“That One Night” – The Hunted (from the US version of “The Office) (2008)

To identify the most cringe-worthy moment of one of the most crigne-worthy episodes of the US version “The Office” is, I realize, a bold task.  But this song, written for Michael Scott’s girlfriend / ex-boss Jan Levinson by her former assistant, is beyond creepy … and funny.   We first see Levinson’s assistant Hunter on the episode where Jan is getting fired (“The Job”), and as she hugs Hunter, tells him “”Good luck with your band,” adding “Don’t let them change you.”  Well, this is the payback … a song dedicated to the night where Jan allegedly made Hunter a man.  The fact that Jan plays this song wistfully in front of her current boyfriend (Michael) while trying to dance with another man is an extremely queasy and funny moment.   The fact that Hunter named his band “The Hunted” speaks volumes.

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