Where does the meme like a boss come from? The original boss may be the rapper Slim Thug, whose 2005 track “Like A Boss,” from the album Already Platinum (which never went platinum), lists the myriad tasks he performs like a boss (e.g. “When I floss / like a boss”). In 2009, Andy Samberg of Saturday Night Live and The Lonely Island made a video entitled “Like A Boss” featuring Seth Rogen, which describes further boss-like activities (e.g. “promote synergy / like a boss”). This is part of a complete episode.