These Timeless Album Covers Captivate Fans of Every Generation

The Clash, Big Star, X, Neil Young and more

I grew up in a house where music was the only constant. An aunt worked at Capitol Records, so every holiday, birthday or visit included stacks of records. You might hear Peggy Lee followed by the Beatles, leading to Sinatra, capped off with Merle Haggard.

This continues today. There is always a record on. Which is either a good thing or a bad one, depending on what I’ve picked. I can be a real pain in the ass when it comes to music selection. The family has learned to deal with it. I like to think of it as curated taste.

In my experience, a great record has a great cover. The two are forever linked. If you’re an artist who cares deeply about each note and every lyric … you probably won’t settle for some crap cover art. These are some of my favorites.

Neil Young, Time Fades Away (1973); On the Beach (’74); Tonight’s the Night (’75)

Right out of the blocks, I’m cheating. I’ve jammed three albums into one pick. These albums make up Young’s legendary “Ditch Trilogy” and were designed by the late Gary Burden. They came on the heels of Harvest, The album that made him a superstar. Fans looking for a sweet follow-up encountered three of the darkest, bleakest, most brutally honest and harrowing LPs in rock history. They’re also three of the greatest. Every artistic and aesthetic choice I’ve made since is rooted in these records. Without them, we don’t have Nirvana, Pearl Jam, Sonic Youth, Wilco, Elliott Smith, Cat Power, Lucinda Williams, Jason Molina, Big Thief, Dinosaur Jr. … I could fill the page. We’d also be stuck wearing khakis and listening to Maroon 5.

X, Los Angeles (1980)

I’m biased because I grew up in L.A., and the sound of this record filled every hallway in my college apartment building. We’re just on the other side of punk, and Hollywood is a messy playground full of cast-offs. John Doe and Exene were the king and queen. The cover photo by Bob Biggs captures just what it felt like to live in L.A. during that time. Dark, sinister, Santa Ana winds blowing, hills burning and earthquakes splitting freeways in two.

The Clash, London Calling (1979)

This cover, designed by Ray Lowry with a photo by Pennie Smith, was a direct nod to Elvis’ first album and had almost as much impact. For many, The Clash was the greatest band in the world during their 7 or 8-year heyday. Joe Strummer was a poet, the British stepson of Johnny Cash. The photo of Paul Simonon smashing his guitar on the cover became one of the most iconic in rock history. If you haven’t listened to these discs, you are definitely doing it wrong.

Big Star, Radio City (1974)

A William Eggleston photograph of a bare light bulb in a seedy red room might seem like an offbeat choice, but Big Star might be one of rock’s most offbeat bands. It was said that everyone who bought a Velvet Underground album started a band. The same could be said for Big Star. They were power pop rockers who also made brooding ballads. Their leader was a surly, rebellious “fuck you” type that lived the kind of self-destructive, tortured artist life that led The Replacements’ Paul Westerberg to pen the perfect ode “Alex Chilton.”

Sonic Youth, Goo (1990)

From artist Raymond Pettibon. He got his start in punk rock, making art for his brother Greg Ginn’s band, Black Flag. I was scared to death of that party, but Sonic Youth played the kind of dense, discordant guitar music I could get behind. They also projected a kind of downtown NYC cool that a suburban Valley Boy could latch onto. They followed this up with other covers by Mike Kelley, Richard Prince and Gerard Richter. That’s some serious artistic cred.

Bonnie “Prince” Billy and Matt Sweeney, Superwolf (2005)

I have more Bonnie “Prince” Billy albums than any other artist not named Neil or Bob. He is an extraordinary songwriter who mines every uncomfortable theme and emotion imaginable. The music is steeped in sex, violence, loneliness and blood. This drawing by Spencer Sweeney of a bloody hand emerging from the ocean pretty much sums it up.

Low, The Great Destroyer (2005)

The image is as grand in scale and thunderously bold as Low’s sound. The Zak Sally painting could depict billowing storm clouds of plumes of wildfire smoke. Either interpretation matches the feeling Mimi Parker and Alan Sparhawk create with their thick walls of guitar, hypnotic drone and atmospheric ambiance. “When I go Deaf” might be one of my favorite songs with an ending that’s worth the wait.

Thelonious Monk, Monk’s Music (1957)

This was the first jazz record I ever bought. There are countless great jazz covers I could have chosen. But this weird photo by Paul Weller of Monk in shades smoking a cigarette while sitting in a kid’s wagon was cool as shit to me. Hard bop was a completely new world. Coltrane, Coleman Hawkins and Art Blakey all played on this album. It was my gateway drug, and I never looked back.

Big Thief, Dragon New Warm Mountain I Believe in You (2022)

They are the best band in the world right now. I love the cover because it looks like I drew it. (If that sounds narcissistic, check out the last entry on this list.) Adrianne Lenker’s weird sketch of odd animals playing music around a bonfire could just as easily describe the band itself. Lenker writes songs like Joni Mitchell, and the band sounds like Crazy Horse played by Nirvana. Enough said.

Tom Brosseau, Grand Forks (2007)

Upon arrival in Hawaii on a family vacation, my phone was filled with messages from my friend Tom. He’s a wonderful folk singer who writes odd traditional ditties about floods, ghosts, whiskey, and North Dakota. His label just showed him the artwork for his new record, and he HATED it. He asked if I’d be willing to help. “Of course!” I said. “We just landed in Hawaii. When do you need it?” …. “Tomorrow??” was the answer. I listened to the record sitting on the floor of my hotel bathroom and drew using a pencil, hotel stationary and iced tea I spat on the paper to smudge it. I sketched out drawings of guns, empty whiskey bottles and slot machines. The lonely guy at the bar reminded me of Tom. Not a bad start to a vacation.