The group performs original songs and sketch comedy, and wears a uniform of black vests and red bow ties.

In its early years, the group arranged and performed many Stanford-related songs (which they often subverted for humorous effect), which earned them large audiences among Stanford students and alumni.

Alongside a turn to more popular music, the 1990s saw Fleet Street gain national prominence, sweeping the Contemporary A Cappella Recording Awards, appearing on national television (The Today Show) and radio programs (The Dr. Demento Show), at the Lincoln Center in New York City, and overseas (at the Edinburgh Fringe Festival).

They performed a parody of UC Berkeley's official fight song, with alternative lyrics lampooning the rival school's mascot ("The Dirty Golden Bear").

[1][8] The Stanford Daily called it "a performance that characterizes the group's combination of music and comedy" and reported by 1990 its use at official university events including freshman orientation, fundraisers, and Big Game.

In early 1992, Fleet Street released 50-Minute Fun Break, their fourth studio album and their second collaboration with audio engineer Bill Hare.

"[17][21] Over the summer break in 1992, Fleet Street performed in a weeklong appearance at the Edinburgh Fringe Festival, their first show outside North America.

The festival's program notes called Fleet Street "one of the U.S.'s premiere a cappella groups", and praised them for their theatrical style, musicianship, and "outlandish humour".

[25][26][27] Galindo later wrote that he found the recording "so spiritual and moving" that "the voices of the choir lift me to another state of mind, and it feels as if I'm floating.

The track "Greatest Hits of the 1590s" was described by a cappella critic Rebecca Christie as a "parody medley that [is] the best of its kind" with modern pop hooks "sung in madrigal fashion".

[42] As of 2020, Fleet Street is best known for their original, often humorous songs, such as "Prayer to the God of Partial Credit", "Everyone Pees in the Shower", and "Greatest Hits of the 1590s".

[39][46] Apart from music, Fleet Street is known for incorporating videos, sketch comedy, computer-animated films, and elaborate sets into their live performances.

[39] In 2011, The Daily reported on Fleet Street's May show, calling it, "filled with the silly, goofball antics the tuxedoed singers are known for.

"[49] Fleet Street is a student-led organization; the group's music director, business manager, and singers are always Stanford students.

[1][2][51] Fleet Street wears a uniform of black tuxedo vests and red bowties, a staple of the group since its founding.

That year, Fleet Street won the West Region semifinal and competed in the championships at Lincoln Center in New York City.

[94][95] In 2008, Fleet Street alumnus Matt Hempey led that group to win the Webby Award for Best Viral Video with their a cappella parody, "Here Comes Another Bubble".