best romantic comedies of all time

say anything… how is this not on the list? If that notion produces a little eye roll, get those peepers back down, and then on to the screen before you miss some laughs. The idea of a “crazy” girl coming in and turning a straight man’s existence topsy-turvy is repeated countless times in this genre, from Bringing Up Baby to The Girl Next Door. There was plenty to find in the John Hughes, teen-driven era (Say Anything…, Pretty in Pink), and the bubbly ’90s decade that followed (Groundhog Day, Four Weddings and a Funeral, While You Were Sleeping). How can we not, with this ensemble cast of British romance all-stars (Hugh Grant, Emma Thompson, Liam Neeson, Colin Firth, and Keira Knightley, among others)? Hunt plays a waitress with a sick child for whom Nicholson—a mean, racist, homophobic, obsessive-compulsive writer and her regular customer in the restaurant where she waits tables—has some affection. So where better to start than Queens, New York? But mostly Hugh Grant’s. Dickinson and Hawkeye Star Hailee Steinfeld Relishes Playing Strong-Willed Characters Who ‘Use Their Voice’, 100 Best Movies on HBO Max (January 2021). Like many of the films on this list, Lost in Translation takes place in a bourgeois universe, where the greatest thing at risk is someone’s heart or future emotional happiness, but few films have so effectively crystalized the alienation of both travel and marriage as well as the difficulties of postcollegiate, and then midlife, malaise. Cheeky, subversive, and sexy as hell, this movie turned the tables on so many male-dominated rom-coms (courtesy of one very hot and heavy matchup between Bassett and Diggs, playing some 20 years her junior)—and passes the Bechdel test with flying colors. it had a 100% on the tomatometer up until about 2 years ago when a couple “new” critics ruined the perfect score. The story of a sellout leading man (Gene Kelly) who falls for the chorus girl (Debbie Reynolds) who might just change his life (and he hers), this 1950s romp through 1920s Hollywood really has it all: singing, dancing, and bedrock songs like “Make ’Em Laugh,” “Good Morning,” and of course, “Singin’ in the Rain.” It’s cute as hell and tap-happy to the extreme. Right (by having our hero, a struggling comedian—played by the irrepressibly honest and infinitely endearing Jenny Slate—get drunk with Mr. We have the dazzling wit of the early studio system (His Girl Friday, Bringing Up Baby), the realistic cynicism of the ’70s (Annie Hall, The Goodbye Girl), and the sweeping romance in-between (The Apartment, Roman Holiday). Otherwise, you could be making a big mistake—big. © 2021 Condé Nast. Based on Truman Capote’s 1958 (harsher) novella of the same name, Breakfast at Tiffany’s—the story of a friendship struck between a rarely employed writer, Paul Varjak, and his neighbor, the naïvely beautiful Golightly, a freewheeling party girl whose lifestyle is paid for by the rich suitors who surround her—is a building block of our Hollywood romantic fantasies. Melanie Griffith plays Tess McGill, a wily business school graduate working as a secretary at an investment bank with such memorable one-liners as “I have a head for business and a bod for sin.” When her boss (Weaver) steals her idea for a merger and then ends up out of commission (temporarily bedridden after a ski accident), Tess rises to the occasion: scheming with the support of her friends and maybe-lover (Ford), conniving, flirting, and using some good old-fashioned elbow grease to outwit her superiors, beat the boys, and claim the position she’s rightfully earned. Sure, Renée Zellweger loves Tom Cruise from the beginning—it’s a movie, after all, and he is Tom Cruise—but what Jerry Maguire gets to is what happens after that first kiss, after the honeymoon period, when we have to learn about the other person as a person and not just see them and their adorable puppy (or in this case, an adorable son, played by Jonathan Lipnicki) as an escape or alternative from our own lives. ...to make your rom-com collection a little less straight and narrow: Directed by Jamie Babbit, this dark comedy centers around religious high-school cheerleader Megan (Natasha Lyonne) being sent away to “straight camp,” where the staff attempts to turn her and her fellow queer teens toward the Lord. In the mid-to-late 1970s, New York was a bit of a cesspool: Crime was out of control, repeated requests for federal aid were denied, and the city was on the edge of bankruptcy. The way he grins while he smolders. Bring in Nicholson’s neighbor, a gay artist (played by Greg Kinnear) who has to lean on Nicholson’s character for help (beginning with care for his adorable dog), add a road trip, and you’ve got yourself one of the most delightful, well-thought-out comedies of the ’90s. But underneath all the masturbating with pastry and accidentally ingested semen cocktails, there’s real sentiment to the adolescent boys trying to find their way with women and vice versa. Love Actually is, actually, a rather clichéd Christmas rom-com, but jeez, we love it anyway. They imported a Jane Austen storyline of a meddling would-be matchmaker (Emma) into a bright pink, plastic, kids-are-adults world of Beverly Hills privilege populated by overly dramatic in-talk (“Whatever!”; “As if!”), lunatic high fashion, and decidedly unrelatable problems. In 1998 this film competed with Saving Private Ryan, Elizabeth, and Life Is Beautiful for best picture and managed to come out with the Oscar. 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