We dug back into the archives and pulled up 14-year-old footage from MTV's 2001 'Icon' special — the very first of which was dedicated to the great Janet Jackson.
Usher, wearing a furry hat that rivaled what Pharrell Williams wore to the Grammys, teamed up with 'Tonight Show' host Jimmy Fallon (Feb. 24) to play a friendly game of 'Catchphrase' with actress Reese Witherspoon (and her lovely asymmetrical bob) and Olympian Mikaela Shiffrin.