Toofer and other TGS staff members don't look thrilled in this scene. It's from the episode "Winter Madness."
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James "Toofer" Spurlock is a character on 30 Rock.
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30 Rock Quotes

Jack: Never go with a hippie to a second location.
Liz: I need to do that thing that rich people do where they turn money into more money. Can you teach me how to do that?
Jack: With my eyes closed.

Hey, nerds! Who's got two thumbs, speaks limited French, and hasn't cried once today? [pointing thumbs at self] This moi.

Liz