In February 1959, Andy Williams reached the Top Ten with his revival of the 1926 copyright "The Hawaiian Wedding Song," and it inspired the concept behind this album. The title of Two Time Winners refers to songs that have been successful twice. The idea allowed Williams and Cadence Records head Archie Bleyer (here doubling as orchestra conductor) to include Williams' covers of some recent hits, among them "Sail Along Silv'ry Moon" (Top Five for Billy Vaughn, 1957, and for Bing Crosby, 1937), "Twilight Time" (number one for the Platters, 1958, and Top 20 for the Three Suns, 1944), "So Rare" (Top Five for Jimmy Dorsey, 1957, and for Gus Arnheim, 1937), "Blueberry Hill" (Top Five for Fats Domino, 1957, and number one for Glenn Miller, 1940), "Love Letters in the Sand" (number one for Pat Boone, 1957, and Top Ten for Ted Black, 1931), "My Happiness" (Top Five for Connie Francis, 1959, and for Jon & Sandra Steele, 1948), and "Near You" (Top Ten for Roger Williams, 1958, and number one for Francis Craig, 1947). But not all of the 12 tracks fit the concept exactly, and there was evidence that Williams and Bleyer may have started out to do an album of Hawaiian music before changing gears. The only person to score a hit with "Blue Hawaii" had been Bing Crosby in 1937 (though Elvis Presley would revive it a couple of years after this album was recorded). Crosby alone had also been responsible for another Hawaiian hit, "Sweet Leilani," though one could perhaps stretch a point and say it was a "two time winner" in the sense that it was both a chart success and an Academy Award Best Song recipient. Anyway, Williams continued to prove himself an effective and versatile singer capable of bringing off such lightly rocking or exotic revivals.
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AllMusic Review by William Ruhlmann