At the start of 2009 and ten years into her career, Macy Gray found herself a free agent and on the verge of "The Sellout.” Sure, she sold 15 million albums, scored two Grammy Awards, two MTV awards and with “I Try,” had one of the most successful singles of all time, but after 2007’s Big, she found herself alone, with no one to answer to but herself. Big was the slickest album of her career and she considered going even further away from the true, gritty, whiskey-voice Macy, following instead of leading. In other words, selling out.