Yes, Dear/YMMV


 * Hilarious in Hindsight: Greg tells Jimmy to stop thinking about sex, to which Jimmy says "That's like Tiger Woods not thinking about sex." Now fast forward to 2010.
 * In one episode, Jimmy unintentionally tells Kevin Smith that his latest film (a WW 2 comedy) sucks, at first Smith gets offended and demands an apology, but then he later admits to Jimmy that his film really does suck and he ends getting more funding to do a different film. A very similar scenario ended up happening with Smith in real life, after Smith directed Cop Out, Smith was pissed at critics for the negative reviews, then he lateradmitted the film really wasn't very good, and that was a big part of his decision to make Red State.
 * A movie Jimmy pitches to Savitsky (A sci-fi movie about clones used as organ donors) sounds a lot like The Island.
 * Ho Yay: Greg and Jimmy, sometimes pretending to be a married couple.
 * Squick: During the episode Speed Dating, Billy asks Jimmy to go on speed dating with him for moral support, a proposition that Christine refuses to approve of -- that is, until Jimmy tells her that Billy spends many dateless nights fantasizing himself with her, a revelation that prompts Christine to change her mind at once.
 * The Woobie: Greg, certainly during his childhood years.
 * Even more so with Sammy.