I'm guessing Jennifer Aniston for #3. She's an A-list celeb, but really just a B-list movie actress. According to imdb, she hasn't done anything since "The Break-up" except for an episode of Dirt. She's got three projects "announced" but one of them is just listed as rumoured so she probably doesn't have much money coming in. Also, she doesn't have kids with Pitt so she probably doesn't get much in the way of alimony or anything.
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