The Celebrity: Diddy
When He Got Caught Smoking Weed: In December 2006 at a concert in Toronto
WTF Was He Thinking? We've gotta admit that we weren't exactly "surprised" by Diddy puffing away on what appeared to be a small roach at a concert. But it's still not exactly a good look for him and we have to believe that, with all of the business ventures he's involved in these days, he would never get caught doing this so blatantly again. Then again, who knows? They don't call him Puff for nothing, right?