IT: 10 Saddest Moments, Ranked

IT Pennywise With Balloon

With less than two weeks until It: Chapter Two is released on Digital HD from Amazon Video and iTunes, what better way to prepare than reviewing the saddest moments from both It: Chapter One and It: Chapter Two? Every adaptation of It, as well as the source material, is known for being terrifying and, frankly, chaotic, much like the rest of Stephen King’s work.

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However, director Andy Muschietti dove deeper into the characters and the stories of It and pulled out some truly heartbreaking moments. Who would’ve thought that movies with a killer alien clown as the main antagonist would be such tearjerkers?

10 The Losers Club, Divided

After the fight against Pennywise the Dancing Clown in Neibolt House in It: Chapter One, the Losers Club brings Eddie Kaspbrak back home with a broken arm, and his mother scolds them all. She calls them monsters, tells them they’ll never see Eddie again; at this point, Richie Tozier snaps at Bill Denbrough, telling him they can’t keep trying to fight Pennywise. Richie points out that Eddie nearly got killed and getting the rest of them killed won’t bring him back. Bill’s not in the right place to hear that, and he punches Richie, who leaves, dividing the Losers Club in half.

9 Beverly in the Bathroom

Sophia Lillis Nancy Drew

It: Chapter One delivers on the scares and the sadness, and no scene is a better combination of the two than Beverly’s sequence in the bathroom. This could be referring to multiple scenes: her father attacking her after finding the poem Ben wrote her (“Your hair is winter fire,” remember?), or when Gretta Keene bullies her, but we’re talking about the bathroom scene. Yes, that one — the one where the blood erupts out of Beverly’s sink and coats the room. This isn’t the sad part, though; the sad part comes when Beverly’s dad comes in to check on her and finds her trembling on the floor and Beverly realizes just how alone she is.

8 Bowers vs. Ben on the Bridge

IT 2017

When the audience is first introduced to Losers Club member Ben Hanscom (Jeremy Ray Taylor and Jay Ryan), they learn he’s the new kid (“the new kid on the block,” as Beverly playfully points out). This, along with his physical appearance, makes him a prime target for bullies in Derry, especially the infamous Henry Bowers. When Bowers and his gang attack Ben on the Kissing Bridge in Derry, carving an H into Ben’s stomach before he manages to get away and run to the Losers, it’s one of the saddest moments in the entire series. People driving by turn a blind eye to poor Ben, isolating him and giving him a bone-deep, lonely fear.

7 The Death of Adrian Mellon

IT Chapter Two Adrian Mellon Scene

Diving from It: Chapter One into the deep end of It: Chapter Two, we find one of the saddest moments in the entire series. While the attack on Don Hagarty and Adrian Mellon opens Stephen King’s original novel, It, the scene doesn’t appear in the movies until It: Chapter Two. Adrian and Don are attacked viciously in the street to open the sequel to the 2017 fan favorite It: Chapter One. The two are shown being beaten before Adrian is tossed over the bridge. By the time Don gets down to the water, he sees that Pennywise has Adrian, and he eats his heart. This devastating scene only goes from bad to worse, and nobody will soon forget Don’s response to losing the love of his life.

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6 Richie Tozier Faces His Demons

Bill Hader as Richie and Pennywise in IT Chapter 2

Though this scene is in It: Chapter Two, it actually takes place back in 1989, when It: Chapter One takes place. This scene is a flashback for Richie Tozier (Bill Hader) while he’s trying to find his token. Each member of the Losers Club needs to find their token, something to symbolize their past, and Richie returns to the theater arcade where he once played Street Fighter, after his aforementioned fight with Bill. The audience is shown young Richie (played again by Finn Wolfhard) as he plays the arcade game with another boy before Henry Bowers arrives and starts hurling homophobic slurs at Richie. The other kids call Richie “Trashmouth,” because he’s always quick with a cutting joke or devastating one-liner, but, this time, he’s silent as he stumbles backward out of the arcade and flees. After this, he carves R+E into the Kissing Bridge, then gets attacked by Pennywise and a statue of Paul Bunyan, so Richie just has a deeply saddening day overall.

5 January Embers

IT Chapter Two Ben Poem

Beverly Marsh, played by Sophia Lillis in It: Chapter One and Jessica Chastain in It: Chapter Two, has a terrible life from the get-go. Her dynamic with her father is enough to bring tears to anyone’s eyes, but the scene when her father finds out about the poem Ben Hanscom wrote for her (“Your hair is winter fire. January embers. My heart burns there, too.”) is next-level upsetting. He sniffs her hair, tries to assault her, and Beverly has to resort to smashing him on the head with the toilet seat lid. In It: Chapter Two, there’s another flashback to Beverly and her father where he sprays her with her mother’s perfume and then holds her. Every moment between Beverly and her dad is deeply, deeply saddening.

4 The S.S. Georgie

We’ve already looked at the opening sequence in It: Chapter Two when we discussed the death of Adrian Mellon, but an even sadder moment opens the entire series when Georgie dies at the beginning of It: Chapter One. Bill Denbrough (Jaeden Lieberher) makes a little paper boat for his little brother, Georgie (Jackson Robert Scott), to sail in the rainstorm outside. Bill doesn’t go with him, a decision he’ll regret for decades to come, and Georgie is lured into the sewer by Pennywise. Pennywise takes a bite out of Georgie’s arm, and baby Georgie tries to crawl away, screaming his brother’s name as he’s pulled into the drain, never to be seen again — except, of course, by Bill, who is tormented with Georgie’s ghost by Pennywise many times afterward.

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3 We Have to Get Him out of Here, Bev

Eddie and Richie IT Chapter One

Not every member of the Losers Club survives until the end of It: Chapter Two. In fact, we lose two members of the Losers Club before the story's end, and one of those members is Eddie Kaspbrak, played by Jack Dylan Grazer and James Ransone. Eddie struggles with being brave and almost lets Richie die at one point in It: Chapter Two. This only pushes him to be better, to remember that Pennywise can be defeated, making him the crux of the whole thing: he tells the Losers they can kill Pennywise because he was able to hit him. Eddie knows they can kill monsters if they believe they can, and so, when Richie is caught in the Deadlights, Eddie is the one who saves his life. Tragically, as he and Richie are reunited, Pennywise spears Eddie through the chest, mortally wounding him. Richie tries to save Eddie, but the other Losers force Richie to leave Eddie’s corpse behind once they realize he’s already gone. They know Richie would sooner die than leave Eddie, and so they drag him out of Neibolt House. The scene ends with Richie being restrained in the street while screaming and sobbing; even though Pennywise is finally, finally gone, for the Losers, it’s a hollow victory.

2 Guess Stanley Could Not Cut It

Every fan of It dreads the inevitable: losing Stanley Uris. Stan, played by Wyatt Oleff as a child and Andy Bean as an adult. Stan’s first appearance in the novel It in a section entitled “Stanley Uris Takes A Bath,” and it’s not a happy sequence. It’s one of the saddest moments in the entire series, and Andy Bean delivers on the moment that Stan takes his own life in It: Chapter Two. Stan believes he isn’t brave enough to return to Derry and fight Pennywise again, so he removes himself from the equation entirely. Stan says, “I did it because I was afraid to come back. If we weren’t together, then we would all die. So, I took the logical step. I removed myself from the board.” Pennywise taunts the other Losers with this knowledge, sending them a message in parts that reads: “Guess Stanley Could Not Cut It.” Finding out from Stan’s widow, Patty, that Stan had passed away is devastating to the Losers; Stan is the first of the Losers to die, and his loss is a physical pain to his best friends.

1 Dear Losers, When You Read This…

The saddest moment in both It movies is the final sequence of It: Chapter Two, where we see the ends to the characters’ stories. It’s not the ending that’s sad, though; it’s Stan’s voiceover, as he reads the letter he wrote to the Losers before he took his own life. In that letter, he says: “I’ve lived my whole life with fear. I was scared of what would happen. I was afraid of what I left behind. Don’t do it. Be who you want to be. And be proud of it. And when you find someone who loves you, never let them go.” This is devastating in and of itself, especially “Be who you want to be. Be proud.” over Richie Tozier, but the saddest part of all comes at the very end. Stan ends the letter with the Losers, all seven of them together, and they say: “Take this letter as a promise. A promise I ask you to make to me. Each other. An oath. They know, when you’re a Loser, you have nothing to lose anymore, so. Be honest. Be brave. Fight. Believe. And never forget: We are Losers, and we always will be.” To end such a deeply emotional and impactful story on this note is enough to bring anyone to tears, and many ended the movie crying as the credits rolled.

NEXT: The 10 Funniest Moments From It Chapter 2

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