Please give me your deepest cut indie film from the 90s/00s

As the title says, give me your deepest of indie film cuts! For reference, here are some movies i’ve seen recently that I am looking for more movies that are similar to:

  • Pieces of April
  • Thumbsucker
  • Me and You and Everyone We Know
  • Ghost World
  • Buffalo ‘66

Even if something comes to mind that isn’t necessarily a deep cut, please feel free to add it. I need to bolster my watch list🤘🏼🙂‍↕️