Here's the gif to accompany #8. Different oversized sweater, but from the same season 3 episode as the pic in the lower right above. There are some pretty funny scenes in this episode, too. In the gif, Maya is working on a crossword puzzle and Finch says he's pretty good at them. Maya asks, What's a 6-letter word for... or 7-letter word for...etc., and he keeps saying, "No idea." Then Elliott says, "8-letter word for breasts," and Finch immediately answers, "Bazongas, balloons, knockers, hooters, honkers, high-beams..." And later in the show, when Maya asks Jack why he wants her to negotiate for office space with a certain guy, Jack hesitates to tell her and carefully says, "Well, because you've got that certain, you know..." and Finch jumps in, "Big hooters!"
Not a lot of action in this gif, just LSG swinging them up. CLICK