The Swagged-Out Moment: Singing Al Green during a fundraising event in New York City
When It Happened: January 2012
Why It Was So Great: At this point, President Obama has given hundreds, probably even thousands of speeches in front of large crowds. But, still, it's hard to get up in front of a crowd and talk, let alone sing, especially when you're not actually a singer. So, this was a pretty incredible moment. And, to think: His campaign team didn't think he'd do it.