Year: 2005
Ranking on the Billboard Charts: No. 7
What Will's Doing: He’s rocking layered wife-beaters, red forearm bands and a personalized, auto-mechanic jumpsuit. To be fair, Smith flows effortlessly over a stomp-clap beat, but comes off very "Old Man Yells at Cloud" when he complains about scantily-dressed women and fans downloading music rather than frequenting record stores. He proved he could still spit and purged the last remnants of his musical ambitions on Lost and Found. But nobody really cared.