4. Insane Clown Posse
What do you mean, you forgot that ICP performed at Woodstock 99? The Clowns' stage show may have suffered a bit from a distinct drought of Faygo, but the novelty of ICP perverting the fest's corporate co-option of music and peace with cogent protest songs such as "Fuck the World" remained sweetly delicious. The very next year, ICP would begin working to recreate a little bit of the Woodstock magic with their very first Gathering of the Juggalos.
Jamiroquai never quite achieved the megawatt superstardom in the U.S. that they did across the pond, and part of the reason may be that their stellar Woodstock set was so thoroughly overshadowed by the gnarly "Break Stuff" vibe of the chaos to come. Which is a shame, not just because Jamiroquai put on a great show, but because dozens of other artists throughout the festival's schedule delivered great, positive music and showed fans the time of their lives.
2. Rage Against the Machine
In the event's aftermath, the media had a bit of a tough time with Rage Against the Machine's set at Woodstock 99. The band was a critical darling, the thinking man's nu-metal, but it was highly tempting to blame the carnage that capped the concert on Rage's anti-authoritarian rabble rousing.
The band had burned an American flag onstage, and the flames sure looked pretty. Luckily, Fred Durst became the all-too-willing lightning rod for criticism of the lineup's metal contingent, and Rage's excellent set is remembered fondly by comparison.