The Life and Times of Tim (2008)

This edgy animated sitcom follows the cringe-inducing misadventures of Tim, a twentysomething slacker whose life skips from one blown chance, awkward misunderstanding and ill-advised scheme to another. Enabled by his long-suffering girlfriend, Amy, and his prostitute next-door neighbor, Debbie, Tim deals with especially sticky escapades involving his epically bizarre boss, The Boss.