The 16 Most Endearing Friendships Of The ’90s

These are the inspiring friendships that you desperately wanted in your own life during those lonely teenage years. Disclaimer: this is a totally subjective list. Maybe you were more inspired by Joey and Chandler, I don’t know.

1. Macaulay Culkin and Anna Chlumsky in “My Girl”

I wanted a boy best friend soooo bad after watching this movie. Too bad I didn’t learn how to talk to them until age 19.

2. Clarissa and Sam

Another fantasy of a boy best friend before sexual tension enters the picture.

3. Liv Tyler and Alicia Silverstone (in Aerosmith’s “Crazy” Video)

Despite how totally HOT this video is (re: Liv Tyler’s Silver Bra at 4:04), I sort of believe girls were more into this video than guys were. It’s a total fantasy of empowering, man-eating female friendship with a titillating hint of lesbianism.

4. Evan Dando and Juliana Hatfield

When I was 12 or so, I often thought and speculated about the lives of people I never met, which often included daydreaming about Evan Dando and Juliana Hatfield’s platonic love. They would take turns cooking each other breakfast, wear each other’s clothes and be perpetually sun-drenched, according to my teenage brain.

5. Little Pete and Artie

There were a few great friendships in The Adventures of Pete and Pete but there was something really simple and pure about Artie and Little Pete. When Artie realizes Little Pete doesn’t need him anymore, he leaves Wellsville for good. It’s a sad, poignant message about the pains of growing up.

6. Ben Stiller and Janeane Garofalo

They were the Fred Armisen and Carrie Brownstein of the ’90s.

7. These Three From “Freaks and Geeks”

Geeks are more endearing than Freaks in my book.

8. The Women of “Waiting To Exhale”

See, look how happy and cute they are despite the sh*tty men they date.That’s the sign of healthy, relatable, female friendships. P.S. the book is way better than the movie.

9. Missy Elliott and Aaliyah

Anytime Missy Elliott talks about Aaliyah after her death, it makes me want to CRY. Even this photo makes me want to cry.

10. Julie and Heather from Real World Season 1

This is the true story of a country bumpkin and a hardcore female rapper who end up as real friends. This season is on Hulu, by the way, and totally worth watching, if you want to immerse yourself in NYC during the early ’90s. Despite probably being the annoying hipsters of their time, the entire cast is crushworthy and awesome.

11. DJ Jazzy Jeff and The Fresh Prince

They were the Kanye and Jay-Z of their time. Lol, not really, but they dressed cute and made really good party rap.

12. Kim Gordon and Julie Cafritz of Free Kitten

They started a band and a clothing line together, which is exactly what you dreamt of doing with your BFF.

13. River Phoenix and Keanu Reeves

They met on the set of Parenthood in 1988. If not endearing, they were at least the cutest (in the literal sense) friends of the ’90s.

14. Jane and Daria

Jane and Daria taught me that it’s so much easier to bond over the things you hate than the things you love. Which is maybe why the friendship grew sour towards the end when a boy (that they both like) gets involved.

15. Rosie O’Donnell and Madonna

They became friends after playing best friends in A League of Their Own, the most tearjerking movie of the ’90s. You can picture them, all sassy-mouthed, just cracking each other up relentlessly.

16. Romy and Michelle

Just a little reminder that you can be a total fail at life and still have an awesome time with your BFF.

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