For his second collection of pop standard covers, Michael Bolton doesn't really change his course of action, choosing to sing the songs everybody knows ("Sexual Healing," "Tired of Being Alone," "Let's Stay Together," "Try a Little Tenderness," "(What A) Wonderful World," "A Whiter Shade of Pale," etc., etc.). There are two surprises here, Bobby Caldwell's "What You Won't Do for Love" and Bob Dylan's "Like a Rolling Stone," but they're done up in the same adult contemporary arrangements as everything else on the record. So, Timeless: The Classics, Vol. 2 delivers exactly what you expect: predictable songs, as done by Michael Bolton. In one sense, that makes it stronger than some Bolton albums, since the material is all good, but it also highlights the fact that he isn't as subtle or nuanced a singer as his idols, even though he's grown more powerful over the years. Still, by 1999, that was hardly a revelation, and it seems churlish to complain about Bolton's singing or the predictability of the material, since that all comes as no surprise. Thus, that leaves Timeless: The Classics, Vol. 2 as a solid Bolton album. No revelations, no surprises -- just pure Bolton.
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AllMusic Review by Stephen Thomas Erlewine