As a cappella proliferated on college campuses across the United States in the 1990s, the genre found favor with audiences by reinterpreting familiar songs.

In 2004, Broadway producer and a cappella critic Elie Landau wrote about Deke Sharon's[A] long-standing concern with cover songs: "For nigh on forever, Deke has been urging collegiate (and professional) groups to consider a shift to performing some, if not entirely, original material lest modern "pop" a cappella go the way of the cover band—a novelty to listen to once in a while, but not anything anyone wants to buy or consider seriously and artistically.

"[3] Landau also praised lyrics written by Mike Solomon, saying they seemed "equally informed by the cadences and meter of Eminem as they do by the alliteration and internal rhyming of Sondheim.

"[7] Minkoff highlighted the album's storytelling, commenting, "The stories are so much more interesting than the typical baby-I-miss-you-cause-you're-gone crap clogging the airwaves.

"[7] Writing for The Recorded A Cappella Review Board, theater producer Elie Landau characterized the album's style as "Always wacky and zany... somewhere between the eccentric intellectualism of The Bobs and the somewhat more boisterous, more simplistic Da Vinci's Notebook.

"[3] Diamant wrote, "some seriously bad blend mars many of the tracks on Fleet Street, as though the group had spent too much rehearsal time writing songs and not enough singing.

"[10] In a 2018 interview, singer Connor Meany characterized the group: "We've definitely evolved over time, but I think we still have the same core values—writing our own music and being funny.

In 2007, three years after the album's release, music scholar Joshua Duchan wrote that, "at its core, a cappella is about originality achieved through some form of emulation."