The creature feeds on children's fear; after Bob confronted it fearlessly, and told it to "go away", he never saw it again.
A tweet posted last week pointing out the similarity between the two stories has been liked more than 20,000 times.
So, could mild-mannered Bob really have clashed with Pennywise as a child? The show's creators, the Duffer Brothers, have recently shed light on how and why they included Bob's story.
"Well, we both have a problem with clowns," Matt Duffer told Vulture. "I've had it my entire life. I had it when I was really little, so when there were clowns at a party, it was a real problem for me.
Then in 1990, we saw the It miniseries and Tim Curry's performance as Pennywise really messed me up. Like, it scarred me in a major way. It was one of the first true horror things I had seen, and I had not experienced Stephen King before.
"That was my first experience with Stephen King, so that was a really huge point in my life. It was two weeks, at least, of no sleep because of that. So yeah, I think [Bob's clown story] was really me describing something that just freaked me out. I didn't have that experience myself. I just had nightmares like that."
Duffer continued: "We were just like, 'It would be cute if [Bob] suggests moving to Maine, right next to Stephen King.' Stephen King exists in this world. Some of the characters have read Stephen King. But Bob definitely does not read Stephen King. He's not interested at all in Stephen King because he hates that kind of story."
If Bob hasn't read the book, why would his nightmare echo it so closely? On first glance, the fact that King's novels exist in the world of Stranger Things makes it unlikely that Bob could have run into a character from one of his books.
On the other hand, Dungeons & Dragons exists in the show as well, but the Stranger Things gang have grappled with D&D-esque "Mind Flayers" and "Demogorgons".
Suddenly, Bob's suggestion that Will's mother and her family should move away from their creepy town in Indiana to sunny Maine with him doesn't sound like such a good idea.