Country music from a fan's point of view since 2008
The Kingston Trio were pop stars for about a decade starting in 1957. While the number of hit singles they had was fairly small, they sold enormous numbers of albums and had a large and enthusiastic following, so much so that the group continues to perform to this day, although none of the original members are still in the group.
Who Were They?
Although often mistakenly classified as folk singers, and often excoriated by purists for not being sufficiently authentic, the Kingston Trio actually was a pop act that used folk instruments and dipped into the entire song-bag of popular music for their recordings. The group never regarded itself as a folk act.
The group was formed in 1956 by Dave Guard, Bob Shane and Nick Reynolds. Initially performing in northern California, the trio performed at the Italian Village Restaurant, where they developed a significant following for their unique blend of music and comedy. Their big break came in March when Phyllis Diller cancelled a week long engagement at the Purple Onion in June 1957 and the trio was asked to take the gig.
From here their fame spread quickly with appearances at the Village Vanguard in New York, Mr. Kelly’s in Chicago and Storyville in Boston. Signed to Capitol Records in 1958, their first album was a surprise hit in the form of “Tom Dooley” (an updated version of the old folk song “Tom Dula”), which sailed to #1 on Billboard’s pop charts on November 17, 1958.
While the Kingston Trio would never again have a hit of that magnitude, they would score ten top forty hits through 1963, with “The Reverend Mr. Black” reaching #8 in 1963.
The strength of the Kingston Trio was in album sales as they had five #1 albums, two #2 albums and three number three albums form 1958-1962.
Along the way the group received a Grammy for Best County & Western Song in 1959 for “Tom Dooley” and a Grammy in 1960 for Best Traditional Folk Album for AT LAST.
Dave Guard, who actually was a bit of a folk purist, left the group in late 1961, to be replaced by John Stewart. The group would continue until June 1967 when they disbanded. All told they charted twenty albums before the 1967 disbanding.
What Was Their Connection to County Music?
The Kingston Trio never actually landed an single or an album on the country charts. Their importance to country music is that they recorded many country songs. Billy Edd Wheeler, who wrote such county classics as “Jackson” and “Coward of The County” got his first real exposure through Kingston Trio recordings such as “The Reverend Mr. Black”. Other country songwriters had songs on various Kingston Trio, country songsmiths such as Bill Monroe, Danny Dill, and Hoyt Axton.
Country audiences liked the Kingston Trio and their songs would occasionally get played on country radio – I heard “Reverend Mr. Black” and “MTA” with some frequency over the years. Moreover, many of the Kingston Trio records had a strong bluegrass feel to them as several members of the band played the banjo (and played it well). This country/bluegrass feel of Kingston Trio records became more pronounced after John Stewart replaced Dave Guard.
My Kind of Country 
That they were accepted by country audiences to such an extent in the early 1960s is a touch surprising, even with the bluegrass influences, because one of their big hits was an arguably anti-war ballad, Pete Seeger’s “Where Have All The Flowers Gone?” (in 1962). Also their 1963 Hoyt Axton cover “Greenback Dollar” was one of the first songs (maybe even THE first) to use the word “damn”.
And as a sidenote, following the trio’s disbanding in 1967, John Stewart went on to have a fairly diverse solo career, with his 1969 Nashville recording CALIFORNIA BLOODLINES (an early example of Americana), and his 1979 pop smash “Gold”.