I think it's appeal is two-fold. At least, that's how I experienced it. I grew up in the 80s and 90s and for some reason have always been captivated by the whole woodstock thing - must have seen the movie dozens of times and played the records hundreds of times. I first heared the drum solo on Soul Sacrifice (Santana) when I was about 15. It blew me away and got me determined to play the drums. Got my first kit at 16 and am still playing till this day.
So the appeal of the woodstock scene to me was two-fold.
First, there was -off course- the music. Ow my god, the music.....
I've always found 60s / 70s music, especially from the hippie scene in country, blues and rock, to be extremely inspiring and well-written. It's "real". If you know what I mean. I loved how you could hear a mistake left and right. I loved how the vocals weren't always perfectly on pitch. I loved how the guitar solo's were more about intuition and gut then it was about stringing 64th notes together in the most technical - almost mechanical even-, finger-breaking, manner possible.
That music really speaks to me. It's actual art. I feel the songwriters pain or hapiness or sorrow. Whereas the more "popular" music at the time (80s/90s) was, in my view anyway, extremely shallow and cheap.
I remember a movie clip on youtube from one the perfomances on youtube - I *think* it was Canned Heat - and the most liked comment read "
The 60s.... back when ugly people were allowed to make music". I don't think I could sum it up better then that.
Music today is just like a bad joke, imo.
The second thing that appealed to me I think, in hindsight...
It felt (or feels still...) like Woodstock, from a rock and roll perspective, was like the "ultimate stick-it-to-the-man" event.
And off course, the whole hippie counter culture is simply fascinating. Tragic and perhaps even idiotic in some sense, yet extremely beautiful in another.
Eventhough the entire hippie culture died shortly after that, I think that the cultural impact of Woodstock 69 really can not be understimated. I think the impact was huge. I don't think it's the impact that the hippies hoped for. I think it didn't even make a dent in the things that they really were "protesting" against. Or not a serious one anyway. But I do think it had tremendous impact on the music industry, on art, on human values,... All the things that don't matter in politics, basicaly