It's hard to choose the ten BEST Simpsons episodes, so this list focuses on a variety that encapsulates all the show does so well.
  1. Marge v The Monorail (Season 4)
    An obvious choice, but it's obvious for a good reason. It's one of the more absurd episodes from the earlier seasons. Phil Hartman does a great guest spot as Lyle Lanley and performs "The Monorail Song" which is one of the best Simpsons songs. Plus, it's impossible to not laugh at the line "do you wanna change your name to Homer Jr? The kids can call you Hoju!"
  2. Homer v The Eighteenth Amendment (Season 8)
    This might actually be my favorite episode, or at least the funniest one, in my opinion. As if Homer becoming The Beer Baron wasn't good enough, there's that perfect old-timey narration throughout. This episode is basically all jokes, so it's perfect.
  3. You Only Move Twice (Season 8)
    Homer getting a job with a company run by a boss who turns out to be a super villain is already funny, but make that boss voiced by Albert Brooks and you have comedy gold. Brooks improvised a lot of the great lines he has in this. I don't even need to talk about this one, you should just watch it.
  4. Lisa The Greek (Season 3)
    These next few are all on the list because they're very sweet episodes. This one is a great episode dealing with the relationship between Homer and Lisa. She helps him bet on football games and is always right so they form a bond. Once she realizes that that's the only reason he's been so close to her, she's hurt. Homer redeems himself at the end and all is well. Also, Ralph's best day of his life was finding out he didn't have worms anymore.
  5. The Way We Was (Season 2)
    I think this is the first (of VERY many) episodes to recount how Homer and Marge met and fell in love and it's the introduction of "Close To You" by The Carpenters being their song, which plays even in The Simpsons Movie. This was also one of the few credited to Sam Simon, which, to me, makes it extra special.
  6. Grade School Confidential (Season 8)
    This focuses on the relationship between Principal Skinner and Ms. Krabappel. They're both such messes of characters that feel so human in this episode, which makes you so happy to see them making each other so happy. This one is a perfect mixture of humor and emotion. Homer's reaction to the gossip that they had sex in the school: "I thought her name was Crandall!"
  7. Homer's Enemy (Season 8)
    The premise is essentially "how would a real world person deal with Homer's antics?" The outlook is grim, but hilarious. This is a divisive episode because many think it makes Homer seem just like a jerk instead of an idiot. I think instead what it does is show how deranged every character in Springfield actually is; it's not just that Homer's an idiot, it's that the townspeople put up with a lot of it and cheer him on.
  8. 22 Short Films About Springfield (Season 7)
    This is a great, somewhat-experimental, episode that focuses on little stories all about the different side characters of Springfield, that is also a Pulp Fiction parody at the same time. My favorite segment is the one with Skinner cooking dinner for Superintendent Chalmers, but they're really all pretty great. Definitely worth watching for the structure alone.
  9. Cape Feare (Season 5)
    Sideshow Bob sings the score to H.M.S. Pinafore and also has the rake gag. There really isn't anything left that needs to be said, except "bake him away, toys."
  10. Homer the Heretic (Season 4)
    This one is special to me because it's the first one I watched that kicked off getting back into the show later in life and really appreciating everything about it. It's also just a great argument against religion that isn't annoying and preachy.