21. Why You Crying? (Lopez Tonight)
When it debuted: 2009
Segment lowlight: Lopez mocks Lou Pinella's retirement from the game he devoted his life to.
There is not much that didn't offend about Lopez Tonight. As you can guess, you'll be seeing more of George on this list. This lovely segment involves George watching videos of famous people crying and then mocking their tears.
Granted, reality stars and entitled celebrities crying about not making enough money or the pressures of fame doesn't exactly invite sympathy, but that doesn't mean mocking them is funny. When Lopez rags on people who have reason to cry, as Pinella did, we remember there is truly nothing funny about seeing a grown man cry...and even less funny about another grown man trying to make fun of him.