A few days ago Jimmy Fallon did a series of hilarious impersonations during the Super Bowl special, auditioning as the following pop stars for the Super Bowl halftime show:

Justin Bieber - Baby
Bruno Mars & Eminem - Lighters
Josh Groban - You Raise Me Up
Taylor Swift - You Belong With Me
DJ Pauly D
LMFAO - Sexy and I Know It
Tebowie (David Bowie + Tim Tebow)

Nearly 10 years ago, Jimmy Fallon did the similar thing as the host of The 2002 MTV Video Music Awards, parodying some of the hottest pop songs of that year: (the show marked Avril Lavigne's first big night, Christina Aguilera embracing the "dirrty" side of the force, and Justin Timberlake's breathtaking debut solo performance, etc.)

Eminem - Without Me
The White Stripes - Fell In Love With A Girl
Avril Lavigne - Complicated
Dave Matthews Band - Everyday
Nelly - Hot In Herre
Enrique Iglesias - Hero
James Brown - Get On Up