1. Big Star -- You have to tell them they were the band of the guy who sang The letter before Joe Cocker did. And then you have to sing the song. If that doesn't work, try talking about "That 70s Show" and the Cheap Trick cover of In the Street. Alex Chilton is hard enough to explain, let alone Chris Bell. Their loss.
2. James Booker -- The typical baby boomer may have a vague memory of Dr. John, but has never heard Booker except on that Ringo Starr album Ringo that they haven't listened to since 1975. You might try telling them he gave lessons to Harry Connick Jr. If you were District Attorney of New Orleans, would you get a homosexual junkie convict to give piano lessons to your son? Only if he were a piano genius too.
3. Syd Barret -- Sure, boomers love post-Syd Pink Floyd, and they know he's the "Crazy Diamond" guy in that movie, but they've never heard his solo albums.
4. Betty Davis -- Yes, the whole world has missed out on Betty Davis, but it's time to wake up. She's the queen of funk.
5. Van Dyke Parks -- The only way to go is to mention The Beach Boys. Their eyes will probably glaze over while you're rhapsodizing about Brian Wilson's SMiLE
6. Patty Waters -- I don't think there's any way to explain Patty Waters to mainstream baby boomers. Even though Diamanda Galas is technically a baby boomer, saying that Patty Waters is her biggest influence isn't going to help much.
7. Skip Spence -- If the don't know Syd, how are they going to have heard Oar by the cracked ex-Moby Grape? About as likely as them knowing who Roy Harper is. [bonus Gen-X-er question: What Minneapolis record store which used to employ Hole/Janitor Joe bassist Kristen Pfaff was named after Spence and Harper's albums?]
8. Townes Van Zandt -- Come on, boomers can barely remember Gram Parsons, can you expect them to know Townes?
9. Nick Drake -- Thanks to the Volkswagen commercial, they are at least that familiar. They still haven't bought the box. Will they ever hear Vashti Bunyan? Or realize that they should own all John Martyn's albums too?
10. Tim Buckley -- Do baby boomers even know who Jeff Buckley is? I guess they slept through the episode of The Monkees TV show where he sang Song to the Siren.
(written June 2007, revised July 2009)