This episode of The Best of the Bad Guys focuses on Pennywise from Stephen King’s It and was written, narrated, and edited by Mike Holtz.

Sometime around the 16th century, a shape-shifting alien life-form landed here on Earth with nothing to eat except for our children. But it gets worse! It’s not just enough to eat the children, the being must scare them as much as possible first. It supposedly makes them taste better. Like when you put a lime in a Corona. Only with fear and murder. You get the idea. You wish you didn’t but you do. So, this supernatural being takes the shape of whatever scares the children the most. A spider? Their abusive fathers? The prices at Disney Land these days? Or its personal favorite, Pennywise The Dancing Clown. Because most sane people are desperately afraid of clowns.

The character was brought to life by the God of so many other disgusting, vile, and downright loathsome creatures and things that go bump in the night, Stephen Effing King! Or just Stephen King if you’re offended by cursing. Which, is weird that you’re offended by innocuous words while watching a video about an alien that likes to eat children but I’m not judging.

Today, we’re not delving deep into King’s version of IT, but rather the film and TV versions of the character. Welcome, to “The Best of the Bad Guys”, where I, Mike by the way, will be ranking the best of cinema’s worst villains on a case-by-case basis. We’ll be talking about both Tim Curry‘s and Bill Skarsgard’s versions of the character as we rank the best kill, scariest moment, quotes, and even the most frightening looks of that big-toothed piece of sh*t (bleeped): Pennywise the clown.

Get your popcorn anywhere but from the clown in the storm drain, settle in and join us as we rank all things Pennywise. Starting with….

PENNYWISE BEST LOOK

For Pennywise coolest look, you can give me all the Andy Muschietti Mama-type oogey-boogies you want to throw at me. You can give me gigantic Beetlejuice worm-looking Pennywise, the far better looking of the two Spider-Pennywise’, Bill Skarsgard big-head and way too wet lips Pennywise you want….but Pennywise has never been more frightening than good ole’ Tim Curry in some regular ass clown makeup.

There is just something about the natural, haunting look of a grown man wearing those baggy, yellow parachute pants that probably smell like Jason Voorhees post-Jason Takes Manhattan toxic waste bath dipped in the sins of OJ Simpson with the lipstick smeared into his teeth that freaks me the hell out. It’s imperfect, cheap, and off-putting in all the ways that make him so frightening.

Suddenly when this “Movie of the Week” looking psychopath breaks out his alien teeth or Mario’s himself down a pipe, it’s far more frightening than someone who doesn’t look human to begin with. It makes you feel like this child-murdering psychopath dressed in a clown suit can get to you anywhere.

Which, is a lot more upsetting than any of his other-worldly forms in a realistic-based fear type of way.

PENNYWISE Best Quote

I very, very much considered this scene a contender for Pennywise’ “Meanest Moments” but for a thing that feeds on young children….a catfish/fat shaming/sexual assault just couldn’t compare. But my lord was an unholy triumvirate of awful regardless.

In this scene, from part two of the 1990 mini-series, John Ritter’s Ben is all grown up and finally about to do tongue stuff with the woman of his dreams. For far, far too long. You feel great for the guy, even if he is kind of Mark Wahlberging her mouth a little bit. Seriously, have you ever seen Mark Wahlberg kiss? It’s like watching the worm version of Freddy Krueger in Dream Warriors trying to swallow Patricia Arquette whole.

Anyway, Ben and Bev are finally making out feverishly when he looks into the mirror American Psycho Christian Bale style. Only instead of checking his guns out, he realizes he’s got a smidge of clown makeup on his face and mouth and that Bev is wearing clown pants and gloves.

Don’t get me wrong, those pants would be horrifying on anyone not tripping balls at a Juggalo convention….but in this case, he realizes that he’s been sucking face with his biggest fear…Pennywise himself.

To make matters worse, Pennywise rears back (his makeup smudged as well, which somehow makes it feel extra gross), smiles big, and says ”Kiss me, fat boy!”

The invasiveness and awfulness of that moment being compounded with a fat joke is just extra cruel. I would have finished our make-out session and then never called him back. It’s the principal of the matter.

In all seriousness, as mean and freaky as this scene is….the fact that Tim Curry could deliver it in a way that was both funny, quotable, and still frightening is a tribute to why he’s so damn special as an actor.

PENNYWISE MEANEST MOMENT

This one is tough. Pennywise is a real dick. You could choose from him impersonating kids dead dads, using the severed head of a recently deceased friend to communicate, or him catfishing Ben into a quick make-out session. But the thing is when it comes to an alien that eats children…there’s kind of nothing meaner than that.

The obvious moment that comes to mind is either of the two Georgie scenes. Sadly, we had to watch that kid die twice. If they make another remake that poor kid is going to start getting into Uncle Ben territory. Then to have Pennywise the Dancing Douche use his form multiple times to taunt Bill….I could see how that could easily take the cake. Then there’s the moment in IT Chapter 2 when Pennywise lures the skateboard kid into the house of mirrors and makes Bill watch helplessly as Pennywise eats another child he can’t save. Pennywise was again, very Mark Wahlberg in Fear at this moment, (Wahlberg’s voice) “Let me in ya’ house so I can eat this little skateboard kid right here. And Nicole, go get me a coke. I am the eater of worlds. Hey yo, Eddie. Say Hi to your Motha for me”. Wahlberg is catching strays in this video a lot. He doesn’t deserve that. He probably does.

If we’re going for longevity here, you could say Pennywise was as mean to Bill as anyone. But as far as a single scene goes, I will give this one to the poor little girl under the bleachers in IT Chapter 2. This sweet little kid follows an ember under the bleachers because she doesn’t want to watch her brother’s stupid baseball game (probably for the fifth time that week) and runs into Pennywise. She quickly says f*ck that THERE’S A CLOWN UNDER HERE! Before Pennywise starts crying on the spot like that manipulative significant other you wish your friend would leave… and she takes the bait.

This poor little girl just wanted to have Pennywise get rid of the birthmark on her face that she gets made fun of for and instead, he eats her face off. That just makes me really sad.

Quick side note here: You could also go with one of the Derry massacres we hear about throughout the movies…but we never really saw those for the most part. Who knows, maybe the new TV Show ‘Welcome to Derry’ will go to all those places we don’t really want it to.

PENNYWISE Grossest Moment

I’d like to call this one the fortune cookie f*ckaroo (bleeped)…and we’re going with the original scene in the ABC mini-series. While the remake added some nice touches (like severed heads floating in the fish tanks all around them) when it comes to gross-out gags, I’m a practical FX over CG guy any day of the week.

In the scene, the now grown-up Loser’s Club gets together for some laughs, cocktails, and Chinese food at the restaurant from the Drake and Kendrick beef. They are having a great time until Bev opens up her fortune cookie and it explodes blood all over her face. A practical blood gag that you can tell startles the Hell out of her in real life…and us too.

Suddenly everyone’s fortune cookies start shaking at the table and turning into little monsters of different sorts. There’s a moving human eyeball, a crusty crab crawler thingy, a gigantic spider, and finally the worst of all…. an unformed baby bird with all of its goo.

WHO THE HELL THINKS OF THIS STUFF? A skinless baby bird inside of a fortune cookie? I can’t think of anything worse. Maybe in the whole world. Human Centipede didn’t even do baby birds inside of fortune cookies. And this was on Cable TV!

PENNYWISE’S BEST KILL

You know, there aren’t a ton of kills shown on screen in this franchise because it’s honestly more frightening to watch Pennywise play with his food or “salt his meats” as he says. That’s a super gross way of putting it, clown man. But surprisingly this award is going to go to Andres Muschietti’s IT Chapter 2. Which, I’ve shockingly talked about far more than I expected to today as it’s my least favorite of all four half installments. Once again, the opening sets the tone for the entire movie when a couple of homophobic douche nozzle Derry residents are beating up a gay couple outside the fair while some snot nose brat roots them on. What are these guys related to the Melaneys from Halloween Kills or something? I guess at least that storyline would have had more of a point than what you did with them huh, David Gordon Green? I bet that guy doesn’t even finish his sandwiches…anyway we’re getting off-topic.

After the puppy-kicking mouth breathers drop the guy into the river, he’s drowning and looks to the shore to see Pennywise hovering around like a cage fighter sizing up his opponent in round one the way I do the donut display case in the morning.

You see his yellow eyes in the distance and it sends chills down your spine. By the time his boyfriend has found him, Pennywise is dangling him in the air before taking a shark-like chunk out of his chest.

What makes the scene so cool though is not only the way Pennywise looks by this waterfront at night but the way he chomps on his meat after the kill. That’s some mother effin great sound work right there, guys! I think if we had more of this Pennywise, rather than jump scare Jerry throughout the film, it would have been a far more frightening film as a whole.

PENNYWISE SCARIEST MOMENT

What I want to say here is every single time Tim Curry appeared as Pennywise the Clown throughout the entirety of the 1990 film. Because to be honest, there was no one moment that stood out above all others. But with each tiny little snippet where he would show up, it was more the anticipation of what he was GOING to do that scared me so.

Showing up while a kid is forced to shower after gym and cornering him before flying down a pipe like some Old Spice commercial directed by Satan is insanely dark. Even if all he does is threaten him. Standing on the side of the road laughing as a car drives by, digging graves, and popping balloons full of blood in the library…..it was always about the lead-up for Tim Curry’s Pennywise. The movie may have never really had the budget to make good on its threats, for which I am almost thankful. I don’t think kid me could have handled it.

But alas, I refuse to cop out and not do as promised. So, while I think Tim Curry’s Pennywise is far more frightening as a whole, I have to admit that most of the singular scenes would cut away or blur out far too often to win this category. I have to give this moment in terrifying time to a moment from 2017’s IT Chapter One.

While many of the gags in Andy Muschietti’s IT films relied far too heavily on CG to truly grab me, despite a bevy of valiant attempts….this scene, in particular, shook the living shit out of me.

As the Loser’s Club clicks through projector slides in a small dark room, the projector goes haywire and starts clipping quickly through photos. With each projector slide or zoom in to a woman with red hair’s face, the screen flickers to blackness. This creates a sped-up version of the good ole’ Texas Chainsaw Massacre camera bulb gag, to almost a strobe-like effect when suddenly Pennywise pops through the screen, now gigantic, crawling quickly towards the kids as they cowered in fear. All the while, the screen still flickers between black frames and Shaq in a shoe-box Pennywise as he gets closer to the camera. It conjures a literal physical reaction in me to get away from the screen.

Now, I understand many will find this moment as Conjuring-esque, as many of the other jump scares in the two films, but there was something about this moment that genuinely gave me extreme anxiety in the theater….and movies just don’t do that to many very often. Life does. But movies? Not so much.

The perfect balance of unexpected anarchy and size disproportion that royally discombobulated my nervous system. Again, to reference some of the empty Conjuring-type scares, it would have been far more memorable had he actually killed someone at that moment rather than just disappearing into the daylight….but it was still a “wear your brown pants” moment for me, personally.

But still, the true answer is just every time Tim Curry was on screen in the 1990 film.

PENNYWISE MOST ICONIC MOMENT

It has to be the original gutter scene from 1990. Is this not what we all think of every time we’re walking the dog past a storm drain? Hell, sometimes I even smell popcorn in the air and do the little “I have to use the bathroom” shuffle past them…and I’m almost forty years old. Where do you think these dad jokes come from?

I chose the 1990 scene over the remake because although we all know ole’ wet lips Bill Skarsgard does an amazing job as Pennywise, for me there’s nothing that can beat Tim Curry in his Dollar General makeup and bloodshot eyes, looking like someone gave a hobo a bottle of Jack Daniels and a bong hit.

The remake had an amazingly traumatic moment when you see Georgie’s arm get dismembered and then he’s pulled into the gutter…..and admittedly far more frightening than just the slow zoom-in to Pennywise as he looks like he’s trying to make out with you….but once again, CG is these other movies enemy. The wackadoodle face they throw on Pennywise when he goes for the bite completely takes you out of the scene.

What makes the original scene so iconic is that

A) It’s exactly how most of us remember Pennywise in pop culture because it’s such a strange sight…a clown in a storm drain trying to lure kids?…..yet also completely believable. People are messed up out there, guys. In 1990 and 2024. Curry’s portrayal of the clown once again felt all too realistic.

B) Tim Curry’s switch back and forth from charming to completely terrifying. The way he gets excited when Georgie asks if they float will never not give me the heebie-jeebies.

Usually, here’s where I would discuss the best death scene for our iconic horror characters but let’s be honest….both movies had terrible endings. We don’t have to relive that here. I mean who knew you could kill a world-eating killer alien clown by calling him a butthead. Like he’s the opposite of the pink slime in Ghostbusters II? And I think we’re all tired of the “If you don’t believe in the monster, the monster is powerless” horror trope. But hey, that’s how it is and that’s the way it goes.

Nevertheless, Pennywise is one of the all-time scariest horror icons out there and I had a terrible but awesome time digging back into his shenanigans with you guys today. I hope you enjoyed yourselves as well and please comment below, what horror icons would you like to see on “Best of the Bad Guys”? And I’m sure you have some different top quotes, kills, and cool moments so please let us know those as well! Until next time!

A couple of the previous episodes of The Best of the Bad Guys can be seen below. To see more, click over to the JoBlo Horror Originals YouTube channel – and subscribe while you’re there!

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