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I believe Metallica would be the '08 classic headliner since they are in the Rock and Roll Hall of Fame. Pearl Jam will be there as soon as they are eligible which should be in about 5 or 6 years.
Luckily for us that was a "classic rock" Metallica show in '08. The fact that 13 of the 18 songs they played were from the first 4 albums/older covers makes it classic rock in my mind.