The album follows Red House Painters' 1992 debut
Down Colorful Hill, and the recording sessions spawned twenty-three songs culled from leader/producer
Mark Kozelek's back-catalog, fourteen of which comprised the
Rollercoaster album. Two songs featured on the record, “Funhouse” and “Strawberry Hill,” had previously been featured on a 90 minute demo tape recorded by the band between 1989 and 1992, alongside tracks from
Down Colorful Hill. “Dragonflies” and “Brown Eyes” had also previously been recorded as demos, and which were later released as part of the bands 1999
Retrospective compilation album. Eight songs left over from the recording sessions would make up the band's
second self-titled album. Kozelek's lyrics focus on themes of pain, desolation and loss, while musically the album runs from the folk-pop of "Grace Cathedral Park" to the shoegaze of "Mistress" to the stark "New Jersey" and onto the soundscapes of "Funhouse" and "Mother". Kozelek said of the recording sessions, "It was a nightmare, because the initial excitement of recording twenty-three songs became, 'one down, twenty-two to go' ... And I was nervous that people were now paying attention, but
Ivo [Watts-Russell, 4AD label owner] made helpful suggestions and never demanded anything. If we went over budget, we went over budget." Watts-Russell also suggested the album be a
double album, and compiled the track listing himself. Kozelek discussed his views of the album in the foreword of the 2002 and revised 2008 editions of his book of lyrics,
Nights of Passed Over: "... I know the
Rollercoaster album is many people's favorite. But for me, it is and will always be the most difficult to get through. I hadn't heard it in years, and though there are some beautiful things I had forgotten about -- a delicate piano in "Things Mean a Lot", the way the band brings life to "Brown Eyes" midway through, and the chorus of "Strawberry Hill", which was sung by a group of strangers we gathered from outside the
Divisadero Street studio where we were recording—what I remembered most, even when I look at the album's cover, is nine months of worry." The album cover is a sepia-toned picture of the now-demolished
Thunderbolt roller coaster at
Coney Island. ==Reception==