The Three Most Annoying Aspects Of Justin Timberlake's Latest Jessica Simpson Impersonation [Oooh What A Little B-Shot Can Do For You]

As we’ve noted in the past, Stinky master of predicting the future of love sounds Justin Timberlake isn’t quite on the level of Richard Pryor or Lenny Bruce when it comes to comedy routines. After failing to elicit laughs at the Rock ‘n Roll Hall of Fame earlier this year, and trying out the rarely-cute attempt to evade relationship questions on Leno, Timberlake is evidently still fixated on proving he’s just bursting with comedic prowess. His latest stunt? Impersonating Jessica Simpson at the Timberlake-hosted ESPYs, airing this Sunday, by wearing a cheap blonde wig, standing in front of a cut-out of her daisy dukes, and making frightening facial expressions supposedly meant to resemble the time-traveling Tony Romo groupie. The good news? Despite these photos doing little to inspire even a smirk from us, we feel the need to point out Timberlake’s impressively hilarious impersonations of the past on Saturday Night Live, both as a tweaked out awesomer-than-thou Ashton Kutcher, and a far better Jessica Simpson impression years before:

1) Justin Reportedly 'Had His Idols Rolling In The Aisles': Not only do we doubt this, but the idea of Michael Jackson, currently being wheeled around Vegas for his ailment du jour, and Prince, hardly a "sports junkie" like Justin, falling off their auditorium seats in some sort of laugh attack just isn't an idea we can properly picture.

2) Using Truly Pathetic Lines: While in faux-drag, Us reports that Justin had the crowd in hysterics due to NippleGate-referencing jokes like "I wanted to be the only guy at a football game to get to second base!" And, while in Simpson mode, (s)he pondered possible Bennifer-esque nicknames such as the but-gusting "RoJo" or "Tessica." Howl!

3) Drag Does Not Become Him: The sight of Timberlake in a wig accompanied by a five-o-clock shadow and ungroomed mangy brows, not to mention double Ds and Jessica's thick Daisy Duke legs, is no picnic.

But! To give Timberlake mildly well-deserved credit in the jokester department, we fondly remember his "I'm Awesome!" Punk'ing Punk'd skit from his 2003 hosting gig at SNL, plus a classic bit from the same evening in which a Simpson-imitating Justin played dumb blonde to the Nick Lachey-imitating Jimmy Fallon. Even a simple throwaway joke like "Nick" telling the audience "She can't even cure a ham." Justica's response? "Aww, is the ham sick?" was made funny due to Justin's steady confidence post-solo breakout:

[Photo credits: Just Jared]

Published 7/17/08 by

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