Broke* (2011)

Broke* is a feature length documentary film written and directed by Will Gray. The film is an autobiographical account of Gray's attempt to break into the music business. Broke* features appearances by Kelly Clarkson, Seth Godin, John Legend, Buddy Miller, Isaac Slade of The Fray, and Don Was.

More at Wikipedia.

Cast:

• Audrey Ryan of Folkwit Records
• Beka Tischker, Manager, Advanced Alternative Media
• Bob Donnelly, Attorney
• Buddy Miller of New West Records
• The Candles
• Chopmaster J
• Kelly Clarkson
• Trent Dabbs
• Will Dailey
• Emily Hope Price, Independent Artist
• The Fieros
• Seth Godin
• Will Gray
• Damien Horne
• Hymns, Independent Artist
• Ian McEvily, Manager, Rebel One Management
• Isaac Slade, Epic Records
• Nathan Johnson
• John Legend, Columbia Records
• Joonie, HitClub Entertainment
• Lee Bailey, owner, EURweb
• Lonny Bereal, HitClub Entertainment
• Mike Grimes, co-owner of The Basement
• Nathan Lee, independent artist
• Nicholas “Aqua” McCarrell
• Steven Ivory, music journalist
• Don Was
• Will Gray, himself