It’s not easy being a Black celebrity, especially when it comes to being photographed. It’s bad enough that a stroll down the street or night out becomes front page news, but when you actually pose for a photo it can still come out looking crazy.

Over the years some famous athletes and musicians have been captured on film for main stream publications to mixed effect. Some of the poses, outfits and retouching are enough to get any conspiracy theorist working over time (really, Tiger Woods in a scully? C’mon Son!).

So in this edition of Friday Five we count down the worst photo fails starring LeBron James, Diddy, 50 Cent, Kobe Bryant and Tiger Woods.

5. Tiger Woods, Vanity Fair Magazine, February 2010

For their February 2010 issue Vanity Fair magazine used a 2006 photo of Tiger Woods taken by Annie Leibowitz. The famed photog said she wanted to convey Woods’ “focus and dedication” to his sport. In the midst of his cheating scandal this was probably the worst look for Tiger.  The black scully and dumb bells makes him seem more dedicated to avoiding the Tossed Salad Man in the Rikers Island showers than tee time.

4. P. Diddy, GQ magazine, August 2010

In this photo for GQ “Ciroc” Obama was caught swinging from a chandelier in his underwear. After one too many shots of vodka he imagined he was auditioning for one of these Nike ads:

3. LeBron James, GQ Magazine, September 2010

The newest member of the Miami Heat obviously didn’t heed his boy Jay-Z’s warning in last summer’s “D.O.A”: “you boys jeans too tight, you colors too bright, your voice too light…” Cuz you know he was squealing like a chipmunk with these Uh Oh Sergios cutting off his circulation. Does this mean he’ll be rocking nut-hugging throwback shorts this season too? The worst part is we hear these are actually knickerbockers but the photo was mercifully cropped.*

(*Not true but we thought it was funny)

2. 50 Cent, GQ Magazine, December 2005

How do you treat one of your “men of the year”? You dress him in a sleeveless button up with his tie blowing ever so gently in the wind and make sure he hits you with the “blue steel” Magnum raised eyebrow glare. Derrick Zoolander would be proud.

1. Kobe Bryant, L.A. Times Magazine, Spring 2010

Would you believe us if we said this ensemble was inspired by Tupac Shakur? Go ahead and wipe up the soda you just spit out on your keyboard and then read this statement from the stylist,James Valeri, of the “Kobe as Pilgrim” shoot:

“I was thinking of [rapper] Tupac [Shakur] where I put a band underneath in the hat to make it look hip-hop, but … it translates in a surreal look where it creates a strong image. It’s mixing the inspiration of Tupac and a gentleman with a white hat … a mix of a hip-hop and a conservative look.”


Not even Kobe wasn’t buying that line of reasoning and confessed that he thought the photos were a “little too artsy.”  Kobe went into hiding but we found him here.


50 Cent’s Five Most Flagrant Fouls

Foxy Brown’s Five Biggest Fails

FRIDAY FIVE: Can P. Diddy Really Act?

FRIDAY FIVE: Don’t Ask, Don’t Tell

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