In middle and high school, I woke up every day at 5 a.m. to deliver the Trenton Times to about 50 customers in suburban New Jersey via bicycle. It sucked, but was necessary to fund a steady stream of fresh music into my Aiwa 3 disc changer.
Instead of the Sam Goody's at the mall, where they would heavily promote the latest pop albums, I shopped at the Princeton Record Exchange with the other Mercer County teenage music junkies. Because they sold albums from estate sales, the store was curated to encourage kids like me to discover the classics and get excited to find lesser-known artists and genres. It was heaven. After collecting tips from my paper route, I would take the bus (or get my mom to drive me) to the Exchange, where I would carefully decide how to spend my hard-earned money. This was before Apple Music or Spotify or even Napster, so the cover was often the deciding factor in my purchase.
As I write this, it sounds like Normal Rockwell meets '90s nostalgia, and maybe it is, but it's set to a great soundtrack.
Rage Against the Machine
Most album covers were cool images of the artist. This was a burning monk. Curious kids like myself had to find out as much as we could about the image. This research was followed by listening to the album that brought radical politics to the 'burbs—exactly as Rage had planned. Rage Against the Machine, and the follow up Evil Empire, set the political tone for my generation as people my age went to fight in Afghanistan and Iraq just a few years later.
The Dark Side of the Moon (1973)
This winds up on a lot of lists, but for good reason. Never did a cover so perfectly and simply match the music. I also remember the lyrics to "Wish You Were Here" graffitied backstage at drama club. "We're just two lost souls swimming in a fish bowl…" ya know?
Mothership Connection (1975)
Not knowing anything about the music, you would see this cover and wonder what the funk is going on. Luckily, George Clinton and the Parliament Funkadelic never disappoint. Listening to this album, I become that guy with open legs flying through outer space.
Hot Rats (1969)
Hot Rats was a mash of everything a music geek like me loved. It was weird and self aware but also full of virtuosic performances that really hold up. The album fluctuates between guitar solos that would make Bill & Ted weep, jazz riffs, and sometimes what sound like TV game show intros. I'm surprised elements from this album haven't made it into a viral Tik Tok dance yet. With a title like Hot Rats and the woman on the psychedelic pink cover peeping her head from an empty pool, it's just daring you to listen to the album and try to unpack its meaning. Photographer: Andee Nathanson.
The Velvet Underground & Nico
The music of Velvet Underground and the art of Andy Warhol was a reminder that only 50 miles away was New York City. Older copies would rarely show up in the bins at the Exchange; but I feel like it was constantly being remastered so they were plentiful in the new releases.
Give 'Em Enough Rope (1978)
London Calling was a better album, but for some reason this cover is how I associate punk rock. On-the-nose edgy with that DIY aesthetic.
I loved this album. My neighborhood friends and I would play it on repeat from a boombox cassette in the cul-de-sac. The cover image is very clear in its anti-capitalist message, but sometimes that simplicity is what you need to cut through to your audience.
The Freewheelin' Bob Dylan (1963)
Sometimes to be taken seriously you just need to channel James Dean, like Bob is doing on this cover. My dad had this on vinyl, but I wound up also getting a CD copy of it once he sold his old stereo speakers that were attached to the record player.
Bitches Brew (1970)
The album is effortlessly cool like Miles Davis. I would play this when studying, and still play it today when working. The cover art has a feeling of transcendence and meditation that pairs well with deep thought and concentration.
Is This It (2001, international cover)
9/11 and this album will always be how I remember my first year living in New York City. The cover reminds me of Helmut Newton images from an issue of American Photo magazine I had growing up. The U.S. release had a retail-friendly cover and the song "New York City Cops" was removed due to 9/11 sensitivities. Napster, however, allowed me and my fellow NYU dorm residents to rock out to the illicit song. The fact that the cover was too controversial for Walmart made me love it even more.