Where: MTV Video Music Awards

When: 2006

Early in his career, LL Cool J seemed to be ahead of the pack, starting a few trends we've come to love. But at some point, he may have been overwhelmed by all the fads that came and went, and was unsure of what to rock and what to pass on. Take for instance the bedazzled hoodie he wore to the 2006 MTV VMAs. Maybe he was trying to outshine (literally) 50 Cent, who he arrived with. Either way, the ladies did not love Cool J, or Todd Smith, that night.