The Bootheels were a premature supergroup. They were four high school age kids who were essentially unknown outside their neighborhood during their brief existence in the late 1980s, but a few years later, the former members would be working with the Wallflowers, Moby, Lana Del Rey, the Freewheelers, and Those Pretty Wrongs. Playing scrappy garage rock clearly informed by the Replacements, their music was fueled by adolescent angst and nervy energy, but they already knew how to write songs, and the talent that would lead the musicians to stardom is audible in their surviving recordings, if in rough form. The Bootheels didn't release any recordings during their months together, but a collection of their rehearsal tapes was released decades after the fact on the 2021 release 1988: The Original Demos.

Luther Russell was born and raised in Los Angeles, and started playing drums when he was five years old. By the time he was seven, he'd begun writing songs, and he was proficient on guitar and bass by the time he formed his first bands in his teens. Meanwhile, guitarist Tobi Miller (aka Tobias Miller) had been playing rock & roll since he was in seventh grade, and in 1988, his most recent group was in need of a bass player. Russell was buying bass strings at a music store when he met Miller; when Miller discovered Russell not only played bass but was a big fan of the Replacements, he asked him to join a band he was putting together with a friend who also played guitar. Russell was soon introduced to Jakob Dylan, a talented guitarist whose father had enjoyed a certain degree of success in the music business. With drummer Aaron A. Brooks rounding out the lineup, they adopted the name the Bootheels, and set up a rehearsal studio in the garage at Miller's mother's home. Russell had dropped out of school and gotten a GED, while Dylan attended a private school with a lax attitude about attendance, so the band kept up an unusually busy rehearsal schedule, and his bandmates soon discovered Russell had a keen talent for songwriting, as did Dylan. The band would practice during the week, and then invite neighborhood kids to watch them play on Fridays and Saturdays. They attracted a loyal following among fellow teenagers, though they had to deal with unenthusiastic homeowners and police who didn't care for the noise.

The Bootheels set up a makeshift four-track recording system in their rehearsal space, and cut demos of their original songs as they gained skill and confidence, though their only session in a proper recording studio was spoiled by shoddy equipment. However, the fact that three of the four Bootheels were under 18 made it difficult to get paying gigs, and beyond a pair of opening slots at Hollywood clubs, their performances were limited to parties and their public rehearsals. By the end of 1988, Dylan had decided to leave California to attend art school in New York City, and his departure put an end to the Bootheels. Russell and Miller formed a band called the 45s, but the project didn't last long, and when Dylan returned to California, he and Miller formed a band called the Apples, who initially featured Brooks on drums. The Apples eventually matured into the Wallflowers, who issued their debut album in 1992, and scored a multi-platinum hit with 1996's Bringing Down the Horse. Meanwhile, Russell formed a group called the Freewheelers, who released the first of three albums in 1991; he went on to a critically acclaimed solo career, and in 2016 debuted Those Pretty Wrongs, in which he collaborated with Big Star drummer Jody Stephens. Aaron A. Brooks went on to a successful career playing in the studio and on the road with Moby, Lana Del Rey, Duff McKagan, Janelle Monae, and Leisure Cruise. among others. In 2018, Russell released a career-spanning collection titled Selective Memories: An Anthology, which included two unreleased Bootheels demos, marking the first public release of their music. Omnivore Recordings offered listeners a more complete look at their repertoire with 2021's 1988: The Original Demos, featuring 13 tracks on LP and three more on CD and digital editions. ~ Mark Deming, Rovi