I don't know if it was the way they filmed it, or the fact that they were so casual and normal around the cameras, even the setups for the scenes were kind of goofy and "home video" style.
They quickly realized that people liked the filler as much as the actual content and capitalized on that interest with Jackass.
It felt authentic because it was. The people making the videos had a genuine connection / were actually friends, and were really just doing it for fun in the beginning and that makes it feel different than a lot of the manufactured content that people are exposed to today.
Videowise, there was another skate vid during that period called "Whisky: The Movie" that was in the same hilarious vein as the Jackass stuff. Looks like it might have been DMCA'd off of youtube.
It's really just a group of people making funny content. They feel genuine and that draws people in.
I find now they're more mature and aware of their influence. I watch mostly because it's just fun to watch them have a great time (you can tell they really enjoy their job and that makes it for me).
There was a while there where it was genuinely upsetting to see some of those people. They really didn't understand the difference between pranking a friend that's opted in to the behavior and random people in public, and what's acceptable as a prank in both instances.
I'm sure Jackass had a few misses in this department too, but at least by the time they were famous the public stuff seemed more along the lines that might leave public people that saw it or were unwittingly involved thinking "WTF did I just see" or a story that later they would start with "You wouldn't believe the stupid person I saw today" and if the person realized it was a prank would generally think it was rather funny since it didn't affect them.
Contrast that with youtube "pranksters" of the time when they first started being popular physically assaulting people, or stealing things, or tricking someone into thinking they had lucked out and then making them feel the loss of that when it was shown to be fake as well as humiliating them in front of the world. "Haha you thought that $100 bill was real? Psyche! It's fake, you didn't find anything! Hey everybody, look how sad he looks now. Why are you sad, bro? It's a prank, be happy, the whole world is watching!"
I remember having to very carefully counsel my young son who kept stumbling on them and watching them on why these people weren't being funny, they were being mean, and this wasn't how people should be treated.
CKY had a few bad ones though (throwing a life-sized doll off a motorway in front of cars is a good example of a bad one...) but they seemed to grow out of it.
I laughed at some of the jokes on each other but the ones involving innocent bystanders were almost all just horrible.
This can also be seen in the Trailer Park Boys TV show. Seasons 1-7 under the direction of Mike Clattenburg do have a lot of swearing and dirty jokes, but it is always genuinely good humor, or serving plot and character development maybe. I'm sure I don't describe it well, but "I know it when I see it."[0] The following seasons with other directing/production have lost that tact and restraint; like they just call someone 5-6 dirty words in a row, funny only for the shock value of the words. Not funny.
This is a great point, so maybe they were also among the first to attract the sort of parasocial relationships that also emerged with the rise of social media.
Maybe I'm misreading the situation, but I'm pretty sure political AM radio show hosts beat them to that. Casual, conversational, "unlike those morons, you and I both know..." style, tons of in-jokes. Extensive call-in segments.
Their laughter invited you to laugh with them.
Makes me think of Filthy Frank, he was one of the worst. But it had some great fourth wall breaking moments, when they crack up themselves after idk, a neighbour yells at them for screaming from the roofs in the middle of the day.