The Highwaymen had a major impact on the folk scene of the early 1960s. Apart from a couple of major hit singles, and appearances on The Ed Sullivan Show, they contributed a couple of future standards to the folk repertory ("Big Rock Candy Mountain," "All My Trials"), played a key role in the unearthing of a major, overlooked Leadbelly song, which later became a major new addition to the repertories of both Creedence Clearwater Revival and the Beach Boys, and also made the first recordings, or the first American recordings, of seminally important songs by Buffy St. Marie and Ewan McColl, respectively.
      Their origins go back to the late 1950s, when, for a time, it seemed as though every college was spawning a folk group or two or three. California's Menlo College led the way as the birthplace of the Kingston Trio, and a year later Connecticut's Wesleyan University was where the Highwaymen were born.
      They signed with United Artists, then a new record label started up by the movie studio of the same name, in early 1959, and cut a self-titled debut album soon after under producer Don Costa. That LP, released in the late summer of 1960, barely sold at all, despite the presence of Dave Fisher's "Big Rock Candy Mountain." A similar fate befell the single pulled from the album, "Santiano" b/w "Michael, Row The Boat Ashore," and that seemed to be the end of the story. They might never have been heard from again--the folk boom had spawned dozens of groups eager for a try at recording --but for the efforts of an independent distributor from Connecticut named "Big Ed" Dinello, he began pushing the single's B-side, "Michael, Row The Boat Ashore," and persuaded other distributors to promote it, and various disc-jockeys to play it. The record slowly became popular across the northeast and broke out nationally in 1961, rising to the No. 1 spot that summer. The Highwayman album, forgotten in the UA catalog, suddenly began selling a year after its release, catching everyone off guard when it charted in October of 1961, peaking at No. 42.
      The Highwaymen were still undergraduates while all of this success was coming their way. A third album, Encore, followed, but its release seemed to presage a downturn in the group's fortunes. The accompanying single, "I'm On My Way" b/w "Whiskey In the Jar," failed to chart during early 1962. An extended period of line-up shifts began as the members all graduated that June--Steve Trott announced his exit from the line-up in favor of enrolling in law school and was replaced by ex-Cumberland Three and Belafonte Singers member Gil Robbins; and the group was reduced to a quartet when Bob Burnett began a required six months of active duty in the Army Reserve. A fourth album, March On, Brothers, was issued late in 1962 by the four-man group, but neither it nor a single of "I Know Where I'm Going" sold anywhere near the levels of the Highwaymen's early releases.
      After graduation, the Highwaymen became much closer to the core of the urban folk music revival. All of them began living in Greenwich Village in late 1962 and started an extended engagement at the Gaslight Cafe. They were competitive with most of their rivals, and if they weren't topping the charts, their records still sold respectably, including a live album, Hootenanny With The Highwaymen, featuring the revived five-man line-up (Bob Burnett having finished his military obligation), cut in front of an audience at in a recording studio and issued in June of 1963, and an October 1963 follow-up, One More Time, which included the first cover of "Universal Soldier" by Buffy St. Marie, whom they'd met at the Gaslight, and the Ewan McColl-Peggy Seeger-authored "The First Time Ever I Saw Your Face." Another live LP, Homecoming, cut at Wesleyan, followed in the early spring of 1964.
      The group could have continued indefinitely--between the members, especially songwrit- ers Dave Fisher and Gil Robbins, and their manager, they'd shown a knack for composing or choosing good songs, and a respectable ear for songs that would become important, so that their clean-cut early '60s image (and their association with the early 60s hit "Michael, Row The Boat Ashore") was not a drag on their audience appeal as they moved into the more confrontational middle of the decade. The Highwaymen might've followed Peter, Paul & Mary and jumped across that chasm separating the folk-pop outfits from the harder, more topical political singers of the era, but for the fact that three of its members, Burnett, Daniels, and Butts, had never intended to dedicate their whole lives to music. Rather, the music was fun, and, as it turned out, a means to an end, in the form of relative financial security. They'd never planned on doing it for more than two years, and by 1964 were already passing that time limit.
      Each of the surviving members has had a thriving, full-time career, in or outside of music, but the group has continued perform a few weekends out of every year thru the 1990s. Indeed, the Highwaymen, with all of their other "firsts" in terms of cutting certain songs, may be the only folk group in the history of the United States to boast a sitting Federal Appeals Court judge, in the person of Steve Trott, in their line-up.
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