Bobb Trimble released two LPs in the 80s, which became collectors' darlings because of their rarity and quality. The albums, Iron Curtain Innocence and Harvest of Dreams, have recently been reissued with slightly less tacky covers.
One can certainly find flaws in the records, but they're surprisingly good. And not in a forced, "I'm so clever to like Jandek" sort of way. The records' flaws aren't their obscurity, but their cheesiness. Bobb's psychedelic music is loaded with flange, and he sang in a high, womanly register about his sorrows.
You can hear his songs on his myspace page. For happy uptemponess, there's "Premonitions The Fantasy", and for the more representative, I'd suggest "Night at the Asylum", which dirges along until it breaks into a lovely release.