The first CD should start with Robert Johnson and Bessie Smith and Big Mama Thornton.

Then it should have, uh, Louis Jordan, Bo Diddley and Little Richard.

Definitely Dean Martin, Sinatra, Johnny Cash, Patsy Cline, Elvis, Buddy Holly, Bobby Darin, Grateful Dead, Iron Butterfly, Canned Heat, Beach Boys, Stevie Wonder, Steely Dan, Billy Joel, Ray Charles, Carpenters, Jim Croce, Cat Stevens, Huey Lewis & the News, Bruce Springsteen, Hall & Oats, Devo, Bruce Hornsby, Van Halen, John Melloncamp, Sade, Stevie Nicks, Toto, Anita Baker, Dire Straits, Tina Turner, Jimmy Buffet, Nirvana, Heart, Boston, Cheap Trick, Neil Diamond, MC Hammer, Santana, Lenny Kravitz, Red Hot Chili Peppers, TLC, Shania Twain, Journey, Melissa Etheridge, Missy Elliot, Dr. Dre, OutKast to name just a few.

if he likes edgier fare, you might want to have a look around the web for d/ls to ,'Lux & Ivy's Favorites' . its a collections of old roots, rock & blues songs from the birth of rock n roll

Louis Armstrong, Ella Fitzgerald...

Also needs huge chunks of the motown catalog.

Not to be all child of the 80s, but: Madonna, Prince, Michael Jackson.

Bob Wills, The Ventures, Los Lobos, ZZ Top, X.

The Turtles, The Mamas and the Papas, The Byrds.

War, Parliament/Funkadelic, Sly and the Family Stone, The Meters, Earth Wind and Fire, Head Hunters.

Canadians: The Band, Neil Young, Joni Mitchell.

You could also have him listen his way through jonmc's blog.

I'd be a bit disappointed to receive an American Rock compilation that included Cat Stevens or Dire Straits.

(Though, that said, I'd be more disappointed to receive one with MC Hammer...)