Macy Gray stopped by to promote her new album, "Covered," and perform a song from the record. As Howard expressed surprise that Macy, a distinctly different singer, grew up in relatively banal Ohio and attended a white boarding school, Macy cut in: "I think all boarding schools are white, though." Macy said the sudden and massive success of "I Try" quickly turned to excess: "We don't have to be specific about it but, you know. … I was just partying." She also revealed that she had spent a little time in jail prior to her success with "I Try": "One was a petty theft and then I had a failure to appear. I had 7 traffic tickets and the judge finally sent me away. … like 4 days the first time, 3 days the next."
Macy's Celebrity Hook-Up
Asked about her romantic life, Macy said she went both ways: "It depends on the occasion. On the person. Yeah." Her last female hook-up was a "sorta" famous actress: "It's probably not good [if] I say who it is. … She does movies mostly but I think she's done a couple TVs." Macy then sang--accompanied by a musician banging on a box--a cover of Radiohead's "Creep."