I'm on a Roll

The music video was released on May 24, 2012. It was directed by Mickey Finnegan and was filmed at the Roosevelt Hotel in Hollywood.[4] American Idol ally Casey Abrams appears in a cameo as a homeless person.

The concept of the video basically follows the lyrical content of the song about luck. It starts off with Stefano waking up in bed and later on having a breakdown with his car. After steering it all the way to a vehicle service to tow away, a stranger with a Ferrari mistakes Stefano for a valet and gives him his keys. As Stefano drives away, a homeless person (Abrams) calls after him. At a traffic stop, he receives exclusive tickets to a private club where he lies down near the pool and gets later invited by a womanizer to join him being massaged by women. As Ben J from the New Boyz appears in the video to rap his solo, Stefano is seen with people who have a pillow fight in the background. Towards the end of the song, Stefano returns the car keys of the Ferrari to the stranger, who gives him a tip. With the tip, Stefano pays the vehicle service for bringing back his car only to remember that the engine of his car is still blown.