I'm a Big Star fan, and I think the music is great -- but I think the poster (inadvertently) hits the nail on the head here. Despite a great deal of cooperation from the "supporting cast", there doesn't seem to be much light shed on Big Star or Alex Chilton.
The point of the documentary shouldn't be to tell us how brilliant they were. (And worse, it spends a LOT of time having aging rock critics tell us how brilliant they were). The music should speak for itself, and the filmmakers' point should be to tell us why, despite said brilliance, they never hit it big.
I can think of a few points, all of which the film hints at, but doesn't really get into.
1) college radio and indie rock hadn't quite developed yet to the point where a non-pop band could get support, gig, and sell modest amounts of records -- i don't know if that's true, but it's pretty clear that guys who came after them, like REM and the dBs managed to handle 10 years of low album sales and come out of it just fine, likewise guys that came before like Lou Reed, Iggy Pop and Leonard Cohen. Why wasn't Chilton part of that "weird rock genius" circle? Was it being in Memphis? Was it him? Did the music miss some criteria for old boomers (like the OP - d'oh!) while at the same time wowwing all Gen Xers?
2) Bell was too into drugs, Jesus, and/or men to get along with the industry types (not picking on gay, druggie, Christians -- just pointing out that the film tiptoes around ways in which he might have been tormented or been an outsider or not gotten along with Chilton, without ever really taking a stand). Plus, the film hints at him being the real genius (when they talk about his posthumous "album" release), but I feel like they don't talk much about how the albums were made, so it's not really clear.
3) Chilton was just too weird. He went from Top of the Pops to drawing the dole in record time after leaving the Box Tops -- who weren't just 1-hit wonders -- then did it again after Big Star, then spent 10 years in the punk scene trying to live down his "pretty" music. That's a pretty serious contrarian streak if you ask me. Plenty of ex stars go on to be great songwriters or producers -- why not him? I don't feel like you get much of a sense of what he was like as a person out of this. (And as a side note, it's odd to have a rock doc without at least 3 ex-wives to talk about what a great guy / tortured genius / absolute arse HE was). Maybe, just maybe, he was a PITA so all the big label guys stayed well clear...
4) He didn't want to be famous. Growing up in the 80s and 90s in the disco backlash and the punk era, I was so anti-pop that I wanted my heroes to remain forever unpopular -- was Chilton of that ilk? He certainly ended up there by the time he was in the Panther Burns. Maybe Chilton left something out of his songs just so as to be forever unpopular? I'm no rock critic, but I do think Big Star has a weird way of making amazing hooks into merely good singles (but then again into great albums)
I think Dig! (about the Brian Jonestown Massacre) and 20 Feet from Stardom both take the same question and give you a bit more insight. This leaves me with more questions than before!
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