11. Justin Timberlake (2006)
Even in the pre-"Dick in a Box" era, Justin Timberlake was taking chances. The Cyborg&B of "SexyBack" is one of the weirdest Number One singles in history — and it had yet to start its seven-week chart-topping run. With little more than a grey suit, black vest, white sneakers and hair shaved down to stubble, Timberlake dominated the stage during a FutureSex/LoveSounds twofer starting with "My Love." A dapper Timbaland (mostly) synched into step for "SexyBack," brushed some imaginary dirt off JT's shoulder, and they closed it down with beatboxing. Unlike a lot of these performances, there weren't too many pyrotechnics beyond his dancing: The futuristic sounds coalesced perfectly with old-school showmanship.