Cherry Peel

Prior to Cherry Peel, Kevin had made cassette four track recordings to share with friends and family. They had sent some of these to independent record labels in hopes of interest, and out of this, Bar/None Records ended up signing them.

Kevin was then given a budget of $3,000 to record an album. Bar/None partially gave the advance with the expectation that Jeff Mangum, the frontman of Neutral Milk Hotel who had just released the critical hit On Avery Island would be co-producing. Jeff told Kevin that he would allow them to use his name to more easily get the deal but had no real intention to do so as he was busy.

Julian Koster, also of Neutral Milk Hotel was instrumental however in helping Kevin throughout the recording process, also a home recording enthusiast, who Kevin befriended along with the other members of Neutral Milk Hotel and Olivia Tremor Control. These bands moved into a house together as they all began self-releasing material and playing on each others' albums and live sets. This solidified what became known as the Elephant 6 Collective.

Bar/None encouraged Kevin to record the album in a studio, but Kevin was used to intimate home recording and did not like the sound of '90s studio polish. They vyed for a contemporary 1960s folk-pop analog feel, akin to influences The Kinks Are the Village Green Preservation Society and early Paul McCartney. They acquired an eight track quarter-inch reel-to-reel TASCAM to record the songs at home as they were used to doing. They also purchased multiple contact PCM mics and a tape machine from RadioShack, often using the internal microphone to give vocals a signature more distorted sound.

The live lineup of the time consisted of Kevin Barnes on vocals and guitar, Derek Almstead on drums and The Late B.P. Helium on bass. Songs recorded with this lineup consisted of "I Can't Stop Your Memory", "Sleeping in the Beetle Bug", "Montreal", and "You've Got a Gift". When the album was overdubbed and remixed in 1999, "Don't Ask Me to Explain" was also re-recorded by this band, the original version being a solo four track recording. The rest of the songs were recorded entirely by Kevin.

The majority of the songs were written prior to the recording of the album, some of them being the songs presented to the label as four track recordings before Kevin was signed. Tracks that weren't re-recorded ended up being released on The Early Four Track Recordings compilation. "Everything Disappears When You Come Around" and "Baby" were written during the recording process of the album.

"When You're Loved Like You Are" was written about Kevin's uncle, who was dying at the time of cancer. He left Kevin $7,000 which they later used to buy another tape machine utilized on The Gay Parade and Coquelicot Asleep in the Poppies: A Variety of Whimsical Verse. Many of the songs, including "Don't Ask Me to Explain" and "Montreal", are about the pen pal girl from Montreal of which the band is named after, Julie. They eventually met after Kevin drove to Montreal to see her and it ended poorly. The experience devastated Kevin and became the lyrical inspiration behind the bulk of early of Montreal material.

During this period of writing Kevin also began exploring their sexuality and crushes through songwriting. "Tim I Wish You Were Born a Girl" was the first song written for the album, about best friend Tim Root. He became Kevin's muse, writing 'boy crush' songs and lyrics. "In Dreams I Dance With You", "I Was Watching Your Eyes" and "At Night Trees Aren't Sleeping" were written about another friend, Orenda. "You've Got a Gift" was written for Julian, being a thank you for helping them throughout the making of the album.

Due to the personal lyrics and complicated chord progressions, Kevin saw Cherry Peel as a more serious, introspective work than some critics and listeners did, denouncing the twee pop monkier it tends to be associated with. This, as well as the toll the failed Montreal relationship took, led to less personal, more abstract lyrical content and frantic musical styles from The Gay Parade until Satanic Panic in the Attic.[3]

• Derek Almstead - drums, vocals (tracks 3, 5 (1999 reissue), 7, 9 and 14)
• Bryan Poole - bass, vocals (tracks 3, 5 (1999 reissue), 7, 9 and 14)
• Kevin Barnes - guitar, vocals

drums, bass (tracks 1, 2, 4, 5 (original 1997 release), 6, 8, 10, 11, 12, 13)