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Notes -
I’m continuing my tradition of using The Motte as a wildly inappropriate forum for suggestions about media.
I recently watched Clueless (1995) and 10 Things I Hate About You (1999) which are modernized teenage high school romantic comedy adaptations of Jane Austen’s Emma and Shakespeare’s Taming Of The Shrew. And I loved them. They are the perfect combination of lighthearted fun, warm and fuzzy positive vibes (particularly Clueless), (faux) nostalgia back to my teenage years, good performances (even iconic in the case of Alicia Silverstone’s Cher in Clueless) combined with great execution and obviously excellent source material.
What other similar light hearted teen rom com adjacent yet actually really good adaptations or even original movies from the late 80s to 2000s should I check out?
Taking your question in a totally different direction: the essential Romantic Comedies to watch to survey the genre
-- Love Affair (1939) or An Affair to Remember (1957). The classic, referenced in Sleepless in Seattle among other places, caught both on Turner Classic Movies when I watched a lot of it while studying for the LSAT. The climactic scenes are iconic for a reason. They're the same movie, watch the earlier one if you prefer a suave French protagonist, the latter if you prefer him American.
-- How to Marry a Millionaire Three young women cynically try to ensnare themselves a rich husband. Hijinks ensue. Marilyn Monroe at the point where you understand how she was able to single handedly launch Playboy and be the love of Joltin' Joe Dimaggio's life while also schtupping the President and the attorney general. If you like this, you can explore 50s comedies like Some Like it Hot.
-- Marriage, Italian Style Prime Sophia Loren and Marcelo Mastroianni. An irresponsible Italian playboy has a multi-decade romance with a beautiful prostitute. The acting is so good, the costumes so beautiful, and the setting so charming. If you like this Marcelo and Sophia made a whole pile of movies together.
-- Annie Hall Woody Allen's best, at his most neurotic. Don't watch this unless you can handle an intensely Jewish experience, but it's essential, however much it might be denied elsewhere. Woody Allen, like Phillip Roth, captures something of the darkest nature of male heterosexuality in a light and funny way. If you like this, Woody Allen made about a dozen rom-coms that all rank among the best ever.
-- What's Up Doc? Streisand presages the manic pixie dream girl, trying to snatch a straight laced man away from his boring and bitchy fiancee. A rollicking farce that ends with a madcap chase scene that I watched a million times on VHS with my sister.
-- When Harry Met Sally The GOAT. Simply the best Romantic Comedy of all time. Two acquaintances go from dislike, to friends, to companions, to lovers, over years and years. Ships passing in the night. The writing is good, the chemistry is perfect, and the interviews with elderly couples about how they met are sappy and sweet. If you like this, Meg Ryan did Sleepless in Seattle, You've Got Mail.
-- Sixteen Candles You need one of the John Hughes 80s classics, and I think Candles is better than Pretty in Pink and more of a pure romcom than The Breakfast Club, though I would also recommend TBC as a great film. Molly Ringwald turns 16, and through the homecoming dance gets the boy of her dreams. Watch it purely for Long Duc Dong, the exchange student often decried as a politically incorrect racist caricature, but who winds up with a STACKED white volleyball player by the end of the movie, so he does pretty well for himself I think.
-- Moonstruck Cher and Nicholas Cage star, and it's fascinating seeing Nick Cage in this offbeat part long before he'd be a bankable star for National Treasure type schlock. Intensely 80s, intensely NYC Italian. Cher is engaged to a schlubby man, but in order to complete the marriage must reconcile him to his brother, Nick Cage, who doesn't speak to his brother after losing his hand in an accident. Nick, of course, falls for Cher.
-- Mystic Pizza Three teenage girls in Mystic, Connecticut work at a pizza place, hang out, fall in love, get married, make mistakes. The paying the babysitter scene is the single greatest most gut wrenching scene in the entire RomCom genre. Julia Roberts at her best, better than Pretty Woman imo, though Mrs. FiveHour hates her teeth too much to pay attention to anything else. Slice of life New England stuff on top of the rest of it. Coming of age comedies don't come much better than this.
-- Tin Cup Kevin Costner did a whole pile of sports romcoms, I think this is the best, though Bull Durham gives me my personal text for the "IN THIS HOUSE WE BELIEVE..." sign in my front lawn. Costner is a burnout loser golf course pro, who is inspired by losing his lady love to a straitlaced PGA tour pro to go win the US Open with his caddy Cheech. Filled with bon mots, it's a great sports movie in addition to a great romcom, with the climactic scene capturing something essentially masculine in a way that can be tough to do in a romcom format.
-- Four Weddings and a Funeral The film that launched Hugh Grant's career. A group of friends see each other at weddings over the years, their lives evolve and change, romance blooms. NEVER EVER LET YOUR FIANCEE DO WEDDING SHOPPING WITHOUT YOU, HUGH GRANT WILL FIND HER AND STEAL HER FROM YOU. The writing in this is just so good, it's only flaw is that I find the female lead so unattractive as to be unfuckable, I'd probably sleep with 90s Hugh Grant first. The charmingly disheveled vibe that Hugh Grant carries through the film is what every man wishes he could be.
-- Can't Hardly Wait Not a pure romcom, but one of the essential 1990s teen movies, which even at the time tried to be aggressively of its time. The whole film takes place over the course of a single party summer after senior year of high school. The iconic image of the high school rager, the wigger poser, the high school rock band drama. Gorgeous storytelling in this film, captures a vibe of the 90s like nothing else.
-- High Fidelity (2000) The film that best captures the essence of hipsterism, the dominant cultural force for much of white America from 2005-2015 or so. A fascinatingly misanthropic male lead, and Jack Black in the role that launched his career. John Cusack is a sad sack record store owner, whose best friends are his employees Jack Black and the other guy I don't remember, who he doesn't really pay much so much as they sit around and bullshit about the Smiths and the Jesus and Mary Chain all day.
-- Crazy Stupid Love Probably the most recent great romcom I can think of. Ensemble cast with intersecting stories ending in a giant farce. Does a good job of deconstructing the early PUA genre. If you like this, Steve Carrell did a lot of this kind of stuff, 40 Year Old Virgin and Date Night are pretty good. Stories intersect from Carrell's wife cheating on him and Carrell trying to find his masculinity again, with Ryan Gosling stepping in as PUA mentor. Romcom self referential, and emblematic of the best the genre has had to offer after 2003 or so.
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