6. The prank war
Going back to the very first season, we get an episode that shows us the Winchester brother bond. The two get involved in a prank war, and there are certainly some hilarious moments. Sam does get some of the best pranks in, such as gluing Dean’s hand to the beer bottle.
There isn’t just one prank that stands out here for the “funniest” moment. Instead, it’s all about the pranks in general. The knowledge that the two leads were getting up to pranks off-screen too certainly adds to the hilariousness of the prank war. True story: the two had to call a truce because they knew they would just escalate against each other.
5. Dodge ball
Dean and Sam went back to school in Supernatural Season 4. This was mostly a Sam-focused episode and a necessary one. We got to understand who would help him realize that he wouldn’t necessarily have to go into the family business, and it offered some beautiful character development for him.
However, there was a Dean moment that stood out. While Sam pretended to be the janitor, Dean would be the PE teacher. With his white shirt and red shorts, he decided it was time for the kids to play dodge ball. And what a scene it was when introducing the greatest game ever invented!