The Highwaymen

Observers might readily overlook the Highwaymen as purveyors of a folk approach that critics and tastemakers had largely abandoned by later decades. Their signature vocal blends, drawn from traditional material and ballads, received scant critical attention after the peak years. Moreover, their beginnings at the end of the 1950s as five college students focused on entertainment rather than activism placed them squarely in the hootenanny circuit instead of protest gatherings or teach-ins. In the early-1960s divide between folk-pop ensembles and the sharper, socially engaged performers such as Bob Dylan, Phil Ochs, and Tom Rush, the Highwaymen lined up with the Kingston Trio, the Chad Mitchell Trio, the New Christy Minstrels, the Serendipity Singers, and the Brothers Four. Even so, they exerted genuine influence on the folk landscape of that period. Beyond a pair of substantial chart successes and Ed Sullivan Show slots, they added lasting standards such as “Big Rock Candy Mountain” and “All My Trials” to the common repertoire, helped rescue an important overlooked Leadbelly number later revived by Creedence Clearwater Revival and the Beach Boys, and produced the earliest or first domestic recordings of key works by Buffy Sainte-Marie and Ewan MacColl.

Their story traces to the late 1950s, an era when numerous campuses were forming folk aggregations. Menlo College in California had already yielded the Kingston Trio, and Wesleyan University in Connecticut became the cradle of the Highwaymen a year afterward. During autumn 1958, Dave Fisher, Steve Butts, Bobby Burnett, and Chan Daniels connected via a fraternity performance, with guitarist Steve Trott joining amid rehearsals. Initially called the Clansmen on account of their Scottish and Irish selections—an appellation whose racial and political overtones remained unknown to the members in the Northeast at that time—they built a following at Wesleyan events and resolved to pursue a professional path and secure a record deal. Auditions at various labels proved fruitless, though they encountered manager Ken Greengrass. After taping their full song list for a demo, they appended “Michael, Row the Boat Ashore” almost as an afterthought. Greengrass proposed renaming the group the Highwaymen, drawing from the Alfred Noyes poem that also inspired one of Phil Ochs’s early favorites. In early 1959 they signed with the fledgling United Artists label, tied to the film studio, and recorded their debut album under Don Costa.

Issued in late summer 1960, the self-titled LP moved few copies despite containing Fisher’s “Big Rock Candy Mountain.” The extracted single “Santiano” backed with “Michael, Row the Boat Ashore” fared similarly, prompting United Artists to drop the act. An independent Connecticut distributor, “Big Ed” Dinello, then championed the B-side, convincing fellow distributors and disc jockeys to support it. The track gained traction across the Northeast and reached the national summit in summer 1961. The previously dormant Highwaymen album suddenly gained momentum, entering the charts in October 1961 and climbing to number 42. As their final undergraduate year began, the quintet found themselves stars, prompting United Artists to schedule new sessions. Standing Room Only appeared promptly, accompanied by Sullivan appearances and a packed weekend touring slate.

Their follow-up single “The Gypsy Rover” succeeded on the strength of its B-side “Cotton Fields,” also listed as “Cottonfields” or “The Cotton Song,” which disc jockeys favored. That choice yielded a number 13 hit and carried wider consequence: the number was a Leadbelly composition the singer’s estate had neither identified nor copyrighted until then. It became one of the estate’s most valuable properties, reaching a new audience that included Alan Jardine and John Fogerty, who later recorded it with the Beach Boys and Creedence Clearwater Revival. While these events unfolded, the Highwaymen remained undergraduates. Encore followed as a third album, yet its release coincided with a commercial dip; the single “I’m on My Way” backed with “Whiskey in the Jar” failed to chart in early 1962. Lineup flux commenced after graduation that June: Steve Trott departed for law school and was succeeded by Gil Robbins, formerly of the Cumberland Three and the Belafonte Singers, while Bobby Burnett entered six months of Army Reserve duty, shrinking the group to a quartet.

The four-piece issued March On, Brothers late in 1962, but neither the album nor the single “I Know Where I’m Going” approached earlier sales. Post-graduation, the members relocated to Greenwich Village by late 1962 and began a residency at the Gaslight Cafe, aligning more closely with the urban folk revival. Records continued to sell adequately even without top-chart placement; a live set, Hootenanny with the Highwaymen, captured the restored quintet before a studio audience and appeared in June 1963. October brought One More Time, which featured the first recording of Buffy Sainte-Marie’s “Universal Soldier,” encountered at the Gaslight, alongside Ewan MacColl and Peggy Seeger’s “The First Time Ever I Saw Your Face.” Another live document, Homecoming, recorded at Wesleyan, surfaced in spring 1964.

Over the early 1960s the Highwaymen broadened their scope. From the comparatively untroubled late-1950s climate, their grasp of folk material deepened. By 1964 they were interpreting songs by the Almanac Singers and fresh compositions such as Tom Paxton’s “Rambling Boy.” The ensemble possessed the capacity for sustained activity: songwriters Fisher and Robbins, together with their manager, displayed skill at selecting durable material, allowing their collegiate image and association with “Michael, Row the Boat Ashore” to coexist with the more contentious currents of the mid-decade. Three members—Burnett, Daniels, and Butts—nonetheless viewed music as a finite interlude rather than a lifelong vocation, providing financial stability without demanding permanence. They had never envisioned more than two years, and 1964 already exceeded that horizon.

The final United Artists album, The Spirit and the Flesh, arrived in autumn 1964, after which the group disbanded. Fisher and Robbins persisted in music, while Burnett, Daniels, and Butts entered graduate studies. Because the split remained cordial, occasional reunions occurred. With Burnett, Daniels, and Butts accommodating academic schedules, the Highwaymen recorded The Highwaymen on a New Road and Stop, Look, and Listen for ABC-Paramount. Sporadic regroupings continued; Fisher, Trott, and Daniels participated in the 1974 ABC broadcast The Great Folk Festival. Chan Daniels died in 1975, yet surviving members staged anniversary concerts at Wesleyan in 1987. A brief, amicably resolved dispute with the country supergroup of Waylon Jennings, Willie Nelson, Johnny Cash, and Kris Kristofferson culminated in a joint performance by both Highwaymen lineups in October 1990.

In January 1991 the original members reconvened at the World Folk Music Association concert in Washington, D.C., and thereafter performed intermittently. Each survivor maintained a robust career inside or outside music, and the group sustained a handful of annual appearances for years. Notably, Steve Trott’s presence as a sitting Federal appeals court judge marked them as perhaps the sole folk ensemble boasting such a distinction. Their 2007 live album When the Village Was Green earned substantial praise, though the later resurgence suffered irreversible losses with the deaths of Dave Fisher in 2010 and Bobby Burnett in 2011.