2. Fight Club     View this image › 20th Century Fox When I saw it then: Were you allowed to be a teenager in the 2000s and not be completely in love with this movie? It’s soooo angsty. If I saw it for the first time now: Brad Pitt, Edward Norton & Co. are a bunch of whiney white boys upset that the world hasn’t given them every single thing they deserve. Men being Men doing Man Things (fighting!). Is there a woman in this movie? Oh yeah, Helena Bonham Carter, who’s basically a dark muse/sex object. Nice.

    If my husband’s best friend ever did this to me I’d be like bye. (Also, who was the costume designer for this mess??? Keira’s wedding look was r o u g h.)

4. The Breakfast Club     View this image › Universal Pictures When I saw it then: I mean, John Hughes, the Brat Pack, high school, 1985? Nothing not to love. If I saw it for the first time now: Yes, it’s a classic, and yes, it perfectly hits on all the terrible shit we all felt in high school, but for the love of God, WHY does Ally Sheedy need a makeover at the end to prove how conventionally pretty she can be? Oh, that’s right, so she can safely become Emilio Estevez’s romantic interest. And Molly Ringwald has to become Judd Nelson’s, of course, because his Yes, it’s a classic, and yes, it perfectly hits on all the terrible shit we all felt in high school, but for the love of God, WHY does Ally Sheedy need a makeover at the end to prove how conventionally pretty she can be? Oh, that’s right, so she can safely become Emilio Estevez’s romantic interest. And Molly Ringwald has to become Judd Nelson’s, of course, because his fist pump moment wouldn’t be believable unless he Got The Girl!

6. Armageddon     View this image › Buena Vista Pictures When I saw it then: I loved this movie. I. Loved. It. I don’t really know why. It was in space? And the whole planet was in mortal peril? I probably liked it because lots of stuff blew up. If I saw it for the first time now: Liv Tyler’s character — Bruce Willis’ daughter and Ben Affleck’s girlfriend — is literally a prop they pass between each other. While all the men are in space, saving the world, Liv Tyler is hovering around NASA, biting her nails nervously and crying a lot.

Buena Vista Pictures Buena Vista Pictures     Why couldn’t Liv Tyler be an astronaut, too?? YOU DESERVED BETTER, LIV TYLER.

7. Elizabethtown     View this image › Paramount Pictures When I saw it then: It was soooooo cute of Kirsten Dunst to make Orlando Bloom a mega scrapbook/playlist/map/thing for his big car trip to get over the loss of his dad. If I saw it for the first time now: Ah, yes, the Ah, yes, the original MPDG . No actual living woman would make such a huge, intimate project for a guy she still doesn’t know that well, just so that he can learn to live a more fun, carefree life. Seriously, nobody. Sorry straight dudes.

8. Pretty In Pink     View this image › Paramount Pictures When I saw it then: Another John Hughes classic. I identified hardcore with Molly Ringwald’s character as the ~edgy outcast~ and of course loved Jon Cryer as Duckie, especially for the Another John Hughes classic. I identified hardcore with Molly Ringwald’s character as the ~edgy outcast~ and of course loved Jon Cryer as Duckie, especially for the Try A Little Tenderness scene If I saw it for the first time now: The film’s narrative leads you to sympathize with Duckie — almost to the extent that you want him to “win” Molly Ringwald in the end — when it’s actually extremely uncool of him to bemoan being friend-zoned the entire movie. Just let Molly do her thing, man, she doesn’t owe you anything! And maybe you could just appreciate her friendship without having to get in her pants?

9. Big Fish     View this image › Columbia Pictures When I saw it then: This is a gorgeous movie about storytelling and the meaning of truth and a life well lived. The ending hits that sweet spot of sad and uplifting. If I saw it for the first time now: Ewan McGregor pursuing the woman who will eventually be his wife — whom he sees across the room ONE time and then decides he HAS to have her — is creepy af. He works for months just to learn little details about her, which he later uses to get her to marry him, even though they are COMPLETE STRANGERS. (Another thing — the talents of Jessica Lange and Marion Cotillard are wasted on boooooring wife roles.)

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