The Boys: Homelander’s Most Outrageous Moments Ranked

Warning: Contains spoilers for The Boys season 3 finale & NSFW content.

The Boys is notorious for its increasingly outrageous and darkly comic moments, starting with the gruesome death of Hughie’s girlfriend Robin in the first episode, and just getting more extreme from there. Season 3 was no exception, giving us A-Train’s horribly tone-deaf attempts to cash in on his ethnicity, The Deep’s burgeoning new relationship with an octopus, and superhero-themed dildos. We even saw a recreation of what it might have looked like if Ant-Man really had just crawled up Thanos’ rear end and exploded him from the inside.

Some of the most shocking moments from The Boys’ three seasons so far, though, have come courtesy of the leader of the Seven, the mentally unstable and terrifyingly powerful Homelander. Here are his top 10 shocking moments, ranked in order of just how outrageous they are.

10. Masturbating Off the Roof

Season 2, Episode 8, ‘What I Know’

Outrageous moments in The Boys mostly come in two flavours – sexual and violent. At the end of Season 2, having suffered a series of personal defeats and humiliations, Homelander tries to cheer himself up with a little self-love – fair enough. But he chooses to do so off the roof of the Chrysler Building, while repeating to himself “I can do what I want!” over and over again. It’s a chilling bit of foreshadowing for his character arc in Season 3, wrapped up in a classic The Boys-style warping of a typical superhero scene. You’re only supposed to stand on the building and stare off into the distance, Homelander.

9. Shooting Down the Mayor’s Plane

Season 1, Episode 1, ‘The Name of the Game’

Over the course of the very first episode of The Boys, it is slowly revealed that the superheroes on this show are not nice people. By the time we reach the end of the episode, we’ve already seen A-Train’s half-hearted apology for killing Robin, and we’ve seen The Deep sexually assault Starlight. But we discover just how cold and ruthless Homelander is towards the climax, when he shoots down the Mayor of Baltimore’s plane, with the Mayor’s young son as well as several other people on board, because the Major had threatened to reveal the existence of Compound-V. At this point Homelander seemed to be mostly dancing to Stillwell’s tune, but even so, his complacency in doing something so awful was a clear sign of the horrors to come.

8. Ranting at a Bedridden Stormfront While She Pleasures Him

Season 3, Episode 1, ‘Payback’

By the first episode of Season 3, Stormfront has become bedridden due to her injuries from the Season 2 finale, and Homelander visits her, which is actually surprisingly nice of him. While he’s there, she uses her hand to pleasure him. This by itself would not necessarily be outrageous – they are continuing their sexual relationship regardless of her disabilities, which is entirely reasonable. But the way the scene is approached makes this potentially romantic scene outrageous in a similar way to the rooftop scene from the previous episode.

There’s little tenderness and a lot of business-like getting on with things as Homelander whines and complains about how hard done by he is and Stormbreaker offers to “help”, with Homelander lowering her bed and allowing her to do so while continuing to rant and rave about how no one is treating him well enough. The whole scene gets more and more uncomfortable as Stormbreaker starts to talk about her Nazi master race fantasies, and Homelander shoots those down by claiming to be a master race himself and walking out, so that no one comes out of this scene looking good at all. The sheer unpleasantness of the whole thing puts it up in The Boys’ Uncomfortable Sex Scenes Hall of Fame.

7. Throwing Ryan Off the Roof to Get Him to Fly

Season 2, Episode 3, ‘Over the Hill with the Swords of a Thousand Men’

Homelander is absolutely convinced that his son Ryan will be able to fly, just as he can. Ryan insists that he can’t fly and refuses to jump off the roof, at which point Homelander pushes the poor kid off, and he flops onto the ground and blacks out. To be fair, Homelander is entirely correct that Ryan doesn’t experience any permanent damage from this, but he didn’t know that for sure, and he doesn’t manage to get the boy to fly either. Encouraging your kids to test out their abilities is one thing – shoving them off a roof against their will is quite another!

6. Abandoning Flight 37

Season 1, Episode 4 ‘The Female of the Species’

The act that would hang over Homelander and Maeve’s heads for the next couple of seasons, Homelander abandoning the passengers on Flight 37 to die and insisting that Maeve do so too is one of his coldest actions in the show. The decision is purely and calculatingly logical. The intention had been to save the passengers, until Homelander himself accidentally kills the pilot and destroys the controls. But whereas a more heroic character could be persuaded by his red-headed female companion to save just a couple of people if he can’t save them all (literally the plot of Doctor Who’s ‘The Fires of Pompeii’), Homelander won’t take even one child with them, because he doesn’t want any witnesses to tell the world it was his fault. He then claims to the media that they got there too late because they haven’t been allowed into the military, taking advantage of the situation for his own gain. It is logical, pragmatic, and utterly heartless.

5. Forcing a Woman to Take Her Own Life

Season 3, Episode 2, ‘The Only Man in the Sky’

Homelander’s birthday episode is back-to-back outrageous moments for the character. This one is one of the grimmest. A young woman contemplating suicide has been selected as his “annual birthday save” (it’s pretty clear no one would have stepped in otherwise). When Homelander finds out that Stormfront has herself died by suicide, he takes out his grief on this poor woman and forces her to jump to her death even after she makes it clear she doesn’t really want to. It’s one of the most uncomfortable moments in the entire show, is genuinely difficult to watch, and unlike Homelander’s earlier murders, it’s motivated purely by his emotional distress, with there being no logical reason to kill this woman at all, and every reason to save her. This marks the start of Homelander’s increasingly erratic and dangerously violent behaviour throughout the season.

4. Revealing his True Self on TV

Season 3, Episode 2, ‘The Only Man in the Sky’

The same episode culminates in Homelander finally snapping and letting his true personality show on live television during his birthday show. Up to this point, Homelander has hidden his true self from the world, putting on a façade that looks a lot more like a “traditional” superhero while behaving appallingly behind closed doors. But when a heckler in the audience mocks Stormbreaker’s death, he interrupts Starlight in the middle of trying to cover for him to tell the audience what he really thinks – “I’m stronger, I’m smarter, I’m better!” Homelander has had enough of being controlled and he won’t take it anymore, and he wants the whole world to know it, as he calls out “don’t you dare stop rolling Roger!” As he tells the world “You’re not the real heroes, I’m the real hero,”, it’s shocking and outrageous and Janine’s stepfather Todd is lapping it up…

3. Getting Off On Milking a Cow and Drinking the Milk

Season 3, Episode 7, ‘Here Comes a Candle to Light You to Bed’

Back on the subject of outrageously entertaining sexual fetishes, Homelander’s obsession with breast milk reaches new heights in Season 3 as well. Homelander’s Daddy Issues are a major source of drama for the show, but his Mommy Issues – which are equally severe and deep-seated – are more often played for laughs. We’ve seen him spy on Stillwell while she was pumping breast milk in her office, we’ve seen them engage in breastfeeding-based role play, and we’ve seen him drinking her leftover breast milk with relish after murdering her, so this is a well established character trait by now.

But when Homelander finds himself wandering around a farm in some emotional distress during a political speech for Dakota Bob, he takes this obsession to a new level. Milking a cow and drinking the milk might seem like a perfectly sensible thing to do on a farm, but Homelander is clearly getting off on milking the cow and then drinking straight from the bucket, which is what makes it so outrageous. The whole thing is hilarious, with ‘Crimson and Clover’ providing the perfect soundtrack for this outrageously silly moment.

2. Forcing The Deep to Eat Timothy

Season 3, Episode 3, ‘Barbary Coast’

Several of the most memorable moments from Season 3 involve The Deep’s relationship with at least a couple of different octopi, but this one is surely the grossest (yes, even including the octopus-sex). In order to get back into the Seven, Homelander sadistically forces The Deep to eat Timothy the octopus live, even as The Deep weeps that he can hear Timothy begging for his life. It’s ridiculous and awful and squirm-inducingly hilarious all at once. The show continues to get mileage out of The Deep’s relationship with sea-creatures, while also using that to remind the audience of Homelander’s sadism and showing his increasing lack of concern for what other people think of him over the course of this season.

1. Blasting Off a Man’s Head in Front of a Crowd

Season 3, Episode 8, ‘The Instant White-Hot Wild’

It’s no coincidence that the highest ranked entries on this list are all from Season 3, as this most recent season has seen Homelander fall right off the slippery slope of sanity and behave more and more outrageously as his confidence in his own popularity no matter what he does grows. And this is the inevitable culmination of that arc.

Throwing Ryan off a roof and abandoning Flight 37 were terrible things to do, but there was also a cold, cruel logic to them. But in the final scenes of Season 3, Homelander reached terrifying new heights of cruelty – terrifying because there is no longer much logic, and no calculation, to his actions. He now feels able to lash out whenever he wants to, and murder people in broad daylight in front of a crowd, because they have upset him (granted, he was protecting Ryan, but that drink the man threw at him really wasn’t going to hurt the child Homelander himself threw off the roof once). It’s both his most outrageous moment, and his most chilling. We can’t wait to see just how more outrageous he can get in Season 4.