Even though this isn’t your conventional “album,” this was still a no-brainer for me. Not only is this among the most successful musical plays ever written, West Side Story is a towering skyscraper of purely musical achievement. By borrowing from atonal music, big band, Latin, standard classical and Broadway traditions, Leonard Bernstein captured lightning in a bottle. Though very much set in 1950s New York, the music here is timeless. “Maria” is one of the most beautiful songs that I’ve ever heard, which is appropriate based on the lyrics, penned by the young Stephen Sondheim. You’re not gonna see me use this word very much: masterpiece.
Silver Medal: Ella and Louis by Ella Fitzgerald and Louis Armstrong
What happens when two iconic jazz musicians get together? Well, often they fight tooth and nail for the spotlight. But on this album, Satchmo and the First Lady of Song have sublime chemistry. And behind the instantly recognizable voices (and trumpet playing), the Oscar Peterson quartet provides the perfect understated arrangement for the standards that fill up the track listing. I can’t imagine what it must have been like to be present for these recording sessions. It would certainly be something you tell your grandkids about.
Bronze Medal: The “Chirping” Crickets by Buddy Holly
It would be easy to discuss how influential Holly was despite only living twenty-two years but this album is on the list simply because it sounds good. You can hear the raw confidence and feeling behind every song on this brief record. Buddy Holly changed the face of music not just because he came at the right time. He was blessed with the ability to communicate the exact sort of attitude that’s behind the best rock and roll. Bruce Springsteen once said he listens to Buddy Holly before each concert to keep himself honest. Snarling, hiccupping and wailing, Holly did things on this record that were often mimicked but never eclipsed.