7th Season Idol Winner, David Cook, broke the Billboard record of having the most songs debut in the Top 100 in one week. Miley Cyrus was previously the recipient of this title. Cook made headlines when he attended the 12th Annual Race for Hope 5k Run/Walk and announced that his brother had just passed from brain cancer the day before. Cook admits dating fellow Idol contestant, Kimberly Caldwell back in 2008. They broke up the same year.