5. “Eternal Moonshine of the Simpson Mind” (Season 19, Episode 9)
While the golden era ofThe Simpsonsis very much in the past, episodes like this one from 2007’s season prove that the show can still knock it out of the park when it tries to.
After a panicked Homer thinks he may have hit Marge during a bender, he attempts to piece his memory back together. He deduces that Marge is cheating on him, which brings him to such a low that he attempts suicide by jumping off a bridge.
Related:A character analysis of Homer Simpson
As he falls, his life flashes before his eyes in the form of one of those take-a-picture-every-day-for-X-years memes and we get a minute-long glimpse into Homer’s entire life: his mum leaving his dad, his struggles with weight, his struggles throughout puberty, his struggles with alcoholism, and a rewind across his many, many jobs.
In an episode that deals almost entirely with memory, the scene ties the whole story together nicely. It also serves as a reminder that, for all its wackiness,The Simpsonsis heartfelt and tender enough to make us care about these characters who we’ve grown to love.
4. “Hurricane Neddy” (Season 8, Episode 8)
Considering what poor Ned Flanders would later get put through, this particular scene from 1996’s season might seem small beans—but it’s the earliest example of him being put through the emotional wringer.
When the Flanders' house is destroyed by a hurricane, Springfield’s residents leap into action to rebuild it… only for it to collapse again due to their ineptitude.
This triggers an outburst of biblical proportions out of Ned, who proceeds to berate the townsfolk before checking himself into a mental institution. It’s genuinely tragic to witness a character, who’s invested their entire life in something, lose it all in one instant.
The scene where Flanders questions his faith really highlights that this is someone who has done everything asked of him, and for what? I’m sure we can all relate, as we’ve all been in similar circumstances at different points in our lives.
We may not have exploded violently at our loved ones, but who among us can honestly say we’ve never thought about it?
3. “Homer’s Phobia” (Season 8, Episode 15)
This episode from 1997 revolves around Homer discovering that a new friend of the family is gay, along with his struggles to accept that friend’s sexuality and how he believes it will affect Bart.
That Homer essentially treats homosexuality like an infectious disease reveals an unbeforeseen darkness to the character.
Prior to this episode, Homer has always been a dim-witted but otherwise lovable guy. Here, he’s cast in a more unflattering light—one that’s realistic and depressingly common. Homer is, after all, an embodiment of blue-collar Americans.
In one particularly tense scene, Homer tells the gay friend to stay away from his family, and John gives that sigh of someone who’s had to weather this intolerance many times before.
In the end, John literally has to save Homer’s life to prove his worth, and Lisa admits that this is “the most tolerant Dad gets.” That may be as funny as it is depressing, and that’s whatThe Simpsonsdoes best.
Related:The best 90s cartoons still worth watching
2. “And Maggie Makes Three” (Season 6, Episode 13)
This 1995 episode ofThe Simpsonshas, for me, aged like fine wine. I remember thinking it was just a cute bit when I first saw it. But I forgot about it for many years, then watched it again more recently—this time, through the viewpoint of a parent.
The episode perfectly conveys how, try as you might, you can’t always be there for your kids and their special moments. I’ve missed countless amazing firsts because of work, illness, or dumb luck.
The scene is also special as it’s the only one on this list that’s only witnessed by the audience, so there’s an element of us being let in on a secret, which feels a bit like a reward in some respects.
Related:The best cartoon TV characters
1. “Bart Gets An F” (Season 2, Episode 1)
Early in the running ofThe Simpsons—in fact, way back in 1990 during the show’s second season—the show delivered a real sucker punch with this memorable episode.
The stakes are laid out at the start of the episode—Bart is at risk of repeating the fourth grade—but with this beingThe Simpsons, we never consider it a threat and assume all will go well.
Related:The best and worst Simpsons characters
For most of the episode, everything plays out using various tropes relating to “studying for the big test.” Then, it swerves into emotional territory: Bart discovers he’s failed the test and will actually be held back a year. We don’t expect it, but he breaks down in tears.
And we, the audience, share Mrs. Krabappel’s surprised reaction because moments of vulnerability from Bart are few and far between. This is the first time we’ve seen him like this.
It’s truly heart-breaking to hear Bart say how he genuinely gave it his all, and it’s a sobering reminder that even giving something our all isn’t good enough at times. From the beginning,The Simpsonshas never been a show that shies away from telling the truth like it is.
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