Bobb Trimble special is that although the neo-psychedelic singer/songwriter has generated a tremendous level of collector mania in the quarter century since his two albums were self-released in editions of 300 copies each -- near-mint copies of 1981's Iron Curtain Innocence have changed hands for over $1,000 -- his music is actually quite good, with intrinsic merits beyond the rarity of his albums or the back-story of his somewhat troubled artistic career. As a singer, Trimble has a high, tremulous voice that's garnered comparisons to T. Rex's Marc Bolan, Sparks' Russell Mael, and even Joni Mitchell. As a songwriter, his lo-fi psychedelia is tinged with an emotional intensity not often seen in the work of better-known '80s neo-psych contemporaries like R. Stevie Moore, Robyn Hitchcock, and the Bevis Frond. Trimble's two albums may allude to the late '60s in sound and songwriting, but he's actually closer in spirit to modern-day artists like Neutral Milk Hotel, Smog, and the "freak folk" revival spearheaded by Devendra Banhart and Joanna Newsom.
Trimble grew up listening to the usual classic rock staples, particularly the Beatles. ("Dear John, Paul, George and Ringo: If I'm a good boy and work real hard, may I please be the 5th Beatle some day?" read the liner notes of Iron Curtain Innocence.) Gravitating westward to the blue-collar city of Worcester, Trimble began performing on the local punk scene in his early twenties, while writing and recording the unquestionably non-punk songs that would be released in 1981 as Iron Curtain Innocence. Following that album, Trimble formed a garage rock backing band called the Kidds, who also performed on his far more experimental second album, 1982's Harvest of Dreams. The Kidds were not fancifully named: Trimble's collaborators averaged between 12 and 13 years old. Besides making club gigs difficult, the Kidds supposedly broke up due to the qualms of bandmembers' parents worried about their children spending so much time with the adult Trimble.
Trimble never released any further albums after the breakup of the Kidds, although he gigged around Worcester with a new, slightly older backing group called the Crippled Dog Band from 1983 to 1990 and continued to make sporadic unreleased recordings. In a November 2007 interview with the Boston Globe, Trimble claimed not to have written a single song since 1993. However, interest in Trimble's career continued to develop through the psychedelic underground, as tapes of the two albums circulated and the prices collectors paid for originals climbed. In 1995, the reissue label Parallel World released a CD called Jupiter Transmission that collected 13 songs from the two albums, further increasing the buzz. Meanwhile, Kris Thompson, a mainstay of the Massachusetts psych rock scene whose early-'80s band the Prefab Messiahs had played around the same Worcester punk scene as Trimble, became a vocal proponent of Trimble's music. His band Abunai!'s 2000 album Round-Wound features Trimble playing guitar on one track, and Thompson did the liner notes for an archival vinyl release called Life Beyond the Doghouse in 2002, featuring one side of previously unheard studio recordings made after Harvest of Dreams and one side of live tracks by the Crippled Dog Band. After the gray-market U.K. reissue label Radioactive Records released an unauthorized CD of Harvest of Dreams in 2005, Thompson urged Secretly Canadian Records (whose act the Impossible Shapes had been compared to Trimble in a review) to properly issue both albums, with full-color covers, extra tracks, and superior sound.