As almost everyone knows by now—or at least as she insists in a hit song from her megaselling album Come on Over—Shania Twain doesn't impress easily. But when the singer took home her first Country Music Association Award on Sept. 22—the night's top prize, Entertainer of the Year—she was practically giddy with glee. "I was really prepared not to win," Twain said after the 33rd annual ceremony, held in Nashville's Grand Ole Opry House. "This is the icing and the cherry on the cake."

Twain's sweet-tasting victory capped a night that celebrated country's crossover appeal. The Dixie Chicks—who recently hit the top of the pop charts with the album Fly—won single of the year, best music video and top vocal group. Jewel sang a duet with Merle Haggard, and 'N Sync performed with Alabama. Stylewise, it was a night for urbane cowboys and cowgirls. Faith Hill wore a Valentino ensemble, George Strait traded his trademark jeans for tuxedo pants, and host Vince Gill—who recently shed nearly 40 pounds on a high-protein diet—wore a double-breasted Dolce & Gabbana suit. Still, some country crooners clearly weren't used to playing dress-up. Jo Dee Messina, who won the Horizon Award for career growth, sported a strapless black Calvin Klein dress with a train—which someone accidentally stepped on. "Let's just say I was hanging out," said Messina after the mishap. "Thank God it's not on-camera—though it could help my record sales."

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