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Get nostalgic with these 12 ’90s romcoms streaming on Netflix

collage of 90s romcom people 3

Throw on some Airwalks and Jncos and revisit some of these romantic comedies from the era of flannel.

In light of the recent announcement that a remake of She’s All That is in the works via Miramax and the Weinsteins, we’ve been thinking a little about ’90s romcoms lately. OK, we’ve been thinking about them a lot—enough that we’ve turned to Netflix to see which romcoms from Generation X we can currently stream while we’re pretending to be doing work. As it turns out, there’s quite a few.

1) She’s All That (1999)

Ah, the film that prompted this roundup in the first place. According to Wikipedia, it’s a remake of George Bernard Shaw’s Pygmalion, which means that Pygmalion must be about a popular boy making a bet with another popular boy that he can make a girl that’s already absurdly attractive look absurdly attractive in a different way by the time that prom comes around. I’ve never seen the play, but that’s the gist of the film, anyway.

Its 1999 release made She’s All That the perfect bridge into the new millennium—a bridge that left Matthew Lilliard (sadly, as his his d-bag character steals every scene he’s in) and Freddie Prinze Jr. in the ’90s, and carried Anna Paquin and Paul Walker into the 2000s. But Rachel Leigh Cook’s “pre-makeover” appearance is now the “hipster” look in 2015, so the remake will inevitably end with the lead actress looking like Cook does in the beginning of the original. Ah yes, the circle of life.

2) Beautiful Girls (1996)

The title’s a bit misleading—it’s more about a group of late-20s male friends who are mystified by beautiful girls than it is about the beautiful girls themselves. Set in Knights Ridge, Mass., it’s plotless in the way of films like American Graffiti, Dazed and Confused, and Kicking and Screaming (the one Noah Baumbach directed—not the Will Ferrell soccer movie): It involves a 10-year high school reunion loosely wrangling a group of friends and analyzing the various ways their lives are in turmoil—which seem aimless until their last moments, when they suddenly reveal what they’ve been getting at the whole time.

This movie is guaranteed to make you fall in love with Sweet Caroline, and it features Natalie Portman from when she was always typecast the young girl with the old soul (cf. Ellen Page in the 2000s). It also features an excellent feminist smackdown from Rosie O’Donnell, who offers up a much-appreciated defensive rant on female pubic hair.

3) Four Weddings and a Funeral (1994)

This was the film that transitioned Richard Curtis from “the writer behind Blackadder” to “the writer behind every British romantic comedy that’s ever made your father cry.” That’s not a slight against Curtis; making my father cry takes a lot of talent, and I think Love Actually and About Time are legitimately great films. He also wrote War Horse, which, while technically not a British film, made your father cry nonetheless.

Honestly, the gist of the film is all in the title: Hugh Grant goes to some weddings, which he’s always late to, with the exception of the one that’s (spoiler alert) his own, and he also attends a funeral. He keeps running into old girlfriends at these weddings, and one woman (Andie MacDowell) who he falls in love with, and he does all this with a face that’s so handsome that it’s actually upsetting.

With It’s a Wonderful Life, they say “every time a bell rings, an angel gets its wings.” In Four Weddings and a Funeral, I say “every time Hugh Grant smiles, you remember that you hate your own ugly face.” Even with his handsomeness, though, nothing can save him from the fact that British weddings appear to be the biggest hassles known to humanity.

4) A Life Less Ordinary (1997)

Even when you account for the fact that this film is about kidnapping a man’s daughter for ransom money, and that it includes a bank robbery followed by a clandestine bullet removal by a veterinarian, this still feels like a quaint film for director Danny Boyle to follow Trainspotting with. Even with all that mayhem, it’s still a romantic comedy at heart (and in advertisement).

Like most Boyle films, this one takes place in a heightened reality, in which angels working as matchmakers disguise themselves as assassins and small-town banks can be robbed with relative ease (well, you’ll get yourself shot in the leg, but it’s not like any cops will look for you once you leave the parking lot).

There are a few appearances of Boyle’s trademark hyper-stylized visuals along the way as Ewan McGregor and Cameron Diaz stubbornly fall for each other, but things are mostly photographed in ways that are serviceable but not enthralling, which is presumably what prompted a very bored Boyle to make the most insane end-credits sequence ever, in which each character’s post-film fate is summed up with a fantastic claymation cartoon for no particular reason.

5) Clueless (1995)

This movie’s based on Jane Austin’s Emma, but it really feels more like the ’90s answer to Fast Times at Ridgemont High, and for good reason—both were directed by Amy Heckerling, and directing the defining high school films of two separate generations is a pretty cool thing to have under your belt.

Of all the films in this roundup, this one might be the most quintessentially 90’s. The soundtrack includes No Doubt and Radiohead’s “Fake Plastic Trees,” Mark Wahlberg is referred to as “Marky Mark,” and Paul Rudd mentions a Cranberries CD. There are plot points, but it’s not really accurate to say that Clueless has a plot—like the movies mentioned in the Beautiful Girls entry, this is more of a snapshot of a time and place than a singular, coherent story. But it’s a fantastically composed snapshot, and there’s a reason it was the clear winner of our unofficial staff poll of the best ’90s teen movies.

Wedgies

6) I.Q. (1994)

I give this movie a 10/10 based solely on the fact that it has a scene with Meg Ryan and Stephen Fry within the first three minutes of it. The rest of the movie could be Battlefield Earth, and that score would not change. Plus: Not only is Stephen Fry in the first scene, but he’s also a prominent character throughout the film, and watching him play both Meg Ryan’s ill-fitted fiancé and also the exact opposite sort of atheist that he is in real life is just a whole lot of fun.

Speaking of fun: Walter Matthau plays Einstein (it’s a period piece), and he’s absolutely perfect as the imagination-loving genius. It’s his love for imagination that makes him take a liking to a blue-collar car mechanic, played by Tim Robbins, who happens to be in love with Meg Ryan, who also happens to be Einstein’s niece. As is so often the case, the film largely consists of Einstein and his tight circle of intellectual friends giving Robbins’s mechanic character a makeover into being a leading mind in astrophysics, and culling Fry’s stuffy intellectual fiancé character away from the herd.

The overall tone is like if The Big Bang Theory were a period piece, shot really well, and didn’t make you feel guilty for watching it if you’re actually smart.

7) Sabrina (1995)

If you’re going to justify remaking a classic film from 1954 that was directed by Billy Wilder and starred Humphrey Bogart, Audrey Hepburn, and William Holden, you’d have to get Harrison Ford and Greg Kinnear to act in it, and Sydney Pollack to direct it. Luckily, that’s exactly what they did when they remade it in ’95 (evidently, back in the ’90s, remakes of classic pictures weren’t put together by people heavily dosed on ketamine and laughing gas).

Guiding the performances required to pull the plot—in which a 20-year-old woman and a 45-year-old man fall for each other—off, let alone with chemistry so good the audience won’t even ponder the age gap, takes a whole lot of talent, and it may have come off extremely weird in a lesser director’s hands. It’s not a classic film, but it’s a sweet one, and certainly worth watching for the performances alone.

As far as being a ’90s film goes, the only real giveaway is that Paul Giamatti gets 17th billing in the end credits. You wouldn’t see that happen after the ’90s ended.

8) While You Were Sleeping (1995)

At first blush, this movie is about love at first sight and stalking people, but it turns out that its message is more about love coming from unexpected places (and still stalking people, a little). It’s your typical ’90s romcom, with sweeping orchestral music and moments that, like most horror films, often have you screaming at the characters onscreen to just do something.

Honestly: This entire film’s plot could have been avoided if Sandra Bullock’s character told the Coma Man’s family, from the start, that she did save Coma Man, but didn’t actually know him. To her credit, she actually does try to say that, but, after being interrupted a couple times, she decides to just give up and pretend to be the guy’s fiancé and hang around his family’s Christmas parties and stuff.

I initially thought the plot was overly convoluted and stupid, but thinking about it more made me realize that it actually works on an allegorical level (if you consider that the story is all about genuine, unexpected connections being more important than love-at-first-sight fantasies). Plus, every character in Coma Man’s typical Wacky New York Family is funny, so the story can afford to slink a little bit, anyway—for the first two acts, that is. The last act’s general dumbness is not something that I’m smart enough to B.S. a justification for; it just drags on, and it’s stupid. Unluckily for you, your brain is just as stupid as While You Were Sleeping’s third act is, and even though you’ll know exactly what’s coming for a full half hour before it happens, you’ll still cry when it does.

9) Sliding Doors (1998)

I’d always thought the conceit of Sliding Doors sounded like an excellent concept for a short film, or maybe a late night, half-drunk conversation at IHOP, but I never watched it because I could never imagine how they’d manage to squeeze a feature out of it. Well, I was stupid: It actually turns out to work very well as a feature. It’s structured in a quantum style, covering the same time period but cutting between the two potential universes that were created when a pair of train doors closed—one in which Gwyneth Paltrow ends up on the train and one in which she doesn’t.

Luckily, we can easily tell which universe we’re currently in by Paltrow’s various bandages and hairstyles (things would have gotten awfully confusing without those surface level details in there). Writer Peter Howitt is only credited as a writer on one other film, which is a shame, because Sliding Doors is written really well. The characters always feel human, including the Bad Guy, who is an asshole but always stays on the jackass side of being cheaply evil. The ending, though… well, feel free to email me to discuss how stupid it is and how it is on so many levels. It’s rare to see so much good will earned by a film go down the toilet in a matter of six minutes.

10) Groundhog Day (1993)

If there’s an upside to Groundhog Day ruining director/longtime friend and collaborator Harold Ramis and Bill Murray’s friendship for 21 years, it’s the fact that the film responsible for that fallout turned out to be an immortal classic.

Like Phil’s ever-repeating day, Groundhog Day is endlessly rewatchable, and some of its quality may have actually come from Ramis and Murray’s on-set feud: Murray evidently wanted a far darker film and was so upset with the slapstick nature of the montage in which he kills himself over and over again that he deliberately acted, like any actor only showing up due to contractual obligations, as bored and disengaged as possible. The resulting performance of Murray’s disdain ended up perfectly reflecting Phil’s emotional state. If Murray had been in complete agreement with the film’s tone, his performance may have been less outstanding.

We’re lucky that the only big Groundhog Day movie is a good one—it’ll likely hold its crown of The G-Day movie for decades, and it deserves that crown. Even if, for whatever reason, Hollywood decides Groundhog Day movies are the Next Big Thing and releases a dozen of them, I’d find it hard to believe that any would be close to the quality of this one.

11) Chasing Amy (1997)

I was a massive Kevin Smith fan back in my high school days (’00-’04), and I can honestly say that I loved all of his films equally (although, technically, my favorite would change week to week). The only one I didn’t watch with an unhealthy frequency was Chasing Amy. Maybe it was too much rom and not enough com for me back then, but looking back on it now, it’s clear that it’s his best film. If I’d watched it more than Mallrats, I might be less of an idiot with girls today (I still thought a heartfelt speech could get you a girlfriend until approximately 2013, after it failed to work for the hundredth time).

It’s without a doubt Smith’s most honest work. Holden and Alyssa’s relationship is filled with so many pathetic actions and insecurity that it must have come from a painfully honest place in Smith’s heart. After Amy, Smith dipped into the surreal with Dogma, and then went full-blown screwball with Jay and Silent Bob Strike Back. When he returned to a more personal place with Jersey Girl, he was brutally gutted by critics and fans alike, and he’s never made anything serious again.

12) Sleepless in Seattle (1993)

I already wrote about Sleepless in Seattle in this roundup (No. 15), but this point bears repeating: When it comes to collaborations between Nora Ephron, Tom Hanks, and Meg Ryan, I prefer You’ve Got Mail. Unfortunately, that’s still not streaming on Netflix (and joy to the day when I can finally pour my soul out by writing about that one and hugely embarrass myself).

Sleepless is a good movie—perhaps even a classic—it just doesn’t connect with me like it does with a lot of other people. But, it does connect very much with a lot of other people, so definitely give it a go if you haven’t already seen it. 

Screengrabs via Netflix | Remix by Joey Keeton

Joey Keeton

Joey Keeton

Joey Keeton is an entertainment writer who reviewed streaming movies, comedies, and TV series for the Daily Dot. He's also written about podcasts, bizarre web culture, and politics.