Easy Rider, which I always thought was a Dad Movie (based solely upon my dad watching it a lot) until I watched it one day just because I love young Peter Fonda and Jack Nicholson and actually enjoyed it.
10 Things I Hate About You, for those days where you are missing Heath Ledger and/or the delia's catalogue.
It's the perfect time of year to indulge in some teen angst with a body count by watching Heathers.
Okay, I admit I haven't seen this one yet, but I really want to because I'm a sucker for all things Groupies. Mention Pamela des Barres, Pattie Boyd or Cynthia Plaster Caster and I'm hooked, and this documentary promises me those things.
LIFE DOESN'T HOLD TRYOUTS. If you don't like Center Stage, check your pulse, man. It's got everything you could want - 90's overalls, a Michael Jackson dance sequence, Peter Gallagher's eyebrows...
This film about the Beatle's recording of Let It Be has not been available publicly since the 80s, and circulates now only on bootleg and apparently, YouTube.
The best resource I've found for YouTube movies is MovieFork, but Buzzfeed looks like they've compiled a little Best Of using Reddit as a source. I really love that they included a link to You Got Served, which I maintain is one of the most underrated movies ever.
I just realized that over half of these are music-centric movies, so I am now taking recommendations from YOU on your favorites! I can't get enough, be it the good (Almost Famous) or the very, very bad (Center Stage 2...).