Cuddly Dudley sounds like a name out of a very different time in popular culture, and it -- and he -- was. Born Dudley Heslop in the 1930's, he became a professional singer in the early 1950's, and started recording in the mid-1950's for Oriole Records, a family-owned concern and perhaps the smallest of England's major labels (later bought out by the American Columbia Records label, which slapped the CBS Records name on its pressing plants, studios, and offices). He worked with the Charles Ross Orchestra, singing distinctly in a big-band idiom, just prior to rock 'n' roll's starting to make inroads into British listenership. He made the jump to the new music and Heslop had a special advantage and status when he began making the transition, in that he was black. Heslop had a strong voice and could handle rock 'n' roll -- he was also slightly stout and rotund, resembling a very young Willie Dixon, and he decided to play to this appearance by taking on the professional moniker of "Cuddly Dudley" (some sources spell it "Cuddly Duddly"). He was presented by his manager, Guy Robinson (who also handled Johnny Kidd & The Pirates), as England's answer to the Big Bopper. With his big voice and flashy suits -- highlighted by large, ornate ties -- he fit the role and then some, and he did have a good rock 'n' roll crooner's voice.
He was probably already England's top homegrown black rock 'n' roll singer -- not that there a lot of competition -- when he got his big break. Producer Jack Good had put together a television rock 'n' roll showcase called Oh Boy!, and was in the market for resident artists -- Cuddly Dudley ended up as one of the latter, right alongside Cliff Richard, Marty Wilde, and other new UK rock 'n' roll stars. He became a star on the show, and cut a single of "Later" b/w "Lots More Love" in 1959 on EMI's HMV imprint, and he made it onto the Oh Boy! tie-in LP that was issued with two of his featured songs. By 1960, he was fronting his own combo, an all-black band billed as the "Embraceable Four" (to tie-in with "Cuddly Dudley"), and he released a single covering Chuck Berry's "Too Pooped To Pop". He later had a white band called the Redcaps backing him. They released one single together, entitled "Sitting On A Train", but never made the charts, and the Redcaps' bassist and drummer, Johnny Spence and Frank Farley, later became part of Johnny Kidd & The Pirates. By the time of the Merseybeat boom, he was working in cabaret and recording for Pye Records' Piccadilly imprint, as well as his old friends at Oriole, and by 1963/64 had switched his sound to ska and bluebeat, which had found significant audiences in England. He disappeared from the pop music scene in the mid-1960's. Since then, his name has turned up in various accounts of British rock 'n' roll's first half-decade and his songs have shown up on reissues, principally associated with Oh Boy!.