He first lists activities which are fairly mundane, such as communicating to bigger bosses in corporate headquarters, approving memorandums, remembering birthdays, leading a workshop, and promoting synergy. However, the song takes a foul turn after he mentions his female subordinate Deborah, whom he repeatedly pursues, rejecting him, causing him to "swallow sadness", face a sexual harassment lawsuit and be passed up for a promotion. The ensuing depression leads to him binge drinking vodka and defecating on Deborah's desk. The activities Samberg's character describes become more and more bizarre, such as calling a sex line, "cry[ing] deeply", demanding a refund, attempting suicide with a gun only to back out in fear, vomiting on Deborah's desk, jumping out of a window, "suck[ing] a dude's dick", purchasing cocaine, crashing his car,"suck[ing] his own dick," eating chicken strips, castrating himself, blacking out in a sewer, meeting a giant fish which he evidently "fucks its brains out", turning into a jet, "bombing the Russians", crashing into the sun, and finally dying. Everything described is done "like a boss. " It ends with the reviewer trying to confirm some of the more bizarre events with Samberg, who confirms that he does daily chop off his testicles and die, but denies ever having said he fellates himself. While Samberg then keeps repeating the words "I'm the boss," the reviewer leaves the room, understandably annoyed and disgusted. The video ends with the giant fish delivering the final words "like a boss. "