“Pass The Bowl” is VH1’s ongoing interview series, wherein celebrities contribute questions to our bowl and fellow celebs later draw a question.

Jamie Follese of Hot Chelle Rae: Have you ever been to jail?

Questlove: No, I’ve never been to jail, however I have an interesting story of how I almost inadvertently went to jail. I’ve been in New York City for a little over two years, and of course, all the weekdays I have Late Night with Jimmy Fallon, and on the weekends, that’s when I do all my Roots activity and all the other activities that take me out of New York so I’ve never had a Saturday off in New York City. I had my very first Saturday off about three months ago, kind of in September.

So, I was bored on a Saturday and I decided I wanted to live like a real New Yorker - I wanted to take my first New York subway ride. Since the 6 train is right outside of my building, I got on the 6 - I thought “Oh, Jennifer Lopez and the 6…” of course, this isn’t the Bronx version of the 6, but more like the Financial District version of the 6. Anyway, ya know, I got on the train - it was fun, or anticlimactic, either/or, same thing. Did what I had to do for that day. I come home and I get off at my stop - which I live in the Financial District, at City Hall, the last stop - and I walk up outside and I thought I was at an art festival because I saw kids beating drums, people doing art work, a bunch of hippie kids with hula hoops.

I’m walking around everything, and this cop comes up to me and says “You know you’re not fooling anybody with that disguise, right?” (I had glasses on and a big hoodie), and he says “If I were you, I’d go over there in like one minute.” And I was like “Ok, what’s about to go on?” [The cop says] “Just hurry up, run over there, trust me.” He’s like “I’m a big fan.” So, I walked over, slightly a block later, and then I turn around and realize I was walking into the heart of one of the very first Occupy Wall Street protests of which they then had 700 people trapped on the Brooklyn Bridge and took them all to jail. It was one of the first arrests - I thought it was an art festival, like who brings a hula hoop to a protest? So, I got fooled. I’m more chagrin that my disguise didn’t work!

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[Photos: Colin Gray/VH1]