[1] He graduated from The Hill School in Pottstown, Pennsylvania,[2] and then attended Williams College in Williamstown, Massachusetts, where he met future Fountains of Wayne bandmate Adam Schlesinger.

Though Collingwood and Schlesinger shared cowriter credit for all original Fountains of Wayne material, for most of their career together, they wrote their songs separately.

The band was nominated for a Grammy Award for their song "Stacy's Mom", in 2004, which charted at number 21 on the Billboard Hot 100.

Prior to his breakdown, he had been experiencing hallucinations for two days, and was sleep deprived and mentally unstable to the point that he did not believe he was actually in Japan.

The album also included contributions by: Davey Faragher (bass), Mitchell Froom (keyboard/producer), Mike Viola, Flora Reed, and Philip Price (all backing vocals), and was engineered and mixed by David Boucher.

Collingwood's major influences are The Beatles, The Zombies, The Hollies, Aztec Camera, Squeeze, and Blue Öyster Cult.