The music video was directed by Bill Paladino and was released on May 23, 2012. It was filmed in Pittsburgh, Pennsylvania at multiple locations, including a ballet studio, the city suburbs, a private party at a bar, and a soccer field. It features a ballerina played by Katie Schurman, a construction worker played by Michael Major and a soccer player working in each of these roles, and later celebrating at the bar. Wiz Khalifa appears wearing clothes as a hippie, paying tribute to Jimi Hendrix. Multiple Taylor Gang members make cameo appearances as well.
The official remix featuring Lil Wayne and Young Jeezy was revealed through his Twitter page on August 25, 2012.Drake was originally supposed to have a verse on the remix but that didn't come to fruition as he never submitted his verse.
Marco Rubio mentioned the song during March 2013 Rand Paul Filibuster of CIA Director. Rand Paul's filibuster tried to block President Obama's choice of John O. Brennan as CIA chief. Calling Wiz Khalifa a modern poet, Rubio mentioned the rapper by name and stated that he was reminded of his song "Work Hard, Play Hard. "You look at the time, I think it's a time when many of our colleagues expected to be home, back in the home state playing hard," Rubio said, "but I'm happy we're here still working hard on this issue."