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The Jesters are best known for their soaring falsetto-driven minor hit "So Strange" and for their cover versions of the Chantels' "The Plea" and the Diablos' 1954 classic "The Wind" (which had established Nolan Strong's place as an R&B legend). The latter barely managed to chart on Billboard's national chart (number 110 on June 20, 1960), but the Jesters' addition of a fifth harmony vocal part definitely added to the song's enduring beauty. Like many acts before them, they exemplified the New York City vocal group sound of the mid-'50s. They were particularly influential on mostly white, early-'60s vocal groups like the Excellents and the Imaginations.
The Jesters formed in 1956, when Lenny McKay (lead), James Smith (aka "Jimmy") (second tenor), Leo Vincent (baritone), and Noel Grant (bass) were still attending Cooper Junior High School in Harlem, located on 120th Street. The group often practiced under a nearby elevated railway station. The group got their name from Grant after his favorite movie, Danny Kaye's The Court Jester.
Meanwhile, 17-year-old Adam Jackson was attending Samuel Gompers High School in the Bronx and was singing in a quintet called the Continentals. His group managed to land a TV performance later that year singing the Flamingos' "I'll Be Home." In early 1957, Jackson joined up with the Jesters. Jackson and McKay soon began sharing the lead vocal duties (Jackson's falsetto was often the highlight to McKay's lead) and both were songwriters, but it is generally considered that McKay was the group's leader. They eventually auditioned for and were turned down by Columbia Records, but that didn't deter them. The group performed at the Apollo amateur night contest and after winning first prize three times, they were spotted and signed by Winley Records owner Paul Winley.
The Jesters' first single was "So Strange," a drowsy doo wop song which became a local New York favorite and even charted on a variety of East Coast disc jockey lists. On July 15th, the single had built up enough steam to jump onto the lowest position of Billboard's national pop chart for a single week, landing at number 100.
Their next single was a classic rhythm ballad that is often considered the epitome of mid-'50s New York doo wop: "Please Let Me Love You." Once again, McKay took the lead tenor and Jackson the falsetto. By that time, the Jesters had begun touring the chitlin circuit. When they returned to the Apollo for shows alongside labelmates the Paragons and a stellar group of R&B stars — Ben E. King, Ruth Brown, Jimmy Jones, the Olympics, and Dante and the Evergreens — they were consummate pros. Their third single for Winley was a solid remake of the Chantels' ballad "The Plea," which climbed up the charts to number 74 pop in March 1958. (Incidentally, the arranger for all of these recordings was former Pearls and Valentines' vocalist David Clowney. He became more well-known some 14 months later under the name Dave "Baby" Cortez when he struck instrumental gold with his own number one hit, "Happy Organ," in 1959).
In June 1958, the Jesters dropped their fourth and final single for Winley with the original lineup, this one another two-sided classic, "Now That You're Gone," but by then, the group was splintering: McKay and Grant left and Vincent had been drafted. To replace them, Jackson and Smith brought in baritone Melvin Lewis (the Climbers) along with his brother Donald Lewis on bass.
In the meantime, Paul Winley noticed his release schedule of label issues seemed to always have a Paragons single followed by a Jesters single. This, along with the increasing popularity of "battle of the groups" shows and street corner sing-offs, gave him the idea for the classic album featuring two of his vocal groups dueling it out. Issued around 1959, The Paragons Meet the Jesters LP — with its cover depicting members of a hotshot street gang — was one of the first rock & roll compilation LP's ever conceived. It sold very well on the East Coast.
By May 1960, this new Jesters quartet had its first single, a revision of the Diablos' 1954 classic "The Wind." It was an excellent version and scored number 110 on Billboard's June 20, 1960, national pop chart. Like the original version, this one featured the group chanting the words "blow wind" in harmony behind Adam Jackson's ethereal tenor lead and smooth-as-silk talking bridge. Their last two singles were not of the caliber of their earlier 45s and never charted. The Jesters did some backup work for other Winley artists, namely Charlie White of the Clovers ("Nobody's Fault but Mine" in 1958) and Ann Fleming, Winley's wife ("Jive Time Baby" in 1960), and during the early '60s, even backed Ben E. King onstage at the Apollo.
The group's main man — Lenny McKay — never returned and that may be part of the reason that the Jesters never were able to attain the heights that many of their contemporaries did. They never really ever broke up, working occasional gigs throughout the ensuing decades and often performing in a routine based on their LP with the Paragons. In 1974 they became a quintet when Adam Jackson's brother Ronald Jackson (former lead of the Youngtones, Xtra Records, 1957) joined up.
In 1991, the group was still around, with Adam Jackson on lead, Ronald Jackson on tenor, Melvin Lewis on baritone, Donald Lewis on bass, and Marshall Cherry on second tenor. The group continued to perform well into the decade and were still going strong at the beginning of 2000. Along with the aforementioned Paragons, the Vanguards, Diablos, and the Five Keys, this group's wonderful recordings reveal perhaps the best use of falsetto leads (artificially produced tones in an upper register beyond the normal range especially of a tenor) of the doo wop era.