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

Oh, poor baby. Can't hack it in the big city? Gonna move to the bay area now, pretend that that was your dream the whole time? Have fun always carrying a light sweater.

Jenna

I wanna roll my eyes right now, but the doctor said if I keep doing it my ocular muscles might spasm and eject my eyeballs.

Liz