A Definitive Ranking of my Favorite 80s and 90s Rom-Com/Cult Classics

drive me crazy

1.) Drive Me Crazy (1999)

I don’t know how much more praise I can give one movie. If you follow me on Twitter (@literallyrachel), you inevitably know how much I love this movie considering the many tweets I have about it. Many of these tweets pertain to the main character, the love of my life, Chase Hammond, played by the ever-gorgeous Adrian Grenier along side co-star Melissa Hart of Sabrina fame. This movie is a combination of my favorite things: nerdy/alternative guys receiving a hot makeover (Chase was always hot tho); the “girl next door” feel; and a beautiful combination of what makes 90s movies so great—trying on clothes montages and a pop punk girl band playing at a high school centennial. I love you, Chase Hammond.

16 candles2.) Sixteen Candles (1984)

Jake Ryan. Simple. Samantha Baker, I am so sorry everyone forgot your birthday but you end up with a guy that melts my heart every time he smiles. I’m not actually sure what makes me love this movie so much that it’s #2 but it probably has to deal with Jake Ryan, the little butt cheek that Mike is, the adorableness of Farmer Ted, Long Duk Dong, and a baby John Cusack.

pretty in pink3.) Pretty in Pink (1986)

Thought about lowering this one just because ANDIE SHOULD HAVE ENDED UP WITH DUCKIE. BLANE IS A STUPID RICHIE THAT WILL NEVER LOVE ANDIE LIKE DUCKIE WOULD OR DRESS AS FABULOUSLY. I strive to be as fashionable as the Duckman. I love this movie mainly because of Duckie and his lip-syncing but also because it’s a sweet story between Andie and her father and she drives the coolest car and has the coolest boss at TRAX. I wish everyday I could dress and act as dramatically as Duckie and Iona and get rid of all the Blanes in the world.

Clueless4.) Clueless (1995)

Before rewatching it for this blog post, I wasn’t planning on ranking it so highly but omg I love this movie. For starters, it’s inspired by one of my all-time favorite Jane Austen novels. Number two: Paul freaking Rudd. When Cher walks down the stairs to go on her “date” with Christian and Josh stares at her…like that’s how I want a guy to look at me. And I want that guy to be Paul Rudd. But besides that, this movie is literally hilarious. Here are some of my favorite quotes, though I think I could honestly just copy and paste the entire screenplay and it have the same affect:

“Do you know what time it is?” “A watch doesn’t really go with this outfit Daddy.”

            “You see how picky I am about my shoes and they only go on my feet!”

            “So, okay, I don’t want to be a traitor to my generation and all but I don’t get how guys dress today. I mean, come on, it looks like they just fell out of bed and put on some baggy pants and take their greasy hair—ew—and cover it up with a backwards cap and we’re supposed to swoon? I don’t think so!”

“What’s with you kid? You think the death of Sammy Davis left an opening in the Rat Pack?”

The_Breakfast_Club5.) The Breakfast Club (1985)

It’s a classic and it’s perfect.

220px-Shes_All_That6.) She’s All That (1999)

Very similar to Drive Me Crazy in that the nerd gets a makeover and the popular person that made them over falls for them. The best.

Ferris_Bueller's_Day_Off7.) Ferris Bueller’s Day Off (1986)

I love Ferris Bueller’s innovation. My senior year of high school I too missed a lot of school, more than Ferris himself actually, but because I actually got sick so I wasn’t able to steal my best friend’s Dad’s car and take it to downtown Chicago to go to the Hancock Observatory and to the Art Institute of Chicago. Instead, I ate five grapes in three days and passed out in the shower and broke the toilet seat off the toilet and hit my head on the bathroom cabinets.

say-anything_14226381448.) Say Anything (1989)

FORGOT HOW MUCH I LOVE JOHN CUSACK UNTIL I REWATCHED THIS MOVIE. I want to be in love with a Lloyd Dobler. Say Anything is by far the most romantic movie on this list. A must watch if only to fall in love with the gentleman that Lloyd is. Also I think Diane could be Can’t Buy Me Love’s Cindy’s twin sister. Anyone else see it?

cant buy me love.jpg9.) Can’t Buy Me Love (1987)

Similar to Drive Me Crazy and She’s All That. I think if I have a type of movie it’s this: pay/force/agree to date a person that will eventually fall in love with you only after a dramatic and public fight that takes place at a high school in suburbia. Maybe it’s because I think if I paid someone enough to date me they’d have to fall in love with me because I’m so perfect?? Also Patrick Dempsey.

And that’s it! How would you rank these movies? Which ones have you or have not seen? If you haven’t seen all of these we have a problem, come over immediately and we’ll have a movie marathon. Any movie you wish had been included? Leave me a comment and as always, thanks for reading!

P.S. If a guy who looks like Chase Hammond, dresses with as much sass as Duckie, smiles like Jake Ryan, has the manners of Lloyd Dobler, and is as socially aware as Josh is reading this, please dear God marry me. And because I’ve just described the world’s most perfect man, I call dibs on this person if he is real and the person reading this has met him.

2 thoughts on “A Definitive Ranking of my Favorite 80s and 90s Rom-Com/Cult Classics

  1. I haven’t seen ALL of the movies but I totally agree with the rankings of the ones I have. I may need to rewatch Drive Me Crazy though bc Clueless is honestly I think my fav movie of all time. ❤


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