This two-fer combines two albums Andy Williams recorded in his early thirties in the late '50s, a time when he had carved out a career as a maker of hit singles and was trying to make a transition into the album market. Both collections have concepts. Sings Steve Allen features 12 songs by a Williams mentor, the famous talk show host who gave him a national late-night forum for two years in the early '50s, providing the springboard for his move into records and his own TV shows. Allen was a minor pop-jazz tunesmith as well, and Williams' payback effort displays many of his pleasant songs with appropriately nightclub-style arrangements. Two Time Winners refers to songs that have been popular in two different eras, for example, Williams' own 1958 hit revival of "The Hawaiian Wedding Song." He essays some of the big hits of the late '50s, such as "Blueberry Hill" and "Love Letters in the Sand." But there are quite a few ringers that didn't quite fit the concept and most of them -- "Sweet Leilani," "Blue Hawaii" -- are songs of the 50th state, suggesting that Williams may have started out to make a Hawaiian album in the wake of "The Hawaiian Wedding Song," then thought better of it. The albums display two different aspects of Williams' singing talent at a time when he was on his way to becoming the mature crooner of the early '60s.
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AllMusic Review by William Ruhlmann