Gary Unmarried (2008) - 2x01 - Gary Has A Dream

Gary tries to set an example for his unambitious son, Tom, by pursuing his own dream of becoming a radio sportscaster.
When Tom is pleased with his low scores on a career aptitude test, Allison persuades Gary to set a better example. On a lark, Gary calls his old buddy, Curtis (Keegan-Michael Key), who works at a radio station, and is surprised when he's offered a job...that is, until the frazzled station manager, Sasha (Brooke D'Orsay), clarifies that he's there to paint the building, not report the latest sports news. Meantime, Gary's brother, Mitch (Rob Riggle), escorts Louise to her dance class.