The Best Movies of my Angsty-Ridden Youth

When an alert popped up on my phone saying a third installment of Legally Blonde was in the works, I screeched like an over-eager baby seagull presented with a basket of french fries. I loved those damn movies and thinking about them reminded me of all those other movies I watched over and over and over again. They’re the movies from that very specific, nostalgia-spangled part of my young adulthood.  They’re the movies I watched repeatedly on VHS, the first ones I ever owned on DVD, the ones I watched over and over and over and the ones ones I still quote today.

Here’s a roll-up of a few of my favorites from the way-back-when:

Y’all, this is probably my favorite movie of all time. I vividly remember watching it for the first time at a middle school sleepover. We were probably a touch too young for it, but we were riveted. If you haven’t seen, I’m sorry. It’s the story of a bunch of music store employees banding together to save their favorite place. There’s drugs and sex and Rex Manning and friendship and a fake funeral and edibles and maybe one of the best soundtracks I’ve ever heard, one I still listen to today.

Favorite Quotes:

  • “Well Sinead O’Rebellion. Shock me, shock me, shock me with that deviant behavior.” -Gina
  • “Damn the man. Save the empire.” – Mark

I watched Boondock Saints for the first time in high school and have probably watched in 50 times since. I don’t know if it was the violence, the f-word-based monologue or the story of two Irish Catholic brothers cleansing Boston of evil, but this movie is one I never get tired of watching. Plus, Sean Patrick Flanery and Norman Reedus are delightful to look at.

Favorite Quotes:

  • “Well, that certainly illustrates the diversity of the word.” – Connor
  • “Why don’t you make like a tree, and get the fuck outta here?” – Doc

It’s possible I’m the only one that loved this movie or at least the only one who remembers it, but it’s one I definitely owned on VHS and watched almost every weekend. I was a big, big fan of Drew Barrymore and this was just one of the many movies of hers I watched on repeat in high school.

Favorite Quote:

  • “You can’t be the father and the brother! That’s the kind of thing that messes kids up!” – Sally

I know Pretty Woman is THE Julie Roberts movie of our youth, but this one was always my favorite. I don’t know if it’s because I was always the tom boy in a pack of boys, or what, but I found the whole premise of this thing absolutely delightful.

Favorite Quotes:

  • “It’s amazing the clarity that comes with psychotic jealousy.” – George
  • “You’re never gonna be Jell-O!” – Julianne

Along with Julia Roberts, I also count Reese Witherspoon as a national treasure and these movies spoke to the child in my heart who loved her Barbies to bits and pieces and wanted them to be badass boss bitches while wearing pink and carting around a teeny, tiny little dog.

Favorite Quotes:

  • Warner: “You got into Harvard Law?”
    Elle: “What? Like, it’s hard?”
  • “You look like the Fourth of July! Makes me want a hot dog real bad!” – Paulette
  • “I have always respected redheads as members of a hair color minority.” – Elle

What about you? What are your nostalgia-laden movie favorites? 


  • Rachael

    I’ve never seen Home Fries!!! Watching this weekend. Also god yes, I must have seen Boondocks Saints 4,294 billion times

  • Kristin

    I love Legally Blonde. They’re making a third??!! I’m so there for that. Guilty pleasure all the way. I have a lot of nostalgia for the cheesy rom-coms my friends and I used to watch in college. While You Were Sleeping, Someone Like You, and so forth. I think it was No Reservations with Catherine Zeta Jones that got me on a serious food kick, and showed me that someone with some serious control needs and potential anger issues could still make the family life work. Still love it!

  • Stephany

    Oh man, the only move I’ve seen off this list is Legally Blonde! I was a little too young when Empire Records came out, so I missed the boat on that one but I’d love to give it a try because I’ve heard amazing things.

    My nostalgic movies are Tommy Boy, Clueless, Liar Liar, and Never Been Kissed. 🙂 A strange mix of movies, haha.

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