Flying on Obama's private plane. Obama looked at Oprah, chuckled and said, 'You know, I could throw a $1,000 bill out of the window right now and make somebody very happy. Oprah shrugged her shoulders and replied, 'I could throw ten $100 bills out of the window and make ten people very happy. Michelle added, That being the case, I could throw one hundred $10 bills out of the window and make a hundred people very happy.. Hearing their exchange, the pilot rolled his eyes and said to his co-pilot, 'Such big-shots back there. I could throw all of them out of the window and make 56 million people very happy.'