What Pennywise does to Adrian and his boyfriend is horrific. But then he turns it into a chance to throw himself a big "Welcome Back, Pennywise" party with music and dozens of red baloons everywhere.
A quick one: when Ben is first introduced, he is shown as this handsome and successful architect giving advice via video-call. As soon as Mike calls, the scene cuts to Ben in his home, and we see that he has been barefoot and wearing casual denim shorts this entire time.
When we first see adult Eddie, he's busy driving and answering a phone call from his wife, Myra. He gets exasperated by her insistence that he's doing something risky before he hangs up the phone - stating him talking while driving is a risk on its own. His wife calls him back, irritated that he didn't say his customary "I Love You", except Eddie was distracted by a call from Derry, causing him to blurt out "I love you, mommy," to a baffled Myra.
And sure enough, he crashes his car the second he gets Mike's phone call.
Richie comments on Ben's weight loss by saying they should bring up "the elephant NOT in the room!"
Richie making fun of Eddie's marriage and wife. Re-watch it a second time with the knowledge that Richie had been in love with Eddie his entire life, and all you'll see is a guy childishly trying to get his crush's attention.
Eddie asks if Richie ever married, and Richie answers yes, he's married... to Eddie's mom.
To further the joke, he says the following quote:
Richie: She's very sweet. Sometimes she'll put her arm around me, and she'll whisper to me, she'll go... [does his Jabba the Hutt impression]
Eddie: We all get it. My mom was a great big fat person. [Beverly chokes on her food while trying not to laugh anymore, while the other boys are visibly losing it] Eddie:[sarcastically] Hilarious. Hysterical.
Again, Richie taking the piss out of Eddie's job.
Beverly: Please tell me you ended up becoming a doctor, Eds. Eddie: No, I ended up becoming a risk analyst. Richie: Oh, that sounds really interesting. What does that entail? Eddie: Yeah, so I work for a big insurance firm and— [is distracted by Richie pretending to fall asleep] Eddie: Fuck you, dude. Fuck you. Richie: Was this job invented before fun? Eddie: Oh, that's so not funny. Richie: It is funny. [Eddie catches Ben laughing quietly at their Snark-to-Snark Combat] Eddie: What the fuck are you laughing at??
Honestly, this entire scene is comedy gold. You can almost see the smoke coming out of Eddie's ears.
It's mostly drowned out by the soundtrack, but Eddie can be faintly heard saying, "Let's take off our shirts and kiss!" while arm-wrestling Richie. This is never explained or commented on.
The fortune cookie scene: Pennywise conjures up illusions of creepy crawlies and eldritch abominations to the horror of the Losers. Mike reacts by smashing the creatures with the chair, screaming "It isn't real!"... until the waitress arrives and only sees a man losing it to a table.
This is made even funnier when you take into consideration that three of them are famous and one of them is the town librarian. So this poor waitress is watching the town's librarian Mike Hanlon, fashion designer Beverly Marsh, writer Bill Denborough, and comedian Richie Tozier... freaking out over nothing.
Richie:[to the waitress] Yeah, could we get the check? [awkward smile]
Richie imitating Pennywise's dance from when he was trying to scare Beverly in the first movie.
When the Losers leave the restaurant, what appears to be a Creepy Child appears and tells Richie that "the fun is just beginning." Richie gets in the boy's face and gives him a vicious, foul-mouthed death threat, only for the boy to reveal that he's just a fan quoting a line from Richie's routine, and is later revealed to be Dean when Bill encounters him again. The fact that the child was Wise Beyond His Years to develop mature Nerves of Steel in response to Richie's threat rather than being sent crying for his parents as an expected reaction from any kid being chewed out like that helps with the moment's Cringe Comedy. However, it later turns into both Nightmare Fuel and a Tear Jerker when Dean is later killed in the carnival funhouse in front of Bill, which also permanently denies Richie the chance to formally reconcile with Dean.
Richie:Are those your parents? Dean: Yeah. Richie:You want a picture? Dean:I think I'm good. Ben: Jesus, Richie. You don't remember a line from your own show? Richie: I don't write my own material. Eddie: *triumphant* I fucking knew it! I fucking knew it!
Pennywise appearing with dozens of red balloons in his hand singing about knowing Richie's dirty little secret. note him being gay
Huge YMMV on this one. Definitely Nightmare Fuel for any LGBT audience members.
Before this, Pennywise jokingly says he and Richie should play a game—maybe Street Fighter.
There's also a Funny Background Event where everyone in the park sways left and right as Pennywise sings his song.
And at the very end, Richie is closing his eyes, telling himself that none of it is real before opening them... just in time to see Pennywise dashing up to him cackling with a huge, goofy grin on its face. He's not distorting his face or shapeshifting, he's not baring his fangs, he basically just runs up and goes "Booga-booga-booga!" And the most ridiculous part is that this is what makes Richie, a grown-ass adult, scream in terror and book it out of there!
Pennywise whining like a pouty child as Richie runs off is both creepy and silly as is typical for Pennywise.
Ben tries to hide from Pennywise by getting into a locker only for Pennywise to manifest within it (making an exaggerated shocked face) and shout "Kiss me, fat boy!"
Pennywise proceeds to taunt Ben, yelling "nobody wants to kiss the fat boy... kiss me, like it's your last time!" With Pennywise's odd voice, and how he almost sings "faaaaaattt boy," you can't help but laugh.
The awkward pause between Beverly and Mrs. Kersh during a conversation they were having. She stares without blinking for a very long time.
After Richie kills Henry:
Richie: That was long overdue! Get it? Because we're in a library... [Beat] Nope. [and then he pukes]
This quick exchange after the other Losers enter the library and are shocked by Henry's dead body:
Ben: Are you all right? Richie:: No, I'm not all right! I just fuckingkilled a man! Ben: ...I meant Mike.
Eddie's near Major Injury Underreaction when Henry stabs him in the cheek. The two laugh nervously as Eddie backs up into the tub and pulls the shower curtain closed, as if to shield himself. Henry stalks forward bemusedly, only to get stabbed in the chest. As Henry stares in shock, Eddie (slinking away slowly) drops the following line:
Eddie: You should cut that fucking mullet. It's been, like, thirty years, man.
To top it off, after the Losers find Eddie bleeding through the cheek, Bev tries to stop it by trying to pinch it shut.
Another Eddie moment: Pennywise tries to attack Eddie in the pharmacy basement, putting on the Leper man from the first movie. Eddie, using his anger and strength, manages to choke Pennywise and nearly kills him. So what does Pennywise do? He vomits all over Eddie to the tune of "Angel of the Morning."
A scene later, Eddie is running frantically and slams into the pharmacy door. We see him trying to pull it open in a jibbering panic without success before Greta (now older) notes that the door needs to be 'pushed.' Eddie gives a casual "Thanks", smiles, and simply walks out.
Bill riding on Silver... forgetting that it has been put on display for years and is basically rusting away. So him trying to cycle around the neighborhood goes about as well as you expected.
The whole 'your ending sucked' gag with regards to Bill unable to write a satisfying ending in his stories. Even Stephen King himself thinks so! This running joke gets even better when you know of King's self-admitted issues with endings. Self-Deprecation indeed!
A few minutes before the aforementioned scene, Bill and Beverly are terrorized by Pennywise in the form of a skateboard thudding heavily down the stairs. When Bill flips it onto its side with the coat stand, blood begins to drip upwards, leading to the following exchange:
Of course, the levity of the situation disappears when they see the message written on the bottom of the skateboard ("CAN'T SAVE HIM EITHER"), a clear jab at Bill failing to save Georgie before and how he will fail to save Dean before the exact same thing happens to him.
Stanley standing up to himself and go off-script during his Bar Mitzvah? Awesome. Richie making a standing ovation and then being dragged down by her mother to stop the clapping and sit back down after that? Funny.
During a flashback in the Losers' hideout, we find out that Stanley's token was basically a shower cap. We see young Richie asking why Stanley brought that of all things and is told that it was to keep the spiders out of their hair. Richie starts mocking the very idea, only to turn around and find that everyone has already put theirs on.
Richie:[in a completely deadpan tone before turning back to his comic] I stand corrected.
Beverly:[giggles] Well, that's a first.
Back in the present, after exiting the clubhouse, Richie is the only one frantically scratching his hair for spiders.
Another funny gem is when the Losers go back into the Neibolt Street well house.
Richie: Well, I love what he's done with the place.
Beverly: Beep-beep, Richie.
While fighting IT in the form of Stan's head with spider legs, they lose sight of IT for a moment until Richie sees drool dripping from the ceiling and looks up.
And just before “Stanley”’s head sprouts legs, he asks Richie what’s happening to him, and Richie makes an expression that just SCREAMS, “I don’t fucking know, man.”
In a Call-Back to the first film, as the adult Losers head deeper into Pennywise's sewer lair, Eddie can once again be seen grimacing and murmuring "Ugh, grey water!" under his breath in an extremely disgusted tone. The poor dude is just so done with splashing around in dirty water.
To get to the deepest part of the lair means wading through chest-high sewage water. While the others simply get it over with, there's a shot of Eddie avoiding the floating pieces of sewage in an extremely comical manner.
As everyone burns their tokens, they bicker over how some of them will take a very long time to burn (e.g. Richie's arcade token; Eddie's inhaler). Then Mike's turns out to be the rock that Beverly threw at Henry, which Eddie points out will never burn. The others shushing him and Richie like they're still little kids just seals the deal.
Richie's reaction when Mike explains to the Losers that they are about to witness IT's true form.
Richie: I hope it's a Pomeranian.
When Pennywise first appears in the climax, he taunts Mike about "the poor Shokopiwah-yum-yum-yum". This isn't a Verbal Tic, he's reminiscing about how good they tasted!
Richie: Damn it! Eddie: Uh, all right! Not Scary At All! Richie:[grabs Eddie] No, no, no! NO. They, are, uh, they're flipped! He's fucking with us! [opens the Very Scary Door to find a closet] Betty Ripsom: [voice]Where's my shoe? [Richie turns on the light and out comes the rest of Betty Ripsom's torso] Richie:[freaking out]BETTY RIPSOM! Eddie:[yelling at Richie]YOU TOLD ME TO TRUST YOU!
Richie: [beat after screaming] He's not fucking with us! Let's get the Not Scary At All! [They open the door, only to see a Pomeranian waiting for them. They aren't convinced] Richie: Shit. Eddie: No way am I falling for this shit again. Richie: Oh, yeah, that thing's a fucking monster. [to the dog] I know your moves, you little bitch. [They turn to find that Pennywise had left them] Richie:[to the dog] SIT. [the dog complies] Richie: He did it! Eddie: Aw, that's cute. That's a good boy. [baby voice] That's a good boy, a good boy. [the dog then transforms into an Animalistic Abomination as the two scream] Eddie: SHIT! Next time, we just go with regular Scary! Richie:Next time?!
While having Ben at his mercy in an illusion of the Losers's Clubhouse that he has turned into a deathtrap, part of Pennywise's "Reason Why You Suck" Speech is the number of sit-ups Ben did to lose his baby fat.
Young Henry, pushing against the door of Bev's bathroom stall, shouts "Here's Johnny!". A film where Stephen King himself has a cameo doing such a blatant reference to an adaptation of his work that he famously hated is a beautiful piece of Refuge in Audacity.
Eddie's last words to Richie? "I fucked your mom."
Richie calling Pennywise a "sloppy bitch" in the climax and Pennywise's utter look of "Really, man?" before he turns his Deadlights on Richie.
What makes it all the funnier is it connects to a moment in the first movie where Richie calls the Neibolt place a "crackhead house", driving Pennywise to turn around to glare at him. Do not insult Pennywise's interior decorating skills.
Pennywise's various forms all share one thing: incredibly goofy walks. Whether it's an overly stiff march or one with flailing arms, he walks like an alien wearing an ill-fitting human suit (which is exactly what he is).
We see Ms. Kersh in the distant dark of a hallway staring at Beverly. Terrifying. Then Ms. Kersh walks away while flailing her arms like an inflatable tubeman.
Just Richie's entire speech to a terrified Eddie during the final confrontation:
Richie: Who killed a psychotic clown before he was fourteen? Eddie: Me. Richie: Who stabbed Bowers with a knife he pulled out of his own face? Eddie: Also me. Richie: Who married a woman ten times his own body mass? [Beat] Eddie: ...Me.
Bill's Failed Attempt at Drama in front of the Niebolt House when he says Richie said it best last time they were there. Richie initially confuses which line he's talking about.
Richie: You're lucky we're not measuring dicks? [Beverly and Ben look at Richie, their expressions screaming "Really, Richie?"] Bill: No.
Pennywise's defeat is just dripping with Hypocritical Humor. Here is a monster who has been personally tormenting the Losers Club about their deepest insecurities and fears for two entire movies, and yet It can't withstand even two minutes of being called a clown (a form It chooses to take, remember). Many fans have joked that the scene is essentially It being bullied to death.
Pennywise's last words are a final mockery of the Losers at face value... but they can also be seen as an Incredibly Lame Pun over his own now minuscule stature:
Pennywise: Look at you... you're all... grown up![Evil Laugh]
Meta
During filming, Bill Hader approached Bill Skarsgård (who was in full Pennywise costume and make-up at the time) and asked how they achieved the effect of Pennywise's eyes moving in different directions. Only it's not an effect; Skarsgard can actually do that. His response? "Oh, you mean this?" Hader's reaction is priceless.◊
The adult cast ironically appear more childish than their younger counterparts thanks to Bill Hader's tendency to make jokes during group interview. This interview shows how how Andy Muschietti the director looks so done with the cast.
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