1) Pierre should be caricatured as dishevaled, messed up hair, tattered clothing, spilling his wine.
2) Jancis should be caricatured as an older Jewish woman, carrying a bottles of Manischewitz.
3) Eric was a start cadet at Space Camp, but was too tall for the astronaut program, so he became a wine critic. He should have a wine glass in his hand, which he is not spilling.
4) Growly the Bulldog should be wearing a NY Jets scarf.
5) Slightly more abstract, the final caricature is a nerdy wine bottle in oversized gasses.