Miltons Pimp My Look
Kid used to be a high school basketball player. That’s gotta count for something.
Time to reload the Miltons machine. Send all sob stories to pimpmylook@barstoolsports.com or pimpmydate@barstoolsports.com and help us help you. And you need to send pictures! If you sent an email without a picture resend with one to be considered.
Today’s Contestant
Reader Email
El pres,
This is our friend Dana from Stonehill. Let’s just say that Dana is a
fucking mess. Once the captain of the high school basketball team, soon
after the season was over, Dana started hanging out with the wrong crowd.
Beer and calzone. The kid put on nearly 80 pounds between February to
August, its got so bad that most local sub shops know his name and
already have his order ready before he calls. He just really does not
have his shit together at all, and we feel at fault for it. We constantly
either peer pressure or support his decisions to make us laugh by being
kicked in the balls for 40 bucks, eating a stick of butter, eating a
bakers dozen of dog treats, and countless other dumb shit he’s done for
money or just to make us lauugh. The first time we saw him over the
summer at a party he wore only a jockstrap and covered himself in blue
body paint, and that right there sums up Dana.
Granted, if Dana was to win this contest there is no doubt in my mind he
would immediately spill blue cheese or any dressing on the new clothes he
got, but the kid deserves a chance. So please, El Pres, we beg you, look
in your heart and give Dana some help, he needs all the help he can get.
Or at least throw him a few bucks for a calzone>
Dana’s friends








They have his order ready before he calls huh? Where does he order his food from, The Dionne Warwick House of Pizza?
Body of a lesbian
His name is ‘Dana’ and he wears a cape. 100% has the ghey but he may not know it yet.
after seeing dana, i feel so much better about living in my mom’s basement. that last picture actually made me laugh out loud
Will Milton’s b able to get him a mustache to go with his chinstrap
As Dana’s older sister, I must shamefully agree that he needs this makeover desperately. The times when he has tried to go to job interviews with too short pants and a wrinkled POLO (not even a button up) have been far too frequent. Also, in his glory days he was fit and stylish. Then he discovered Bud Light. He needs to be revived.
looks like a fat version of ashton kutcher