The Celebrity: President Barack Obama
What He Said: During an interview in September 2009, the President called Kanye a "jackass" during a segment that he thought was off-the-record. However, an ABC News reporter tweeted about it and, before long, everyone knew what the President really thought about 'Ye.
Did Kanye Deserve It? No. And we're pretty sure that, had President Obama known that the whole world would find out what he said, he would have chosen his words a little more wisely. Being that both he and Kanye are from Chicago, we're sure he doesn't actually have any animosity towards the guy.