Fellow anti-folk artists Jeffrey Lewis and Kimya Dawson first met in 2001, and created their first five songs that year.

Lewis' brother, Jack, Washington-based musician Karl Blau and drummer Anders Griffen soon joined them in the songwriting and recording process.

[3] Negative reviews included one written for Allmusic by K. Ross Hoffman, who awarded the album just two (out of five) stars and concluded that "...these Bundles may be best left unwrapped.

"[4] Among the most positive reviews was Robert Christgau's, in which he gave the album an A− and wrote that "...this is where Jeffrey Lewis replaces Adam Green in the Moldy Peaches...,"[6] while Jude Rogers gave the album a lukewarm review, writing that "these songs sound meatier than the members’ previous efforts" but also concluding that "it's a shame that this album’s playfulness very often comes across as pretentiousness.

"[11] The album was also praised by the Independent's Simmy Richman, who described its songs as "utterly charming and fall[ing on] just the right side of twee - think late-period Velvet Underground if Moe Tucker had had equal billing to Lou Reed.