The Simpsons: Milhouse’s Best Moments Across 35 Years, Ranked

The Simpsons officially turns 35 later this year, and one of the major stars behind it all is leaving the series very soon. Pamela Hayden has announced that with the next episode of The Simpsons Season 36, the star will be retiring from the series. Hayden has brought to life multiple characters over the course of the series’ run, but will be best remembered for her time as Milhouse. Bart’s best friend has been the source of many hilarious moments over the years, so there’s no better time than ever to celebrate some of the best moments we’ve ever gotten for the character.

The Simpsons currently has 36 seasons and 774 episodes under its belt as of Pamela Hayden’s retirement from the series, and that’s a lot of Milhouse to sift through for the best. Naturally this list won’t have ever major moment from the series across the years, and might favor a certain era over others (with good reason), but hopefully is a fun way to celebrate Hayden’s impact as the little nerd who’s taken so much abuse on the chin only to keep going. Everything really is coming up Milhouse.

10. “Is it because of my small calves? They’re the hardest place to add mass!” – Future-Drama / Season 16, Episode 15

“Future-Drama” might not be considered part of the overall canon for The Simpsons, but this glimpse into Bart and Lisa’s future lives has a ton of great Milhouse. In this version of the future, Milhouse has become obsessed with working out and building muscle. He’d even dated Lisa for a while after saving her from a burning building (a fire that he started), and Hayden’s buffed up version of the character is packed with hilarity. Especially when he drops the very memorable line after getting dumped by Lisa, “Why did Lisa dump me? Is it because of my small calves? They’re the hardest place to add mass!” The scene even ends with a better line, “Time to strike when the iron is sad!” Perfection all around.

9. “Which kind of sprinkler do you like?” – Summer of 4 Ft. 2 / Season 7, Episode 25

“Summer of 4 Ft. 2” is basically nothing but banger after banger for Milhouse. While the episode itself arguably has some of the more memorable moments involving Milhouse, (“You got the dud!”), this kicks off the episode with just childish delight that only Milhouse has. It not only sees him recreating all of the sprinklers he’s a fan of, but also has him assuming that Bart knows them too. But then the kicker comes soon after when he bursts out the class with “Up yours, Krabappel!” This is only the start of the episode, and it’s the start to one of the best episodes of the entire series.

8. “Why did I have the bowl Bart? Why did I have the bowl?” – The Canine Mutiny / Season 8, Episode 20

Some of the best Milhouse moments are when he challenges Bart or the two are an actual equal footing, and one of the best comes out of nowhere. He knows Bart was lying to him about Santa’s Little Helper eating his pet goldfish, and challenges it with “Why did I have the bowl?” It’s both the repetition of the line itself along with Hayden’s energy. It’s the kind of energy you can only assume is someone who had been debating it in their head for a long time, and is tired of Bart not relenting. It’s quite a fun moment for Milhouse where he gets tired of the status quo yet has no power to change this. Quite the encapsulation for Milhouse overall.

7. “But my mom says I’m cool” – Burn’s Heir / Season 5, Episode 18

“But my mom says I’m cool” is one of those lines that has broken through The Simpsons to enter the general lexicon. It all comes from the smallest, but most impactful Milhouse scene on this list thus far. Not only does he immediately seem as lovably pathetic as fans love with “I have nothing to offer you but my love” but then it’s followed up with the iconic line that only makes Milhouse seem even geekier than before. It’s definitely a moment where he’s kicked while he’s down, but it’s all in good fun because that’s just who Milhouse is. And we love him.

6. Milhouse the fugitive – Lisa’s Rival / Season 6, Episode 2

Rather than being a standout line, this sequence of events is memorable for a different reasons. The Simpsons often has plenty of running gags on the sides of any given episode, but this Milhouse side plot was truly special. It began with the joke of Bart revealing that he’s put Milhouse on America’s Most Wanted list, and then kept on building until it went into a full parody of The Fugitive. Putting Milhouse in Harrison Ford’s place, he’s being held at gunpoint by a Tommy Lee Jones lookalike who even says a famous line from the movie, “I don’t care!” All capping off with the faint, “My glasses!” Just perfect Milhouse.

5. Thrillhouse – Marge Be Not Proud / Season 7, Episode 11

Just like earlier in the list, this one is a very small moment but packs such a punch. It’s not one of the gags that’s broken into general language like the other, but Thrillhouse hits so much harder thanks to that visual gag to cap off the joke. As Milhouse plays the sought after Bonestorm game that Bart steals in the episode, he’s having so much fun from just entering his name that cuts off at “Thrillho.” Which in turn, has the same number of letters as Milhouse, so his regular name wouldn’t have cut off so hilariously. But does Thrillhouse care? Nope, he’s having too much fun.

4. “We already did it. It took seven hours but we did it. It’s done” – Radioactive Man / Season 7, Episode 2

Speaking of times where Milhouse gets to do things Bart is unable to, “Radioactive Man” is likely the best example as Milhouse gets the role as Radioactive Man’s sidekick, Fallout Boy, in the Radioactive Man movie. There were a few big moments for Milhouse in the episode, but the best is undoubtedly when he expresses his frustration at doing the “Jimminy Jilickers” catchphrase again. Hayden’s low selling of the frustration merits a tone that Milhouse never really takes in The Simpsons again. It’s so memorable in an episode full of Milhouse moments that it sticks out.

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3. Guess who likes you – Lisa’s Date With Density / Season 8, Episode 7

Now this? This one hurts as Milhouse is at the bad end of Nelson. First, there’s the bit of Lisa figuring out she has a crush on Nelson which leads to the “Nobody likes Milhouse!” line when the class is ridiculing her for it. Secondly, Milhouse gets rejected by Lisa once more only to be positive about the fact that she sees him as a big sister. He might feel bad about this result at first, but ultimately helps Lisa because he pathetically believes she’ll respect him if she sees he’ll do anything for her. It’s then taken to the even more memorable level with one of Milhouse’s biggest Ls as he passes a note to Nelson with “Guess who likes you” only to then be punched so hard that his ears need to be filled with gauze. It’s Milhouse at his lowest, but it’s sure at his funniest.

2. “Is this the untimely end of Milhouse?” – Lemon of Troy / Season 6, Episode 24

“Lemon of Troy” is hands down one of the best episodes of The Simpsons overall. It’s packed tight with tons of jokes, and its cartoonish expansion of the rivalry with Shelbyville makes for one of the best stories. Especially as Bart and his friends go on an adventure to the other side. Milhouse himself has so many of these great moments of childlike wonder too with words like “squozen,” or pointing out Grandpa Simpson with “Hey everybody, an old man’s talking!”

Then there’s the scene of his grabbing the camouflage clothes and having the fantasy of being able to hide among the trees. But nothing is better than when he meets a fellow Milhouse. First the dramatic “Is this the untimely end of Milhouse?” then the sweet embrace between the two of them where Milhouse says that’s what it must be like “when doves cry.” It’s got everything you want from Milhouse packed into a tight 22 minutes.

1. “Everything’s coming up Milhouse!” – Mom and Pop Art / Season 10, Episode 19

It couldn’t be anything else. “Everything’s coming up Milhouse!” is undoubtedly the most iconic line Milhouse has ever spoken. Although it comes up much later in The Simpsons that fans might expect, and it really comes out of nowhere very late into “Mom and Pop Art” itself, it hits like a truck. It’s a perfect encapsulation of what makes Milhouse, and in turn Pamela Hayden’s time with the character so special. It’s so full of hope despite being frustrated not soon before, and shows how Milhouse really makes the most out of little victories.

It comes up later in Season 22 as he says it while riding on top of an eagle (shortly after Lisa gives him romantic interest hope again), and is likely the first thing that fans remember Milhouse for. Hayden has given The Simpsons fans millions of memorably Milhouse moments over these three and a half decades, and as she retires, fans can look back on moments like this to remember her fondly. Milhouse has lived quite a life. Everything really did come up Milhouse.