Release date: Nov. 24, 2008
Photography: Danny Clinch
Art direction: Virgil Abloh, Willo Perron, Kris Yiengst, Brian Donnelly (KAWS)
Labels: Roc-A-Fella, Def Jam

Kanye West decided to encapsulate the many shades of heartbreak in his daring fourth album, 808s & Heartbreak, the revolutionary cover that tops our list. In this humorless 13-track production, West isolates himself from the bold and boisterous songs of his previous records, and the outcome is a stark contrast from anything he had ever done before, both sonically and visually.

The original album cover features nothing but a deflated heart and a strip of subdued, Graduation-reminiscent swatches. Save for the pop of the heart's red hue, photographed by Kristen Yiengst with art direction by Virgil Abloh and Willo Perron, the cover lacks the loudness West usually exhibits in his visuals. Kanye's minimalist approach was groundbreaking at the time. This stripped down look may not have been entirely new, but Kanye was the first artist to successfully pull off and popularize such an aesthetic. In fact, without 808s & Heartbreak many of the other album covers on this list would not exist.

The gray, relatively bare cover evokes both emptiness and vulnerability. It's an appropriate cover for one of the rapper's most introspective albums, detailing his thoughts about splitting with his fiancé and dealing with the death of his mother.

The vulnerability is evident, and the deluxe album cover of 808s and Heartbreak by KAWS takes it a step further. West had KAWS incorporate the visual artist's iconic gloved hands onto Yiengst's original photo of the deflated heart. Unlike the original cover, there's more life in this version. The panel of colors on the side appear stronger and more vivid. There's something more urgent and poignant in the forceful tearing of the already-crushed heart. This cover alone is a testament to West's talent, that even in his darkest moments, he's able to deliver a brave, honest, and relatable album that challenges everything he had ever done before and influenced the next generation of rappers, from Drake to Future. At number one, 808s & Heartbreak leaves an undeniable mark on the history of album art. —Susan Cheng

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