The cover songs were composed differently from the original versions by the performers; they changed the melody of the Madonna tracks by tweaking the lyrics and re-interpreting the actual meaning.

In February 2007, Los Angeles-based Manimal Vinyl record company announced its plan of releasing a compilation album containing cover versions of songs by American singer Madonna.

Manimal Vinyl label head Paul Beahan confirmed that 25% of the profit earned from the album sales would be donated to Madonna's Raising Malawi foundation.

"The Madonna tribute came to me in a dream last fall, and I immediately started making calls and emails to Winter Flowers, Chapin Sisters, and Banhart asking them to record a song for it," Beahan clarified to Spin magazine.

[9] The synthpop-influenced covers of "Into the Groove" and "Everybody" by Jeremy Jay and Ariel Pink, respectively, were given as examples by Deusner, emphasizing the post-punk era of the songs, but still being different enough from Madonna's versions.

[11] A guitar-influenced version was created by Golden Animals, who turned "Beautiful Stranger" into a swamp blues track by removing the chorus and making it reminiscent of songs by Creedence Clearwater Revival.

A freak folk recording of "Lucky Star" was composed by Alexandra Hope, while Lion of Panjshir included a multi-array of instruments in "Crazy for You" like sitar, tabla and acoustic guitar, with lead singer Ariana Delawari belting in breathy vocals.

[9] The Crosby, Stills, Nash & Young-influenced version of "Live to Tell" was created by the Winter Flowers, with "desert sunset atmosphere, noodly guitar fills, epic solos, and gorgeous harmonies sung by [lead singers] Astrid Quay and Gavin Toler".

[10] Chris Morgan from Treble noticed the lack of coherence in the album, but complimented the attention bestowed on giving prominence to the "hook and peppiness" of the songs.

However, he still found that "be it because their sound is not right for covering such an act or because they let their imagination run a little too wild for the sake of the art of reinterpretation, the creativity is vulnerable to quickly becoming a gimmick."