Becoming Pony Boi (2009)

From Hollywood Geek, to the Hugh Hefner of Hip Hop. The comedic journey of the most famous rap superstar you've never heard of. Hollywood director Jackie Stein, decides to live out his childhood dream of becoming a rap superstar. In the vein of This is Spinal Tap, we follow his journey as he transforms himself from Hollywood geek, to the Hugh Hefner of Hip Hop called Pony Boi. Pony Boi makes an album, a video featuring Dabrat, gets more women than he imagined and lives his dream, but at what cost? We see Pony Boi transform from corporate everyday guy into pumped up, tattooed, slang speaking Rap artist getting swept up in the music scene, it's fans and the chaotic journey it takes to become famous. During Jackie Stein's transformation into a rapper Pony Boi, Amy Weber (his loyal longtime girlfriend) is completely unaware of his new persona, or even his location. Amy, as well as his parents Rita and Len Stein, thinks he's off writing another movie in New York. His new found fame and fan adulation creates many fleeting love interests along the way, then we watch his descent from notoriety into total collapse as he tries to climb the fame ladder, spending all his money on touring, promotions and creating the Pony Boi hype. Largely improvised, 'BECOMING PONY BOI' looks and sounds like a "real" mockumentary, with a couple of key differences, Myers actually releases a worldwide chart hitting album, gets tattooed, does a music video with Danny Moder starring DaBrat, and blows every cent he had ever earned.