Guest Stars Matt Lauria as Ryan York Lyndon Smith as Natalie Tyson Ritter as Oliver Rome Matthew Atkinson as Zach Jurnee Smollett as Heather Hall Andrew Joseph Barr as Band Member #4 Ryan Wells Peterson as Band Member #3 Leonard Jay Jackson as Band Member #5 Dennis L.A. White as Mista Ray Craig S. Ellis as Entourage Member #3 David Douglas as Arrison Turner Destin Davis as Lil Ray Ian Kahn as Harry Lerner Nigel Lawes as Entourage Member #2