A 36-song double album, The Headphone Masterpiece features neo soul and lo-fi music, and distorted, overdubbed production.

After unsuccessfully shopping the album to record companies, Chesnutt distributed it himself on his website before releasing it again through his own label Ready, Set, Go!

[5] A 36-song double album, The Headphone Masterpiece has overdubbed, distorted production,[1] and incorporates pop rock, soul, R&B, and hip hop styles.

[7] Jared Levy from Tiny Mix Tapes called it a neo soul album,[8] while The Fader magazine's Knox Robinson categorized it as lo-fi music.

[1] Pitchfork journalist Rob Mitchum wrote that "Serve This Royalty" celebrates Chesnutt's "cultural sect", and "The Seed" mixes his "hypersexual egotism" with "a tone of evolutionary bravado.

"[16] Matt Diehl from Spin regarded the music as "indie soul that traverses the chasm between Shuggie Otis and Guided by Voices".

[17] Writing for Vibe, Dream Hampton said it is "everything that many roots and retro artists have reached for, pure and straightforward; yet it is thoroughly modern in its outlook, inventive and unsentimental, with both feet in the future.

Mojo found the record "at once engaging and aloof", with "its often hamfisted production and errant vocals adding to its ramshackle, rusticated charms".

[18] Mitchum from Pitchfork observed "a surplus of uniqueness overshadows a respectable aptitude" and remarked that its "self-indulgence, lack of focus, and unbridled sonic and lyrical crudity" makes the album "so frustrating, yet compelling.

"[9] Village Voice critic Robert Christgau cited "Family on Blast", "The World Is Coming to My Party", and "My Woman, My Guitars" as highlights and said the album is "just what alt-r&b needed—loads of ideas, considerable talent, and all the stern self-discipline of a trust fund baby".