Climb Every Billboard

S6 E20: Larry's boss, Wainwright (F.J. O'NEIL), tells Larry (MARK LINN‑BAKER) that he finally liked an idea that Larry suggested on one of the many memos he slipped under his boss's door. The idea is that someone live on a billboard until the Chicago Bulls' losing streak is over. Wainwright expects Larry to find someone to do it or do it himself, despite the fact that it's in the middle of winter.