My inspiration for this list was an imaginary (though certainly very real) film lover who's seen plenty of widely-acclaimed major productions, felt their interest piqued by under-the-radar, experimental and/or commentary-heavy works, and wants to delve deep into the world of indie filmmaking for the first time.
This list is curated to showcase a combination of 'essential' indie staples and more obscure fare; representation of the past 6 decades (with an emphasis on more recent works); a wide range of genres, styles, budgets, themes and topics; and a decidedly high level of control for the experimental, mind-bending, psychedelic, overly-symbolic elements that often confuse in more arduous, 'out-there' indie films.
While this list is intended to be well in-reach for the beginner indie fan, it's sprinkled with works that will playfully push that boundary - an enjoyable challenge that'll put enough titles under your belt to level-up as a film geek.
Enjoy! - M.C.