Like role model George Michael, Robbie Williams has attempted to convert teen-idol success into a pop-star career, and the going hasn't been easy. Williams broke up the post-New Kids/pre-Backstreet English boy band Take That in 1995, and after two successful U.K. solo albums compiled a de facto best-of, 1999's The Ego Has Landed. Assembled for the U.S. market, the disc met with decidedly measured interest despite its Top 10 hit, "Millennium." Working with former World Party keyboardist Guy Chambers, Williams' solo career has consisted of overt attempts to become a thinking person's chart-topper. The problem? Now isn't a particularly good time for pop that requires thought. Moments in which Williams sacrificed smarts for success ("Angels," which recalls late-period Elton John, is a notable example) sounded more calculated with each listen, while his more challenging material left some listeners puzzled. The largely pleasant new Sing When You're Winning offers up more of the same, material for an alternate-universe Top 40 aimed at twentysomethings rather than the orthodontia crowd. The first single, "Rock DJ," combines a Scary Monsters-era Bowie beat with an odd half-rap and a soulful chorus that neatly sums up what Williams does best, dangerously treading the line between silly and irresistible. Those still interested will probably enjoy the remainder of Sing, including the Kylie Minogue duet "Kids," the pensive "Better Man" (which, frighteningly, wouldn't sound out of place on a Monster Ballads album between "More Than Words" and "To Be With You"), and the self-descriptive "Love Calling Earth." The thinking person's pop star? Not yet. The thinking person's guilty pleasure? Certainly.