Like many acts from the Roaring Twenties, this one's name developed out of a close relationship with the first advertiser to sponsor the act on radio, in this case none other than the Happiness Candy Stores chain. The relationship between this stage name and the careers of each of these singers under their own names bobbed and weaved, with recordings by the duo sometimes issued without reference to the Happiness Boys prior to the period during which use of the name became absolutely essential (from around 1925 through 1928). Overexposure, even to such a worthwhile factor as happiness, is apparently the factor credited for this act's slumping record sales in ensuing years.
No other relationship with a sponsor worked out so well for these vocalists, at least in terms of name recognition. For example, they were the Taystee Loafers in the early '30s, a move made on behalf of a bakery that also put up the bread for its own orchestra. In 1936 a razor firm signed on as a sponsor for a show headlining Milton Berle; in this context, the duo was now known as the Gillette Gentlemen, a name the pair continued using as, should it be dared to be said, a shave name until 1939. In none of these cases did the name take on a life of its own, as did the Happiness Boys, in terms of an ironic comment on some vividly glum or gloom-provoking entrance. Say, for example, a group of customs inspectors hops on an international train; someone might say "Oh, it's the happiness boys." With this usage the expression outlived by decades its source in the music business, not to mention the candy store chain. ~ Eugene Chadbourne, Rovi