A quote from Trouser Press summed up Marshall Crenshaw's early career: "Although he was seen as a latter-day Buddy Holly at the outset, he soon proved too talented and original to be anyone but himself.

During and after high school he led the band Astigfa (an acronym for "a splendid time is guaranteed for all", a lyric from The Beatles' "Being For The Benefit of Mr. Kite").

[5] His second album, Field Day, was released in June 1983 with a bigger production courtesy of producer Steve Lillywhite that divided opinion at the time.

Despite Crenshaw's enthusiasm for the song, lead single "Whenever You're on My Mind" failed to reach the Hot 100, peaking third on the Bubbling Under charts.

Due to the commercial decline of Field Day, Crenshaw's relationship with Warner Bros. began to deteriorate and he sought to change his sound on his third album.

In 1986, Crenshaw and his band made a feature appearance playing in the high school reunion scenes in Francis Ford Coppola's film Peggy Sue Got Married,[7] and contributed "You Belong to Me" to the soundtrack album.

Also in 1986, Owen Paul's recording of "You're My Favorite Waste of Time" reached number three in the UK and was awarded a Silver Disc.

[9] In 1987, Crenshaw released his fourth album, Mary Jean & 9 Others, produced by Don Dixon and featuring Joe Jackson Band bassist Graham Maby on bass.

Crenshaw released two more studio albums during this period, Life's Too Short (1991) on MCA Records and the self-produced and largely self-performed Miracle of Science (1996) on the independent label Razor & Tie.

As the band's soundtrack contribution to the cult film Empire Records,[8] the song played over the closing credits and became a hit single in the US, reaching number 9.

[17] From 2011 until a hiatus in 2017, Crenshaw hosted a radio show called The Bottomless Pit on WFUV in New York, featuring his vast collection of recorded music.

[24] Many notable artists have recorded cover versions of Crenshaw's songs, including Lou Ann Barton, Ronnie Spector, Robert Gordon, Marti Jones, Bette Midler, and S Club.

[25] Scottish musician Owen Paul had an international hit with his version of Crenshaw's "You're My Favorite Waste of Time" in 1986, peaking at number 3 in the UK singles charts.

Gin Blossoms singer Robin Wilson cited Crenshaw as an inspiration, stating, "A few years back, I dug up one of Marshall's records and was listening to it.