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

Liz: What made you think I was gay?
Jack: Your shoes.
Liz: Well, I'm straight.
Jack: Those shoes are definitely bi-curious.

I could hardly drink my morning shower scotch.

Jack