Top 10 Songs From The Kingston Trio

Photo: Photographer John A. Lee, CC BY-SA 3.0 <http://creativecommons.org/licenses/by-sa/3.0/>, via Wikimedia Commons

The folk revival between the late 1950s and the late 1960s owes its breath of life to The Kingston Trio and the young men who headed this band from Honolulu, Hawaii. Dave Guard, Bob Shane, and Nick Reynolds are the three original members who officially kick-started the recording career of The Kingston Trio in 1958, alongside their manager, Frank Werber. This group earned their first big break in June 1957 when comedienne Phyllis Diller was unable to appear at a popular club in California due to scheduling complications. When the audience first heard the Kingston Trio perform, their blend of pop-rock and folk music was met with rave reviews.

The popularity of the band soared, literally becoming the envy of many in the music industry, especially when Billboard Magazine awarded the Kingston Trio as Best New Singing Group in 1958.

Kingston Trio Influence

From 1957 until 1961, the Kingston Trio was at the top of the music industry chain. However, a rift began to develop in 1961, pitting Guard against Shane and Reynolds. Animosity over what roles each band member actually played reached a boiling point, with creative differences and royalty rights also at play. This led to Guard splitting from the group, leaving the door open for John Stewart to join and take his place.

By 1964, the popularity of the Kingston Trio began to wane. By 1967, the Kingston Trio everybody knew, loved, and imitated was no more. Bands like The Beatles and The Rolling Stones made everyone forget the Kingston Trio. Rock music had changed significantly when the Beatles arrived in 1963. The British Invasion, along with the sounds of groups like The Beach Boys, The Doors, and so many other ’60s rock acts, had turned the music world and pop culture upside down.

Top 10 Songs From The Kingston Trio

#10 – El Matador

We open our Kingston Trio songs list with the cool cut “El Matador.” The song was released on the third studio recording entitled Sold Out, which was issued in 1960. Despite the single only charting at number 40 on the US Billboard Hot 100, the album charted at number 1 and remained in the top 40 for 54 weeks. The bullfighting theme behind the song, with a rich mix of ukulele and vocals, is one of its special attributes.

#9 – Bad Man’s Blunder

The final top forty single on the US Billboard Hot 100 from the Kingston Trio, featuring Dave Guard, was “Bad Man’s Blunder,” which came from the 1960 String Along album. The radio-friendly version omitted the song’s final words, “Bang, you’re dead,” for commercial approval, as did the title, which became “Bad Man Blunder.” The tale of a lawbreaker who had to answer for his crime was spun melodically, with a hint of humor.

#8 – Desert Pete

Released from the album, Sunny Side!, “Desert Pete” was the final top-forty single for the group, Kingston Trio. It was chosen by the Western Writers of America as one of the top hundred songs of all time in 2014. Both the song and album were released in 1963, a time when Glen Campbell was part of the lineup and performed the banjo specifically for Desert Pete.

#7 – Where Have All the Flowers Gone?

On November 14, 1961, the Kingston Trio, now with John Stewart instead of Dave Guard, recorded the single “Where Have All the Flowers Gone?” which became a number 21 hit in 1962 on the US Billboard Hot 100. Drawing on the Cossack-inspired folk song, then modernizing it to suit the current political climate, the Kingston Trio delivered their version of a political rally song. It, along with the album College Concert, was the group’s third live release.

#6 – A Worried Man

In 1959, “A Worried Man” peaked at number twenty on the US Billboard Hot 100 chart. While the single itself was not a chart-topper, it contributed to the album Here We Go Again!, which reached number one on the US Billboard 200 for eight solid weeks and was certified platinum by the Recording Industry Association of America (RIAA). The Kingston Trio’s version added verses to the 1930 original, giving the otherwise traditional folk song an edgier flair to better appeal to the audience of their generation.

#5 – M.T.A.

On the US Billboard Hot 100, “M.T.A.” peaked at number 15 in 1959. It owes its origins to the 1949 original written by Walter O’Brien for a mayoral campaign in Boston. For the Kingston Trio, Guard starts off with a speech as the cello plays in the background. When the story officially breaks into a full song, it revolves around a character named Charlie who boards a Massachusetts Transportation Authority (M.T.A.) subway car. There is so much Boston lore in the song that it has influenced its mass transportation practices, with nicknames and slogans revolving around the M.T.A. and its named hero.

#4 – Reverend Mr. Black

In 1963, the Kingston Trio released the single, “Reverend Mr. Black,” along with the album, The Kingston Trio #16. On the US Billboard Hot 100, the song reached number eight. John Stewart is credited with his stellar performance in perfectly mixing originality with tradition, which served as a true compliment to the talent of Bob Shane and Nick Reynolds. The song had enough rhythm, blues, and soul to make Reverend Mr. Black a hit, and it also appeared on the US Billboard Hot R&B/Hip-Hop Singles chart at number fifteen.

#3 – Greenback Dollar

In 1962, John Stewart replaced Dave Guard as the Kingston Trio’s lead vocalist, allowing the band to move away from adaptive traditional songs into singer-songwriter cover material. “Greenback Dollar” served as a highlight of the cheerful album New Frontier, which received critical acclaim for its celebration of youth and optimism.

#2 – The Tijuana Jail

In 1959, “The Tijuana Jail” peaked at number twelve on the US Billboard Hot 100. Its melodic performance was loosely based on the old prison song Midnight Special, whose printed origins date back to 1905. Midnight Special has been covered many times over throughout the years. The Kingston Trio performs it as a group of young men who travel to Tijuana for a night on the town, but run into complications with the lawmen of the land who throw them in prison. This song was recorded for The Kingston Trio At Large sessions.

#1 – Tom Dooley

In 1959, the Kingston Trio won their first Grammy Award, thanks to “Tom Dooley” earning the Best Country and Western Recording. Since its original release, there have been several remakes and remixes. The song was also recognized by the National Recording Registry as a seminal recording in the history of popular American music. This was originally a North Carolina folk song that was inspired by the 1866 murder of a pregnant woman named Laura Foster.

It wasn’t the murder itself that was the big story, but the complications surrounding it, including love triangles and other dramatic circumstances that make for perfect movie and songwriting material. The murder, trial, and conviction occurred at a time when a famous Dr. Tom Dooley was making headlines of his own for international humanitarian work. The song Tom Dooley reached number one on the US Billboard Hot 100 and charted at number one worldwide in Australia, Canada, Italy, and Norway.

Updated March 12, 2026

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