- Big-Lipped Alligator Moment: Sha Na Na. Not just because they were an obscure campy cover band amid all the rock heavyweights, but they didn't even have a recording contract at the time.
- Crowning Moment of Awesome: The Who's "See Me, Feel Me" scoring the sunrise!
Listening to you I get the musicGazing at you I get the heatFollowing you I climb the mountainI get excitement at your feetRight behind you I see the millions
- Crowning Music of Awesome: Look at this list.
- First Installment Wins: While Woodstock '94 had great sets such as Metallica, Aerosmith, Bob Dylan, Green Day, Primus, and a career making performance by Nine Inch Nails, it's usually considered to be far inferior to the original, and as for Woodstock '99, well...
- Critics only praised Woodstock '99's less aggressive/non-metal acts, but all of these performances were both less remembered than 1994's and were completely overshadowed by the violence at the end of the festival. The more fondly remembered sets included George Clinton, The Tragically Hip, Jamiroquai, Los Lobos, G. Love & Special Sauce and one of James Brown's last great performances. The '99 festival was also notable as the first major American concert by Muse...who played on the "Emerging Artists Stage" to almost no attention.