Every time I think he's gone as low as he can he goes lower.

What are ways you can think of that he could be even worse?

Mines:
His voice and eyes could change into Judge Doom's from Who Framed Roger Rabbit. https://www.youtube.com/watch?v=qtKOPF0NyHg#t=47s

That's about the only way I think he could get worse.

How about you?

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Gone: My Discogs collection for The Roots:
http://www.discogs.com/user/tomhayes-roots/collection