[2][3] Born in Mahlabathini, Natal, Wakefield was educated in South Africa, then traveled to England, where he began acting with a Shakespearean repertory company.

[3] Wakefield created the stage persona of a nervous upper class young man, customarily dressed in full dinner suit and habitually carrying a cigarette.

He developed a distinctive stuttering mode of speech featuring tortuous syntax, malapropisms, spoonerisms, dropped words and unfinished sentences which he used to disguise his satirical observations, wry sarcasm and clever double entendres.

[11][12] He made regular appearances at the Savoy Theatre, the Berkeley, the Ritz, Cafe de Paris, Churchill's and other leading London venues.

He was booked to open at the Rainbow Room in New York City three weeks after the outbreak of World War II, but chose to remain in England, where he served in the R.A.F.