There are two generations of kids who will be fond of It – the ones growing up in the 1990s, and the ones from the 2010s. Since we’re still in 2019, fanfare for It is still through the roof, and with It – Chapter Two's success last year, the hype is definitely still red hot.
With this level of interest for It comes a number of memes from the fanbase itself, and these are funny enough to even make the antagonist Pennywise look like an actual clown. For this list, we’ve considered both versions of Pennywise from the 1990 TV series and 2017's It.
Updated October 19th, 2020 by Christopher Fain. It's spooky season once again, and although there's no new IT film, horror memes are on the rise. While both the old miniseries and recent film adaptation were quite horrifying, the internet has found many ways to make even Pennywise seem funny.
From cooky Halloween images to quirky cameos with other infamous clowns, hilarious Pennywise memes never grow old. This year, there's a plethora of new ones to add to the collection, most of which from the clever content creators of Instagram. If the terrifying clown scares you, strap in for some laughs.
The 27-Year Sabbatical
Even Pennywise takes a day off. According to the book, in fact, he takes a whole 27 years off in-between feedings. It begs the question of what exactly the cosmic entity is up to during this time. Is he really just fast asleep, deep in a cave?
Whatever the case, this funny meme shows that Pennywise more than likely sits back with cucumbers over his eyes and relaxes. Honestly, to get skin that porcelain-like and ultra-clear, he's got to have the best skincare routine in the Stephen King multiverse.
We're All Clowns Here
It was only a matter of time before the Clown Prince of Crime met The Dancing Clown. What better place for them to meet than the now-famous staircase from the recent Joker film? This hilarious meme exhibits Joker showing Pennywise, the new hire, around the office. With a lit cigarette and wacky hair, Joker proves that dear old Pennywise might just be in for a rude awakening at this company.
The best part is that they chose a behind the scenes image of Bill Skarsgård looking a bit sad and confused while in the clown makeup. Altogether, it makes for the perfect scene in an equally perfect meme.
Feeling A Bit Crazy Today?
Everyone wears some kind of mask every now and then. By proxy, everyone also has some subtle hint of crazy within them. This meme pokes fun at that notion by presenting a list of crazy options from a smiling Tim Curry to a neurotic Bill Skarsgård. Every image listed is unsettling in its own right, but each one shows a different type of madness.
Most people probably fall somewhere around a 3 on a typical bad day. They're still smiling, but they're just on the edge of breaking. When they finally do break, it's an immediate jump to 9. That's a level well beyond a murderous clown rampage, too.
What Would You Do For A PS5?
This clever meme is a popular one, using the infamous scene from the story, but replacing the clown's words with something a bit more relatable. In this case, Pennywise offers a PlayStation 5. For a while, the next-generation console was difficult to obtain as pre-orders went live before intended, soon running out of stock.
Desperate PlayStation fans might do just about anything to get their hands on the latest generation console. But will they dive into the sewer with a creepy clown for it? The short answer is yes.
Mom And Dad?
Whenever one looks at Pennywise, they just can’t quite place who he looks like. There’s something about the clown that makes him reminiscent of someone. Well, here’s something to clear up that confusion that’s been knocking you on the head.
Funnily enough, the resemblance is uncanny between Pennywise and these two characters. One of them is the Queen from Alice in Wonderland, and the other is the famous Ace Ventura. More than just appearances, it’s pretty appropriate to think of these two as the parents considering the number of times Jim Carrey and Helena Bonham Carter have played cuckoos onscreen.
Pennywise Has You Covered
On the internet, nothing beats memes. These are like the life source of many internet visitors, and it revitalizes their day to run through the number of insane picturized jokes. So, when Pennywise asks a meme fanatic if they want to join him for a meme overload, then who could resist?
It doesn’t matter if a killer clown is poking his head from a sewer grate, because this guy’s promising you memes galore, and for that reason alone Pennywise is a true friend. After all, can you claim to have a buddy who’s got you covered for all your meme-ing needs?
Enough Terrorizing For Today
The children who grew up with the 1990 It developed a level of immunity toward being scared by Pennywise as they became adults, and this meme (from before 2017’s It) very perfectly shows how these people perceived Pennywise now.
In the 1990 version, the clown was exclusively made through make-up, and the actor was dressed up as Pennywise the whole time. That’s why this clown here looks like a disgruntled Pennywise who’s had his fill of terrorizing kids for the day. You might think that It has nothing better to do than scaring children, but even that character needs to relax once in a while, you know.
Ronald Is Not Happy
Going back to the 1990’s It, that version also drew comparisons to one Ronald McDonald back in the day. The developers of 2017’s It paid their money’s worth on the CGI to make It appear scary when needed the most – although nothing should be taken away from Bill Skarsgard’s performance.
But back in the day, Ronald McDonald had some real competition with Pennywise over who was the more iconic clown. A lot of the kids will agree that the McDonald’s mascot is pretty scary to look at, so it’s not a surprise people would think he tried to branch out and snag the role of titular character for himself. Unfortunately for Ronald, Pennywise beat him to it.
A Look of True Love
Despite Pennywise wanting to eat the children through the whole movie, a little part of us thinks it was fond of those kids at the same time. Think it through, Pennywise rarely ever attacked them straight-up, and would give them enough time to escape as well.
Maybe he had a soft spot for them, and the way he looked at the kids wasn’t particularly scary; one might even call it love. Then again, people do love what they eat, too, so Pennywise might just be staring at the kids as the meal he’s going to enjoy the most. And who doesn’t love a good meal?
Even Pennywise Fears Him
All jokes are off when the almighty Chuck Norris is involved. Pennywise has got nothing on Chuck himself, and there’s no doubt at all the clown hides whenever Chuck Norris appears. In the above picture, you can even see Pennywise trying to conceal himself while Chuck’s boot appears in the frame.
Unfortunately for Pennywise, there’s no way Chuck didn’t know he was right there, and the next picture should be of Chuck literally chucking the clown back to hell. Even when you stop kidding about this, it doesn’t seem realistic for Pennywise to ever be able to beat Chuck Norris in a fight.
Sam's Worst Nightmare
Those who’ve watched Supernatural will bawl with laughter at how appropriate this meme is. You see, Sam Winchester – one of the two protagonists of Supernatural, and the man who single-handedly ended the Apocalypse – is deathly afraid of clowns.
This means that Pennywise is Sam’s worst nightmare come true. Sam is a hunter of all things supernatural, and it’s his job to end ghosts and demons, but Pennywise is one enemy Sammy’s going to be running far, far away from. It’s not all bad, though, you can bet Sam’s big brother Dean is definitely going to end Pennywise, and then sit down to enjoy some pie.
McDonald's New Mascot
In an alternate universe, Ronald McDonald really did get Pennywise’s gig as the antagonist of It and Pennywise himself ended up becoming the mascot of McDonald’s. Now that would be one freaky universe to be a part of, seeing as Pennywise would probably forget about taking anybody’s orders and eat them instead.
This is actually not a bad idea for Pennywise to follow through in the It universe either, as posing as a McDonald’s employee will mean he gets endless supplies of people to lure and chow down. It looks like the creator of this meme unknowingly gave us an alternate ending to It.