jr., Skeet Ulrich, Shirley Knight The best Jack Nicholson performances 05 of 27 Baby Mama (2008) Tina Fey and Amy Poehler in 'Baby Mama'. Everett Collection Tina Fey and Amy Poehler have a chemistry that reads across sketches, stages, and screens, and it's on full display in Baby Mama. An Odd Couple-style comedy about surrogacy, the film finds executive Katie Holbrook (Fey) hiring Angie Ostrowski (Poehler), a wild card from South Philly, to carry her baby. As the two women wrestle with their personal incompatibilities — and Angie’s tendency towards con artistry — they find growth in themselves and a friendship with each other. EW’s critic at the time writes, “Poehler is as improv-sketch loose in her performance as Fey is measured, and both are challenged to a thespian throwdown by a fearsomely funny Sigourney Weaver as the smug head of the surrogacy agency.” The plot is fun, the acting is great, and both the comedy and babies in the film are delivered flawlessly. —I.G. Where to watch Baby Mama: Max EW grade: B (read the review) Director: Michael McCullers Cast: Tina Fey, Amy Poehler, Greg Kinnear, Dax Shepard, Romany Malco, Maura Tierney, Holland Taylor, Sigourney Weaver Tina Fey and Amy Poehler love to watch Saturday Night Live together: 'We root for everybody' 06 of 27 Bridget Jones's Diary (2001) Renée Zellweger in 'Bridget Jones's Diary'. Miramax/Everett When it comes to turn of the 21st century romantic comedies, you don’t get much more iconic than Bridget Jones’s Diary. Based on the novel by Helen Fielding, Bridget Jones tells the story of its eponymous heroine, Bridget (Renée Zellweger), a British thirtysomething looking for love. Bridget’s romantic life — which she chronicles in her diary along with her other misadventures — takes a turn when she engages in an ill-fated affair with her dashing boss, Daniel Cleaver (Hugh Grant), leaving the kind Mark Darcy (Colin Firth) in the lurch. Fans of the book were skeptical when production announced the role of Bridget would be played by a Texas-born actress, but Zellweger pulls off the role with aplomb, perfectly channeling Bridget’s lovably messy essence. —I.G. Where to watch Bridget Jones’s Diary: Max EW grade: N/A (read the review) Director: Sharon Maguire Cast: Renée Zellweger, Colin Firth, Hugh Grant, Jim Broadbent, Gemma Jones Hugh Grant rewrote his part in Bridget Jones 4 before joining the cast 07 of 27 Casablanca (1942) Humphrey Bogart and Ingrid Bergman in 'Casablanca'. Everett Collection Despite boasting some of the best quotes in all of cinematic history, Casablanca was just one of many films churned out by the studio system in the early years of World War II. But something about the movie's heart-wrenching love triangle, political and social relevance, and lush setting charmed viewers, propelling the project to an unexpected Best Picture win, and a permanent spot on almost every Best Of list. Electricity rations were common at the time of the movie's release, but entirely unnecessary — the sexual currents pulsating between stars Humphrey Bogart and Ingrid Bergman had to have been strong enough to generate power for a small city, at the very least. —I.G. Where to watch Casablanca: Max EW grade: A (read the review) Director: Michael Curtiz Cast: Humphrey Bogart, Ingrid Bergman, Paul Henreid, Claude Rains Casablanca live-read will turn the classic film into a lesbian love story 08 of 27 Dear White People (2014) The cast of 'Dear White People'. Lara Solanki/Netflix When the movie Dear White People was released in 2014, it represented a step for modern cinema: an ensemble movie about a group of Black students at a fictional, predominantly white university, as told from the perspective of those Black students. Featuring one of Tessa Thompson's breakout movie roles, Dear White People was a critical and commercial success, spawning a TV series of the same name in 2017, which ran for four seasons on Netflix. While this isn’t a romantic comedy by traditional definitions, it's definitely a comedy and the students’ love lives all play significant and interesting roles. You may recognize some of the film’s jokes from screenwriter and director Justin Simien’s Twitter (now X) account circa the early 2010s, where the writer used to workshop some of the film’s future material. —I.G. Where to watch Dear White People: Max Director: Justin Simien Cast: Tessa Thompson, Tyler James Williams, Teyonah Parris Is Netflix's Dear White People as good as the movie that inspired it? 09 of 27 The Devil Wears Prada (2006) Anne Hathaway in 'The Devil Wears Prada'. 20th Century Fox/Courtesy Everett Collection Meryl Streep may not have won the Oscar for her performance as Miranda Priestly in The Devil Wears Prada, but the film does bear the distinction of being one of her most quotable works. An adaptation of the 2003 novel by the same name — which was based on the author’s experiences working as an assistant at Vogue — the movie tells the story of Andy Sachs (Anne Hathaway), an aspiring writer who accepts a job working for the demanding editor in chief at one of the most distinguished fashion magazines in New York City. What follows is a headlong descent into the fashion world, complete with ridiculous assignments, eccentric characters, and glorious outfits. Hathaway is charming as the fish out of water who gets the fashion education she never knew she wanted or needed, but the movie belongs to Streep and her clipped, precise performance. That’s all. —I.G. Where to watch The Devil Wears Prada: Max EW grade: N/A (read the review) Director: David Frankel Cast: Meryl Streep, Anne Hathaway, Emily Blunt, Stanley Tucci, Simon Baker, Adrian Grenier Devil Wears Prada producer recalls being told Meryl Streep has 'never been funny a day in her life' 10 of 27 Dinner With Friends (2001) (From left to right) Toni Collette, Dennis Quaid, Greg Kinnear, and Andie MacDowell in 'Dinner With Friends'. Everett HBO's cinematic adaptation of Donald Margulies' Pulitzer Prize winning 1998 play, Dinner With Friends maintains the original's simple premise while mining deep for emotional and personal revelations. The story of two New England couples dealing with the fact that one of the pairs is divorcing, the film captures the unexpected moments of vulnerability and honesty that define long-term relationships — even ones that are falling apart. Dennis Quaid and Andie MacDowell are perfectly cast as a pair of foodies who are more comfortable navigating what's on their dinner plates than what's going on in their friends' lives, and Greg Kinnear and Toni Collette toggle between insecurity and self-assurance as the couple whose marriage is broken up by an affair with a younger woman. Haute cuisine served over seven scenes, Dinner With Friends is the rare adaptation that remains faithful to the original while still finding new paths to tread. —I.G. Where to watch Dinner With Friends: Max EW grade: N/A (read the review) Director: Norman Jewison Cast: Dennis Quaid, Andie MacDowell, Greg Kinnear, Toni Collette The 18 best romantic comedy movies on Netflix 11 of 27 Fever Pitch (2005) Drew Barrymore and Jimmy Fallon in 'Fever Pitch'. Everett Collection The only film to feature a love triangle between a woman, a man, and the baseball team he adores, Fever Pitch bears the distinction of not only being a solid romantic comedy, but of also doing its part to help break an 86-year-old curse. Ben (Jimmy Fallon) is a Red Sox superfan who falls in love with a baseball agnostic named Lindsey (Drew Barrymore), but struggles to prioritize their relationship over his MLB viewing schedule. The movie was filmed during the 2004 Red Sox season, which — not to drop any spoilers two decades later — ended up being an eventful one for Boston, necessitating a rewrite for the movie’s ending. You don’t need to love baseball to enjoy this sports comedy, but it doesn’t hurt to have an appetite for New England-based humor, super fandom, and underdog stories. —I.G. Where to watch Fever Pitch: Max EW grade: N/A (read the review) Directors: Peter Farrelly, Bobby Farrelly Cast: Drew Barrymore, Jimmy Fallon The 11 wicked best Boston movies 12 of 27 Forgetting Sarah Marshall (2008) Mila Kunis and Jason Segel in 'Forgetting Sarah Marshall'. Universal/Everett Jason Segel bares his soul — and his fully nude body — in Forgetting Sarah Marshall, a rom-com about a man trying to escape the aftermath of a bad breakup. Segel plays Peter, an aspiring composer who flees to a Hawaiian resort after being dumped by Sarah (Kristen Bell), a Hollywood TV star with bigger ambitions for her career and love life. Peter's island getaway takes a turn for the worse when Sarah and her new boyfriend show up to stay in the same resort, and it's further complicated when Peter starts to develop feelings for Rachel (Mila Kunis), the resort's receptionist. A comedy that allows you to romp through Hawaii's scenic vistas while unpacking a former couple's dirty laundry, Forgetting Sarah Marshall is a trip that will make you grateful you checked your own emotional baggage at the door. —I.G.Where to watch Forgetting Sarah Marshall: MaxEW grade: B+ (read the review)Director: Nicholas StollerCast: Jason Segel, Kristen Bell, Mila Kunis, Russell Brand, Bill Hader, Jonah Hill, Da'Vone McDonald, Jack McBrayer, Maria Thayer, Paul Rudd, Jason Bateman Muppet of a man: Watch Jason Segel revive his Dracula puppet musical from Forgetting Sarah Marshall 13 of 27 /Four Weddings and a Funeral (2008) Hugh Grant and Andie MacDowell in 'Four Weddings and a Funeral'. Gramercy Pictures/Courtesy Everett Collection No situation forces you to examine your life quite in the same way as a wedding or a funeral, and during Four Weddings and a Funeral, Charles (Hugh Grant) attends — as advertised — five of these events. The film picks up during the first wedding, where Charles meets an American woman named Carrie (Andie MacDowell); he then proceeds to spend the subsequent three weddings and one funeral trying to deduce how he feels about her. Surrounded by a group of friends navigating similar shifts in life and love, Charles must learn to overcome his fear of commitment, or risk losing the best thing that’s ever happened to him. “Weddings have rarely been choreographed so appealingly as they are in this creation from writer Richard Curtis and director Mike Newell,” writes EW’s critic. “And Grant is the rare actor who can mix the characteristics of sex appeal and ambivalence in believable, rather than irritating, proportions.” If you’re in the mood to enjoy romantic hijinks, statement hats, and self-deprecating British humor, RSVP yes to Four Weddings and a Funeral. —I.G. Where to watch Four Weddings and a Funeral: Max EW grade: A– (read the review) Director: Mike Newell Cast: Hugh Grant, Andie MacDowell, Kristin Scott Thomas, Simon Callow, James Fleet, John Hannah, Charlotte Coleman, David Bower, Corin Redgrave, Rowan Atkinson Hugh Grant jokes that he looks like 'a scrotum' in Oscars Four Weddings reunion with Andie MacDowell 14 of 27 Garden State (2004) Zach Braff and Natalie Portman in 'Garden State'. Everett Zach Braff's Garden State — the story of a struggling young actor's return home to New Jersey after the death of his mother — is not a perfect movie. Written by Braff during a period of depression and inspired by his own feelings of numbness, the film interrogates themes like mental illness, medication, growing up, and falling in love, sometimes nailing the sentiments and other times falling short. In spite of its deficits, however, the romantic comedy was a sleeper hit when it premiered in 2004, a reception attributable to the film's excellent soundtrack, objectively sick cast, and resonance with a young generation staring down the barrel of adulthood. Starring Braff as the film's protagonist and Natalie Portman as his eccentric and compulsively dishonest love interest, the film is often compared to The Graduate, but remains a singular romantic comedy that demands an emotional reaction from its audience. —I.G. Where to watch Garden State: Max EW grade: N/A (read the review) Director: Zach Braff Cast: Zach Braff, Natalie Portman, Peter Sarsgaard, Ian Holm, Jean Smart, Jackie Hoffman, Ann Dowd, Method Man, Jim Parsons Every song on the Garden State soundtrack, ranked 15 of 27 The Invention of Lying (2009) Ricky Gervais in 'The Invention of Lying'. Sam Urdank/Warner Bros./Courtesy Everett Collection In a world where everyone is compelled to tell the truth, one brave soul discovers his own ability to lie. This is the story of Mark Bellison (Ricky Gervais), a struggling screenwriter whose career, romantic prospects, and bank balance have never been lower. Enter: an epiphany. Mark discovers that only he has the power to mislead, and in so doing, opens up a world of possibilities for himself. A high-concept romantic comedy that is both ethically intriguing and deeply funny, The Invention of Lying is Gervais’ feature directorial debut. Though the visual aspects of the movie are not its strong suit, the premise, comedy, and performances are excellent, with EW’s critic at the time writing that the “jolting philosophical comedy The Invention of Lying is seriously subversive.” —I.G.Where to watch The Invention of Lying: Max EW grade: B+ (read the review) Directors: Ricky Gervais, Matthew Robinson Cast: Ricky Gervais, Jennifer Garner, Jonah Hill, Louis C.K., Jeffrey Tambor, Fionnula Flanagan, Rob Lowe, Tina Fey Ricky Gervais mourns the death of The Office costar Ewen MacIntosh: 'An absolute original' 16 of 27 The Last of the Blonde Bombshells (2000) Billie Whitelaw and Judi Dench in 'The Last of the Blonde Bombshells'. HBO/Everett A film with a sensibility that can only be described as singularly British, The Last of the Blonde Bombshells is a romantic comedy with some rhythm. Elizabeth (Judi Dench) spent World War II playing saxophone in a swing band called the Blonde Bombshells. After the death of her husband, Elizabeth reconnects with Patrick (Ian Holm) — the band's former drummer and only male member, who avoided conscription during the war by cross-dressing. When the pair start dating, Elizabeth decides to get the band back together, but discovers the Bombshells have scattered with members in jail, suffering from alcoholism, and devoted to the Salvation Army. Described by EW's reviewer as "witty and wistful," The Last of the Blonde Bombshells is another piece of evidence that blondes really do have more fun. —I.G. Where to watch The Last of the Blonde Bombshells: Max EW grade: B+ (read the review) Director: Gillies MacKinnon Cast: Judi Dench, Ian Holm, Romola Garai, Olympia Dukakis Judi Dench says acting 'has become impossible' due to worsening eyesight 17 of 27 Let Them All Talk (2020) Meryl Streep in 'Let Them All Talk'. HBO Max Joan Didion once said "Writers are always selling someone out," and that is exactly what Pulitzer Prize-winning author Alice Hughes (Meryl Streep) is accused of doing. In Let Them All Talk, Alice boards the Queen Mary 2 on a transatlantic trip with the intention of writing her new book and spending time with two of her oldest friends (Candice Bergen and Dianne Wiest). But as the voyage proceeds, Alice ends up battling with Roberta (Bergen) over how much of her original book was based on Roberta's life, and watching as her nephew Tyler (Lucas Hedges) falls for her literary agent, Karen (Gemma Chan). Funny, wise, bitter, primarily improvised, and made in barely two weeks, EW's critic describes the film as "a chance to spend two hours watching Streep & Co. make the most of Deborah Eisenberg's deliciously salty script, while Soderbergh — who also serves as cinematographer — shoots it all in ruthless, radiant light." —I.G. Where to watch Let Them All Talk: Max EW grade: A– (read the review) Director: Steven Soderbergh Cast: Meryl Streep, Candice Bergen, Dianne Wiest, Gemma Chan, Lucas Hedges, How Candice Bergen prepared for her Oscar-hopeful Let Them All Talk role 18 of 27 Mike and Dave Need Wedding Dates (2016) Aubrey Plaza, Anna Kendrick, Adam DeVine, and Zac Efron in 'Mike and Dave Need Wedding Dates'. Gemma LaMana/20thCentFox/Courtesy Everett Collection Combine Wedding Crashers and Neighbors and you get Mike and Dave Need Wedding Dates, a romantic comedy based on a true story and executed with a side of raucous raunch. Mike (Adam DeVine) and his brother Dave (Zac Efron) are elite partiers and their family has had enough of their antics. Concerned about how the two will act at their younger sister's Hawaiian wedding, their parents issue an ultimatum: Find some nice young women to bring as dates. The brothers put out a listing on Craigslist, it goes viral, and before long they've connected with Tatiana and Alice (Aubrey Plaza and Anna Kendrick), two degenerates cosplaying as innocents in the hopes of scoring a free Hawaiian getaway. What unfolds is a battle royale of bad behavior as the brothers and their dates do their best not to wreck the wedding. EW describes the film as "like riding a roller coaster fueled by Red Bull and grain alcohol: kind of gross but pretty fun, too." —I.G. Where to watch Mike and Dave Need Wedding Dates: Max EW grade: B (read the review) Director: Jake Szymanski Cast: Zac Efron, Anna Kendrick, Adam DeVine, Aubrey Plaza, Stephen Root The 15 best Zac Efron movies and TV shows, ranked 19 of 27 My Big Fat Greek Wedding (2002) John Corbett and Nia Vardalos in the first "My Big Fat Greek Wedding". Gold Circle Films Toula Portokalos (Nia Vardalos) embraces her role as the loyal yet overlooked member of her enormous clan until she decides to take control of her life at 30. While her parents tirelessly seek the perfect Greek man for her, Toula knows none of those suitors stand a chance against WASP English teacher Ian Miller (John Corbett), who's head over heels for her and is ready to take on the challenge of getting her family to approve their marriage. (He's really all that and a bottle of Windex!) Adapted from Vardalos' one-woman show based on her real-life family, My Big Fat Greek Wedding delves into the dynamics of growing up in an immigrant household deeply rooted in their culture, navigating a world that centers on conformity. —Angela Andaloro Where to watch My Big Fat Greek Wedding: Max EW grade: N/A (read the review) Director: Joel Zwick Cast: Nia Vardalos, John Corbett, Lainie Kazan, Michael Constantine, Gia Carides, Louis Mandylor, Andrea Martin, Joey Fatone Nia Vardalos directing My Big Fat Greek Wedding 3 in Greece: 'Much love and gratitude' 20 of 27 Pretty Woman (1990) Richard Gere and Julia Roberts in 'Pretty Woman'. Everett Collection If you haven't yet seen this '90s classic...big mistake! Big! Huge! Garry Marshall's Golden Globe-nominated flick spins a modern Cinderella story starring the then-rising star Julia Roberts as the unpolished, down-on-her-luck escort Vivian and Richard Gere as leverage buyout executive Edward, who offers her a taste of the high life in exchange for her company at social gatherings. While it's undeniably a product of its time, steeped in outdated gender stereotypes and degrading convictions of sex work, the film was groundbreaking during its initial release, and its enduring charm lies in the palpable chemistry between Gere and Roberts. Even EW's critic, who notoriously panned it with a D grade, had a change of heart 20 years later, bumping it to a B — acknowledging its message that "you can be a feminist and a seductress, a hooker and a princess, all at the same time" and how it "marked Pretty Woman as the rare Hollywood movie that doesn’t just channel the culture but changes it." —James Mercadante Where to watch Pretty Woman: Max EW grade: B (read the review) Director: Garry Marshall Cast: Julia Roberts, Richard Gere, Ralph Bellamy, Jason Alexander, Héctor Elizondo, Laura San Giacomo, Alex Hyde-White Makeover Magic: The secrets behind your favorite romantic comedy makeovers 21 of 27 Serendipity (2001) Kate Beckinsale and John Cusack in 'Serendipity'. Everett Collection When destiny has a sense of humor, we call it serendipity, which also happens to be the title of one of 2001's most beloved romantic comedies. A whirlwind New York love story, Serendipity stars Kate Beckinsale and John Cusack as two young city dwellers who meet and enjoy a magical night — only to decide to let fate control whether they end up together. As the years pass and their life paths diverge, it seems destiny has other plans for the would-be lovers, but New York City and a series of fortunate events may end up reuniting the pair after all. A missed connections comedy featuring an excellent supporting cast and a screenplay that is more than willing to lean into all of the best tropes of the genre, Serendipity is fun, funny, and guaranteed to make you yearn for a holiday season spent in the Big Apple. —I.G. Where to watch Serendipity: Max EW grade: A– (read the review) Director: Peter Chelsom Cast: John Cusack, Kate Beckinsale, Molly Shannon, Jeremy Piven, Bridget Moynahan, Eugene Levy Jennifer Aniston passed on Serendipity because Friends felt like doing a rom-com every week 22 of 27 Sex and the City: The Movie (2008) (From left to right) Kristin Davis, Sarah Jessica Parker, Cynthia Nixon, and Kim Cattrall in 'Sex and the City: The Movie'. New Line Cinema After spending six seasons either loathing or swooning over Carrie Bradshaw's (Sarah Jessica Parker) will-they-won't-they relationship with Mr. Big (Chris Noth), loyal Sex and the City viewers were gifted a feature film four years post-series finale to meet their curiosity. In this cinematic continuation, the ever-pensive Big ruffles Carrie's feathers by jilting her at the altar, thus prompting the N.Y.C. writer to turn her pre-booked Mexico honeymoon into a healing journey by traveling with her three besties: Miranda (Cynthia Nixon), Samantha (Kim Cattrall), and Charlotte (Kristin Davis). One of the highest-grossing rom-coms of all time, Sex and the City: The Movie is escapist fiction at its zenith, preserving the irresistible charm of the original series while injecting more melodrama, more luxury, more character development (albeit controversial), bigger and better closets, and — you guessed it — more sex. —J.M. Where to watch Sex and the City: The Movie: Max EW grade: B+ (read the review) Director: Michael Patrick King Cast: Sarah Jessica Parker, Kim Cattrall, Kristin Davis, Cynthia Nixon, Jennifer Hudson, Candice Bergen, Chris Noth, David Eigenberg, Jason Lewis Sex and the City: An oral history 23 of 27 Shakespeare in Love (1998) Gwyneth Paltrow and Joseph Fiennes from 'Shakespeare in Love'. Everett Collection Even Shakespeare suffered from writer's block, or at least that's the premise of the late '90s period romantic comedy, Shakespeare in Love. Joseph Fiennes stars as the Bard, a strapping poet and writer whose newest play Romeo and Ethel, the Pirate's Daughter is going nowhere fast — much to the dismay of Philip Henslowe (Geoffrey Rush) who owns the playhouse where the show is set to be performed. Inspiration strikes in the form of Lady Viola (Gwyneth Paltrow), a fan of Shakespeare's work and an aspiring actor who auditions for a role in his new work and ends up becoming his muse. Riddled with the love triangles, tragic miscommunications, and comic asides that have distinguished the playwright's work for centuries, Shakespeare in Love is, as EW's critic writes, "really about two great loves at once — the love of life and of art — and the way that Shakespeare, like no writer before him, transformed the one into the other." —I.G. Where to watch Shakespeare in Love: Max EW grade: A (read the review) Director: John Madden Cast: Joseph Fiennes, Gwyneth Paltrow, Geoffrey Rush, Colin Firth, Ben Affleck, Judi Dench, Simon Callow, Jim Carter, Martin Clunes, Antony Sher, Imelda Staunton, Tom Wilkinson, Mark Williams Julia Roberts quit Shakespeare in Love after disastrous chemistry reads, says producer 24 of 27 Singin' in the Rain (1952) Debbie Reynolds and Gene Kelly from 'Singin' in the Rain'. Everett Collection Widely considered one of the best musicals ever captured on film, Singin' in the Rain has everything from music and dance to comedy and romance. Released 29 years after the entertainment industry premiered its first movie featuring sound-on-film, the story stars Gene Kelly as a celebrated silent film actor struggling to make the jump to the "talkies," and Debbie Reynolds as an up-and-coming actress trying to break into the business. The majority of the film's comedy and over-the-top dance numbers are provided by the charismatic Donald O'Connor, and Jean Hagen makes a delightful (and Oscar-nominated) turn as Lina, a silent movie star with a face for film and a Brooklyn accent strong enough to stop traffic. A beloved treasure and shining representative from Hollywood's Golden Era, Singin' in the Rain continues to endure and inspire. —I.G. Where to watch Singin' in the Rain: Max EW grade: A+ (read the review) Director: Stanley Donen, Gene Kelly Cast: Gene Kelly, Debbie Reynolds, Donald O'Connor, Jean Hagen Every Singin' in the Rain reference in Babylon 25 of 27 Tiny Furniture (2010) Lena Dunham and Alex Karpovsky in 'Tiny Furniture'. IFC Lena Dunham made a name for herself as a filmmaker in 2010 with her debut indie, Tiny Furniture. Written, directed by, and starring Dunham — as well as her mother and younger sibling, Cyrus Grace Dunham — this rom-com is one of the first to investigate millennial post-grad life from the perspective of a real millennial. A definite forerunner to Girls, the film covers similar thematic territory and includes a few familiar faces. Dunham demonstrates an early understanding of her point of view, and whether you enjoy her particular brand of self-aware entitlement or not, the film stands up to critical analysis. EW’s critic writes, “ It’s a tiny tale of inertia, and it’s also the grand triumph of a young artist with a mature trust in her own unique voice.” —I.G. Where to watch Tiny Furniture: Max EW grade: A (read the review) Director: Lena Dunham Cast: Lena Dunham, Laurie Simmons, Cyrus Grace Dunham, David Call, Alex Karpovsky, Jemima Kirke, Amy Seimetz, Merritt Wever Lena Dunham apologizes to Allison Williams for making her sing Tracy Chapman's 'Fast Car' on Girls 26 of 27 A Star Is Born (2018) Lady Gaga and Bradley Cooper in 'A Star is Born'. Clay Enos/Warner Bros. It's a tale as old as time. While this is the fourth iteration of A Star Is Born — previous films were released in 1937, 1954, and 1976, respectively — Bradley Cooper proved why the story of doomed romance is, in fact, timeless. The director/co-writer/producer also stars as Jackson Maine, a washed-up country singer who falls in love with a budding singer-songwriter, Ally (Lady Gaga). Their romance is tested when Ally's meteoric rise to fame eclipses his, while he also struggles with alcohol dependency and substance abuse. With gripping performances, striking cinematography, and one hell of a soundtrack, this Star Is Born is one we love to revisit again and again, even knowing it'll break our hearts once more. —Kevin Jacobsen Where to watch A Star Is Born: Max EW grade: B+ (read the review) Director: Bradley Cooper Cast: Bradley Cooper, Lady Gaga, Andrew Dice Clay, Dave Chappelle, Sam Elliott Bradley Cooper wanted Howard Stern to shave his head and appear in A Star Is Born 27 of 27 Up in the Air (2009) George Clooney and Vera Farmiga in 'Up in the Air'. Dale Robinette/Paramount One of the only industries that thrived during the 2008 recession was the business of firing people. Such is the job of Ryan Bingham (George Clooney), a consultant who traverses the nation to deliver pink slips on behalf of corporations. Driven by an increasing airline status and distaste for interpersonal relationships, Ryan has distanced himself from his family and maintained only a FWB arrangement with a fellow business traveler (Vera Farmiga). But when he's confronted with Natalie (Anna Kendrick), a recent college grad who pitches ambitious ideas about the art of "downsizing," Ryan is prompted to reassess the life he leads. Helmed by Juno director Jason Reitman, Up in the Air is a charming, heart-wrenching, and thought-provoking exploration of a challenging period in U.S. history — all delivered in the guise of a clever, wry rom-com. —I.G. Where to watch Up in the Air: Max Director: Jason Reitman Cast: George Clooney, Vera Farmiga, Anna Kendrick, Jason Bateman, Danny McBride, Melanie Lynskey, Amy Morton, Sam Elliott, J. K. Simmons, Zach Galifianakis Movie critics: Our advice to friends when we're not on duty