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Jake Gyllenhaal ‘The Princess He-Man of Persia’

Pretty On The Outside - Jake Prince of Persia Gyllenhaal

It has been awhile since we heard from our buddy David Gilmore at Pretty On The Outside, but he sent over his latest illustration today. In it he depicts Jake Gyllenhaal as muscle hero ‘He-Man’ from back in the day of ‘Masters of the Universe’. He was inspired by photos (see below) he saw of Gyllenhaal in character for the film Prince of Persia: The Sands of Time.

Jake Gyllenhaal as Prince of Perfection

That homely looking creature next to Jake is his girlfriend Reese Witherspoon. She looks like she is having a blast!

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Jamie Lynn Spears is Britney in Training

POTO: Jamie Lynn Spears in Training

David from Pretty on the Outside sent over enhanced photo collage of Jamie Lynn in (Britney Spears) Training. This story continues to make me a bit sad. I would have thought just being witness to her sister’s behavior would have at least inspired her to keep her prescription current or to stop by the drug store before shedding her floss.

More of David’s Work

POTO: Posh Pokey ChristmasDavid Beckham's Christmas PackageDavid Beckham's Golden BallsPosh Spice Pokes Out the Fridge

Merry Poshmas from Victoria Beckham

Victoria Beckham Poshmas

David from Pretty on the Outside sent over this illustration  he did this morning of Victoria Beckham wishing everyone a very pokey Merry Poshmas!

More of David’s Work

David Beckham’s Brief(s) Christmas Package

POTO David Beckham Christmas

David from Pretty on the Outside sent over this illustrative Christmas card featuring David Beckham and spoofing his most recent ad for Emporio Armani underwear. Merry Beckmas!

David Beckham Emporio Armani

David Beckham Emporio ArmaniPOTO David Beckham Christmas

David Beckham’s Golden Balls

POTO David Beckham’s Golden Balls

David from Pretty on the Outside sent over this illustration of David Beckham’s ‘Golden Balls’, which is a reference to how Elton John greeted Beckham, when kissing him on the cheek last week, at a football party last week.

Posh Spice Pokes Out the Fridge

POTO: Posh Spice Pokes Out

David from Pretty on the Outside sent over this illustration of Victoria ‘Posh Spice’ Beckham poking into her refrigerator to show what she puts into that ‘oh-so-healthy’ body of hers.

Lindsay Lohan Demonstrates How to ‘Blow’ $7 Million

Pretty on the Outside: Lindsay Lohan Blows

David from Pretty on the Outside illustrates how Lindsay Lohan was able to blow $7 million dollars in the past year.  If Lindsay had a brain, or a good accountant, she would only be snorting the interest on $7 million bucks.

At a very modest 6%, the interest on $7 million dollars would be $420,000.  That breaks down to  $1,150.68 a day for cocaine.  As a human, if you can’t live on $1,150.68 dollars a day for anything and everything then you probably deserve to lose it all.

O.J. ‘Scarecrow’ Simpson Wishes He Had a Brain

O.J. Scarecrow Simpson Wishes He Had a Brain

David from Pretty on the Outside with his latest caricature take on O.J. Simpson humming “…if I only had a brain.” as he was being arrested and whisked away by the Las Vegas Police Department over the weekend for armed robbery.

See more of David’s comical illustrations here

Britney Spears Past Casts Sexy Shadow

Britney Spears MTV VMA Performance so not pretty on the outside

David from Pretty on the Outside sent over his latest caricature of Britney Spears failed attempt last night to re-energize her career at the MTV Video Music Awards.

It is safe to say that Britney is a shadow of her old sexy self or perhaps her shadow is just sexier than she is nowadays.

Yikes!

Amy Winehouse as Wonder Woman

Amy Winehouse as Wonder Woman

David from Pretty on the Outside is the hottest caricaturist of Hollywood celebrities. After Amy Winehouse went nutso on her husband Blake Fielder-Civil earlier in the week. So hopefully she is feeling Wonder Woman or at least the King and Queen of Blake’s castle. PS: There is nothing more silly than a man with a hyphened last name.

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Warm, Fuzzy, and Cute Zac Efron

Zac Efron is Pretty on the Outside

David from Pretty on the Outside having some fun with High School Musical’s Zac Efron. Zac is in position to becoming one of Hollywood’s leading heart throbs if he can keep his hands off Paris Hilton.

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Pete Doherty the Ugly Partying Rock Star

Photo: POTO Pete Doherty

David from Pretty on the Outside with another of his caricatures. This one is of pseudo rocker Pete Doherty. He doesn’t look anything like a rock star but he no doubt parties harder than anyone this side of Keith Richards.

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