Gary Calamar is one of my favorite music supervisors. He has been the supervisor on numerous hit shows that require many different styles of music. Gary has been, and still is the supervisor for shows like: Entourage, True Blood, Dexter, Weeds, House, and Six Feet Under. 
Here’s a video of Gary and Garth Trinidad (music supervisor) talking about their job on Entourage. It is very telling of how hard it is to get the licensing for songs when on this type of project.