The Swagged-Out Moment: Referring to Kanye West as a "jackass" after the 2009 MTV Video Music Awards
When It Happened: September 2009
Why It Was So Great: Although the President called Kanye a "jackass" off the record, the recording was released almost immediately. And, even though he didn't mean for the world to know his feelings on Mr. West, it was still pretty cool to hear that the President had a strong opinion on what 'Ye had done to Taylor Swift at the 2009 VMAs. It was even cooler to hear him say it again during an interview with The Atlantic a short time later.