10 Great Album Covers, Chosen by Tom Kenny of Ogilvy Canada

I don’t think it’s an exaggeration to say that in my teens and early 20s I was addicted to music. I still am, but back then it was a problem. Every Tuesday I would make my way to the local record store and, despite my meager income earned putting posters up around downtown Ottawa, I would typically purchase one to three albums.

What’s important to know, in the context of this list, is that back then most of these purchases required a certain leap of faith. Before the days of streaming, I would regularly find myself buying albums without having heard the music beforehand. Perhaps I had heard a single on the radio, or saw a video on Much Music (basically MTV, but with way more Tragically Hip and probably about the same amount of Alanis Morrissette), but usually that was about it.

With so little known, these purchase decisions were often made based on the scarce amount of information available, and chief among those signposts was the album art. Over the years I made countless purchases based on little more than a cool album cover that for one reason or another signaled that this was an album I needed to own. Of course, sometimes it worked out great and sometimes I wasted $15, but those were the consequences of the high-stakes game of album roulette I had become addicted to.

What follows are 10 records whose album covers I needed to own. 

Drake
Views (2016)

As a Canadian, I would risk having my maple syrup license revoked had I not included at least one Drake album. His album covers are almost uniformly pretty great, but if I had to pick a favorite, I’d go with Views. It’s probably his most ridiculous album cover, but Drake is often a pretty ridiculous artist, so choosing this probably makes sense. Drake is a one-man meme factory, and many of these memes come from his album artwork. But the fact that six years after its release I still see people Photoshopping things onto the CN tower is a testament to the enduring greatness of this particular album cover.

Bob Dylan
Nashville Skyline (1969)

Being Bob Dylan in the early and mid-’60s couldn’t have been easy. He was carrying the weight of an entire generation on his shoulders, and at times you could almost hear that burden of responsibility in his music. You could hardly blame him for withdrawing from touring and the public eye following a motorcycle accident in 1966. When he re-emerged, he had a whole new country-inspired sound with lyrics that seemed more concerned with love than grappling with issues of the day. The warmth and ease of the music is mirrored in Nashville Skyline’s now-iconic album art. With a tip of his hat and a grin to the camera, it shows a man who has embraced rural life with his growing family. Settling down has never looked cooler.

Juvenile
400 Degreez (1998)

To begin, some background … Pen & Pixel is a Houston-based design firm that created the album covers for both No Limit and Cash Money during their artistic and commercial peaks in the late ’90s. According to their Wikipedia page, in a span of about a decade they designed just under 20,000 album covers. As a teenager, I bought many albums whose covers were designed by Pen & Pixel and could never quite decide if they were beautiful or grotesque. Looking back now, I’ve concluded they are both. There are dozens of Pen & Pixel designs I could have chosen to highlight here, but the one I’ve selected is Juvenile’s 400 Degreez. I picked this one both because it is arguably the best album to come out of the No Limit/Cash Money halcyon era and also because it contains many of the well-established signposts of a Pen & Pixel cover—jewelry, scantily clad women, gaudy museum-like setting, and guest features integrated directed into the album art. The only thing missing is some weird, forced-perspective stuff.

The Walkmen
Everyone Who Pretended to Like Me Is Gone (2002)

“Man, I really need to update my Facebook profile pic … I don’t even think I own that shirt anymore. I mean, do I even want a picture of myself for my profile pic? Feels narcistic … That one of me in Cancun is pretty good. I need to start working out again … No, I need something a little more edgy. Something that says to people, ‘Yes, I’m on Facebook, but I don’t really care about Facebook.’ Maybe like, an album cover or something. This Walkmen one is pretty good. Lets people know I like cool indie bands they probably haven’t heard of. Good level of cynicism in the album title. Those kids look pretty badass … Yeah. Let’s do it.” 

Sonic Youth
Bad Moon Rising (1985)

I must confess that of all the albums in this article, this is the only one I’m not really familiar with musically. I came across it while researching Goo, a subsequent Sonic Youth album that I really like and had intended to include in this article. But then I saw this cover art from their second album, released in 1985 and photographed by James Welling. 

As much as I love this album cover, I wish it was the poster for a movie instead. I would like to spend time in this world. I want to see the movie where a flaming pumpkin-headed scarecrow comes to life in the outskirts of New York at dusk, then journeys to the city for a night of murderous tyranny soundtracked by the discordant Sonic Youth. Can someone please make this movie?! I nominate Harmony Korine.

Young Thug
Jeffery (2016)

You can often gauge the quality of a Young Thug album/mixtape by its album art. On the one hand, there are the albums that feel like a clearing out of loose tracks whose cover art usually reflects the same hastily assembled conceptualizations. And then there are the more cohesive musical statements, which are accompanied by some of the coolest album covers of the last decade. And among those, Jeffery is his best. Its cover was shot by Garfield Lamond and features Young Thug adorned in a dress designed by Alessandro Trincone. Young Thug has long pushed the boundary of what is possible for a popular rapper, and this exquisite album cover—and its endless meme-ifcation—likely played a part in making rap music a bit more inclusive. 

Mac Miller
Swimming (2018)

Art can often take on new meaning over the course of time. Swimming was released just a month before Mac Miller passed away. Over the past few years, this album has taken on new meaning and depth for me that I’m not sure it would have, had the artist who made it not died tragically. It was always an engaging cover, but as I look at it today, I can help but be drawn to the look of despair on Mac’s face. And I can’t help but think that his dirty, bare feet suggest an unraveling of some kind. And that the doorway he is slumped in is shaped exactly like a coffin, and the white surrounding it feels like oblivion. It’s a beautiful album cover, and a beautiful album, and I’m sad Mac isn’t making music anymore. 

Hole
Live Through This (1994)

What draws me to this one is the manic tension that is created by its contradictions. The ecstasy of victory paired with tears. The perfect beauty queen who also has makeup streaking down her face. The horror-movie visual language paired with the Barbie font treatment. A depiction of archetypical femininity on an album that challenges those very archetypes. Shot by German photographer Ellen von Unwerth, this album cover has rightly become one of the most iconic of the grunge era.

Grateful Dead
(Self-titled, aka Skull and Roses, 1971)

While the Grateful Dead released only a handful of studio albums, they put out dozens of live albums—some officially, some unofficially. Within this deep catalog, there are lots of amazing album covers to choose from, as well as some really, really bad ones (shout-out to Go to Heaven for being so epically bad that it’s actually pretty great). Rather than go with a deep cut, I chose to go with a classic—their eponymous second live album, referred to by fans as Skull and Roses. The cover was designed by Stanley Mouse and Alton Kelley, who were responsible for several Dead album covers and concert posters, and features an early appearance of Bertha, the now-iconic skeleton wearing a wreath of roses who is named after the song that kicks off this album. 

Johnny Cash
Orange Blossom Special (1965)

Johnny Cash has always seemed more myth than man to me, and albums covers like this are probably the reason why. No human man, made of flesh and blood, has ever sat atop a train, smoking a cigarette, dressed like a hobo Steve McQueen. Everything else about the album art is also great—the lovely Cooper Black-looking font (shout-out to De La’s Stakes Is High, another incredible album cover), the Dutch angle photography, the logo on the side of the train, those boots—it’s all perfect. But it’s Johnny Cash’s effortless outlaw cool that makes this one of my all-time favorites.