Year: 1998
Ranking on the Billboard Charts: No. 1—for three weeks straight
What Will's Doing: Simultaneously jumping the shark musically and demonstrating his unparalleled star power. In this massively popular music video, Will wears a silver velvet sport coat, a jet-puffed Adidas sweatsuit, a pharaoh's headdress, and a tropical forest two-piece get-up—all looks only he could rock, or would even think about rocking. Will Smith is a wardrobe hero. Over an irresistible funk beat, he spits some family-friendly lines and crafts an infinitely catchy hook. But this song has aged like Brendan Fraser and is objectively not good. Still Will’s tip-top charisma carried it as he introduced the world to a little shimmy-hop dance move that he executes at a luau, the Statue of Liberty and a disco-ball-laden house of mirrors.