By Jason M. Rubin

A new collection of unreleased demos, live performances, and studio recordings puts Crenshaw’s enduring pop gifts in the spotlight ahead of his November 11 appearance at Boston’s City Winery.

As the story goes, Marshall Crenshaw was performing in the touring version of the musical Beatlemania when, one night in his hotel room during the show’s Boston run, he decided to leave the cast and make his own album. He wrote about half a dozen songs in that hotel room, including his breakout single, “Someday Someway.” Those songs formed the core of his eponymous 1982 debut album. The very same eyeglasses that made him a dead ringer for John Lennon reminded critics and listeners of Buddy Holly (one of Crenshaw’s heroes), and it seemed early on that his career would be as short as that of the lanky founding father of rock and roll. After his next album, 1983’s Field Day, and another hit single, “Whenever You’re On My Mind,” he seemed to have lost the Midas touch.

Crenshaw then became typecast as Holly: he and his band performed in the 1986 film Peggy Sue Got Married (based on one of Holly’s biggest hits), and he portrayed Buddy in the 1987 movie La Bamba (about Ritchie Valens, one of his two doomed travel companions). He also contributed to both soundtrack albums, which sold much better than his own records.

Though less commercially successful than his early work would have predicted, Crenshaw stayed active, making his own music (though he has gone as much as five, six, and even 16 years between studio album releases) and writing songs for others (often, again, with more acclaim than the ones he recorded under his own name). Though he has struggled with writer’s block at various times in his career, critics never left his side, and he has a cult following that no doubt will go crazy for a new 14-track compilation CD that Crenshaw compiled himself from his own archives.

The Bootleg Sounds of Marshall Crenshaw: 1984-87 contains previously unreleased demos, live performances from 1986 and 1987, and long-lost studio recordings from his own archives, and will hit the streets on October 23. Unsurprisingly, perhaps, the set includes Crenshaw’s cover of Buddy Holly’s “That’ll Be The Day,” featuring Garry Tallent and Max Weinberg from Bruce Springsteen’s E Street Band. It also features a collaboration with British singer/songwriter Kirsty MacColl.

Marshall Crenshaw today. Photo: courtesy of the artist

Judging by “(We’re Gonna) Shake Up Their Minds,” which has been released as a single, Crenshaw’s writing skills and pop sensibility were still intact during this period. And a beautiful ballad, “They Never Will Know,” is a moving pep talk (to himself, perhaps) in verse: “You shouldn’t doubt yourself/Don’t ever hide/If you live that way/You go dead inside.” It’s easy to blame radio programmers for his lack of continuing success — so I will. There was never anything sexy about Marshall Crenshaw (certainly not his name); he played the nerd, but his was a relatable nerd: he geeked out on music and knew from hard experience how to write and sing about unrequited love without self-pity.

Curiously, the set — which was originally issued on vinyl exclusively for Record Store Day on April 18 — is culled from a very short time period, one that begins after the successes of his first two albums. Of course, no one knew at the time that radio would soon abandon him, and so the release, which includes early demos that he recorded at home, provides an interesting glimpse into the writing process of a young singer/songwriter still finding his voice on his subsequent albums, Downtown (1985) and Mary Jean & 9 Others (1987).

Crenshaw and his band — featuring Derrick Anderson on bass and vocals, Mark Ortmann on drums, and the deservedly ubiquitous Fernando Perdomo on guitar and vocals — begin a 16-date tour on October 27 in Toronto. The tour continues through the Midwest, Northeast, and East Coast, reaching Boston’s City Winery on November 11. He’s still worth clapping for.

Jason M. Rubin has been a professional writer for 40 years. He has written for The Arts Fuse since 2012. His books include SHORTS: A Sizable Collection of Short Fiction (2025); Villainy Ever After (2022), a collection of classic fairy tales told from the villains’ point of view; and Ancient Tales Newly Told (2019), a pairing of two historical romances, one set in 17th-century England and the other in Biblical Jerusalem and Sheba. Jason also teaches journaling workshops. He holds a BA in Journalism from the University of Massachusetts Amherst. Learn more here.