#24: He Won His First Solo Grammys for “Cry Me a River” and Justified
In February 2004, he won his first Grammys as a solo artist. “Cry Me a River” earned Best Male Pop Vocal Performance, while Justified won Best Pop Vocal Album, confirming that his move away from *NSYNC had been accepted by the industry.

The wins were a major validation of his solo reinvention. He had gone from boy-band standout to Grammy-winning adult pop star in less than two years. But the same month that brought one of his biggest professional victories also brought the most controversial stage moment of his career.
