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.

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

go on reading »

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

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 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 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.

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.

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.

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

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! Brit exposed her nasty again last night after the show! (NSFW) Attention Whore!

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.

go on reading »

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.

go on reading »

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.

go on reading »

David from Pretty on the Outside created this great caricature centered around our post yesterday about the video tape Kevin Federline has of Britney Spears hitting him on the head with a frying pan and hurling an ash tray at him.

go on reading »

David from Pretty on the Outside’s latest creation claims just how ‘duckalicious’ Jenna Jameson and Daffy Duck are together. The ever thinning Jameson was spotting looked a bit like Skeletor on the beach over the weekend.

Amy Winehouse and her new hubby are in rehab for their heroin and cocaine addictions. A great way to spend a honeymoon.

Vampy trampy Amy Winehouse and new chav hubby Blake Fielder-Civil had a real rock-and-roll honeymoon –- a trip to rehab for alleged heroin and cocaine addiction. Party on!

Whinin’ Winehouse and Doherty-lite, according to a report in the Mirror, agreed to attend rehab after watching their fathers come to blows over their supposed shared addictions.

The number of celebs to go to rehab continues to increase and the number of success stories from rehab remains at ZERO!

photo: POTO

David from Pretty on the Outside with another great caricature. This time featuring the Major League Soccer’s marketing toy that is David Beckham.

POTO’s David Gilmore created this illustration of Tom Cruise with Katie Holmes trying to outdo his man-crush David Beckham W magazine cover with his wife Victoria Beckham.
go on reading »

Another one of David Gilmore’s perfectly hilarious illustrations. Pregnant jailbird Nicole Richie looking rather hot in her stripes.

More Funny POTO Illustrations

• Pregnant Jailbird Nicole Richie
• Rosie Discusses Whoopi’s Hiring on her Blog
• Lindsay Lohan Freckled Felon (Funny)
• Paris ‘Lochness Monster’ Hilton
• Tara Reid Pretty on the Outside

David from Pretty on the Outside’s latest rendering or how Rosie O’Donnell’s blog is likely to look now that ‘The View‘ has hired Whoopi Goldberg to replace her.

More Funny POTO Illustrations

• Pregnant Jailbird Nicole Richie
• Rosie Discusses Whoopi’s Hiring on her Blog
• Lindsay Lohan Freckled Felon (Funny)
• Paris ‘Lochness Monster’ Hilton
• Tara Reid Pretty on the Outside

David from Pretty on the Outside sent over his latest caricature this evening. On a day like today you know it can’t be about anyone other than the ‘Freckled Felon’ Lindsay Lohan.

More Funny POTO Illustrations

• Pregnant Jailbird Nicole Richie
• Rosie Discusses Whoopi’s Hiring on her Blog
• Lindsay Lohan Freckled Felon (Funny)
• Paris ‘Lochness Monster’ Hilton
• Tara Reid Pretty on the Outside