Ryan Cabrera

Managed by Ashlee and Jessica’s father Joe Simpson, Ryan Cabrera has undergone quite a transformation since he hit the music scene in 2004 with his hit “On the Way Down,” which peaked at number 15 on the Billboard Hot 100.

In 2006, Cabrera released a single “I Will Remember You,” which was featured in a promotion for Will and Grace‘s series finale and as the elimination song for the 2007 season of So You Think You Can Dance.

Cabrera dated Hills star Audrina Patridge for four months in early 2010, but the couple reportedly called it quits as a result of Cabrera’s partying lifestyle.