"Like a Boss" is a song written and recorded by comedy hip hop troupe The Lonely Island for their debut studio album Incredibad. The song is a parody of the first official single from Slim Thug's first album Already Platinum, also named "Like a Boss". The song had multiple versions, including an audio-only that did not have the celebrity interviewer and a clean version that was produced in both audio and video. In 2011 it was also subject to a lawsuit from the producers of the song who claimed they never received proper compensation for their work.

"Like a Boss" premiered as a Saturday Night Live Digital Short on April 4, 2009. In the song, Andy Samberg is a businessman, evidently in middle management, having a performance review. The reviewer asks him to describe the things he does in an average day, and does so for the remainder of the song in his trademark aggressive style while repeating the lyric "like a boss" after every activity.

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."

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