Tonight, former NYC mayor and the 9th richest man in the world Michael Bloomberg will make his debut on the Democratic debate stage. Bloomberg has already pledged to open up his checkbook come November for WHOEVER the democratic candidate ends up being. This could set up a really interesting dynamic of candidates hammering Bloomberg but in a “nice” way so they can still get the payoff if/when that day comes.

For lots of non-New Yorkers, this could be a first look at Bloomberg that isn’t a carefully and expensively crafted campaign ad. So what is the word on Bloomberg and his style? “Stiff”, “easily-riled” and “prickly” are some of the adjectives that the NYC media has used to describe him. This could be good.

Until the debate, here are a couple of times then-Mayor Bloomberg stepped out of his comfort zone…by doing painfully self-conscious show tunes. Seriously, in this parody of “Under the Sea”, Bloomberg looks like a man who is ONLY doing this because a crazy musical theater-loving Mafia Don has kidnapped a loved one and is forcing him to sing and dance or he’ll start receiving fingers in the mail.

Woof. That’s hard to watch. Here’s another theatrical foray of Mike Bloomberg threatening to run for president all the way back in 2007.

By the way, those aren’t ropes that are making him fly. He’s actually of such a slight build that was a mild updraft that caught the umbrella and lifted him to the rafters.

Bonus Fun Fact: Michael Bloomberg has bought so much advertising on this station that I’ll finally be able to get those calf implants I’ve always wanted!