Video
"Like a Boss" premiered as a Saturday Night Live digital short on April 4, 2009. The video features Seth Rogen, recording over the vocals done by Akiva Schaffer on the single. In the song, Andy Samberg is a businessman having a performance review. Samberg is asked 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 lists activities which are fairly mundane at first, such as talking to corporate headquarters, approving memorandums, remembering birthdays, leading a workshop, and promoting synergy. However, the song takes a turn after he mentions a time that a female subordinate (Debra) he repeatedly hit on rejected him, causing him to "swallow sadness", get hit with a sexual harassment lawsuit and get passed up for a promotion. The ensuing depression leads to him binge drinking vodka and defecating on Debra's desk. The activities Samberg's character describes become more and more bizarre, such as calling a sex line, "cry deeply", attempting suicide, being afraid of committing suicide, vomiting on said subordinate's desk, jumping out of a window, "sucking a dude's dick", purchasing cocaine, crashing his car, "sucking his own dick", eating chicken strips, castrating himself, blacking out in a sewer, meeting a giant fish and "fuck its brains out", turning into a jet, attacking St. Basil's Cathedral ("bomb the Russians"), crashing into the sun, and finally dying, all of which are done "like a boss".
The video ends with Samberg's tombstone being shown (which has the epitaph "He was da Best"), and a skeptical Rogen 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", Rogen leaves the room, annoyed and disgusted.
The video features brief cameo appearances from Saturday Night Live writer John Mulaney as the worker that Samberg micromanages, Casey Wilson as the woman giving Samberg the memo, Kristen Wiig as Samberg's office crush Deborah, Jason Sudeikis as Samberg's boss and Bill Hader as the man on whom Samberg performs fellatio. It also features Jorma Taccone as the man giving him the lawsuit, and Akiva Schaffer selling him the gun. Abby Elliot and Bobby Moynihan can be seen in the video as background dancers.
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