10 Classic Album Covers to Entice Your Senses

Ani DiFranco, Dave Matthews Band, Cat Stevens and more

I am an absolute music geek and this could have easily become a rabbit hole I never climbed out of. I own over 4,000 albums on vinyl. My CD collection might eclipse that number—I just haven’t cataloged them yet.

I don’t know if this is my actual Top 10. I’d probably need to go on a four-month excursion to truly land that list. The stories behind the 10 below just seemed to flow.

I love album art. I adore music. And I find the tie between the two mesmerizing.

Phish

Rift (1993)

I came into Phish by sifting through my older brother’s CDs. I was enthralled by this cover the moment I saw it. My favorite color is blue, so it had an immediate pull. The art was so unique, and as I listened, I began to realize that every element referenced lyrics from the songs. That record ended up shaping how I wanted my guitar playing to sound. And the cover taught me how important visuals can be in enhancing the album experience.

Jimi Hendrix

Band of Gypsys (1970)

My older brother had just graduated college and was preparing to travel cross-country in a beat-up van. We were driving when he popped in this CD. There it was: The fiery character with a guitar, bathed in red, yellow and green light. Then the music kicked in and I heard, “An old friend with a brand new name—the Band of Gypsys!” The artwork spoke to the rebellion that 1970 represented, and the track “Who Knows” just poured from the speakers. I still obsess over that album and own five different versions on vinyl.

The Smashing Pumpkins

Mellon Collie & the Infinite Sadness (1995)

This was the first double-CD package I ever saw, and the art was outrageous. I stole it from my older sister’s room and played “Bullet With Butterfly Wings” on repeat. The contrast blew me away—beautiful, ornate artwork paired with raw rebellion and poetic angst.

Cat Stevens

Tea for the Tillerman (1970)

The visuals feel like an invitation to a magical kingdom where you’re going to learn a few life lessons. And that’s exactly what the record delivers, especially on songs like “Father and Son” and “Wild World” Those tracks can guide you through life, just like a great children’s book.

Dave Matthews Band

Under the Table and Dreaming (1994)

When I saw this super-cool cover, not realizing it was a vintage carnival wave swinger, I popped the CD in. The first thing you hear is that killer snare drum roll on “The Best of What’s Around,” and I was immediately hooked. Years later, while interning at EMI, I met the guy who designed the cover, Thane Kerner. I couldn’t get three words out without stuttering.

Everlast

Whitey Ford Sings the Blues (1998)

My first musical love was hip-hop—I used to scratch records in grammar school. By sixth grade I had a guitar but still loved hip-hop and had no idea where I fit in. Then here comes this guy, tatted up, wearing a cowboy hat with no sleeves, smoking behind the door of a beat-up truck. It was acoustic and soulful. It rocked. But it also had the hip-hop spirit I’d grown up with. Everything clicked. For about two years, I wanted to be Everlast.

Ani DiFranco

Dilate (1996)

My mom knew I lived for music, and she’d drop me off at the used CD shop while she and my sister ran errands. I’d dig through the bins for hours, then bring anything interesting into the listening booth. I’ll never forget pulling out a CD with a young woman on the cover—dreadlocks woven with streaks of green and blue. I expected hard rock. Instead, I heard the most ripping acoustic guitar, paired with an angst-ridden voice that carried sweetness and soul. Lyrics like “F*** you and your untouchable face” sounded like heartbreak—but not surrender.

Bob Dylan

Blood on the Tracks (1975)

I knew nothing about classic rock or folk. But the day I saw Blood on the Tracks sticks with me. Was it the painterly cover? The word “blood” in the title? Or maybe seeing a song called “Idiot Wind” on the back? Either way, my life was forever changed. That album lives permanently in my desert-island Top 5 and remains a beacon for songwriting perspective.

Arrested Development 

3 Years, 5 Months and 2 Days in the Life Of… (1992)

The cover felt like a labyrinth. Then I saw them on TV—maybe In Living Color—with the guy dancing around holding an umbrella. It was mesmerizing. A total circus of culture. I was the only third grader I knew who could rap every word of “Dawn of the Dreads.” That album introduced me to roots music, soul and R&B and the common thread that ties all music together.

Frank Sinatra

In the Wee Small Hours (1955)

In 2017, while touring as an opener for Allen, Mack, Myers, Moore, we played SPACE in Evanston, Ill. Backstage, in their huge green room, there was a turntable and a carefully curated record collection. Zack Mack pulled out In the Wee Small Hours. I looked at it funny—like, what’s that? He put it on, and my heart absolutely melted. It was lonely. It was heartbreaking. That voice, living inside such an intimate, emotive record—it wasn’t hit-driven, it was pure feeling. The cover drew me straight into what became one of my all-time favorite albums. It’s often credited as the first “concept album,” which blows my mind—and feels completely right.