15 of Hip Hop’s Most Iconic Album Art

By Yvonne Bynoe

Cover art is important to marketing an artist, but, in the days, of online streaming its importance seems to have diminished. Recently, only diehard rap fans weighed in on the new Rick Ross cover art after a more traditional image was selected over one that was fresher and more cutting edge.

When people went to record stores to purchase vinyl albums or CDs, cover art played a key role in the sales process. The cover art on an album needed to be visually interesting so that it stood out in the crowded music racks. Cover art for musical artists is heavily photographed images because it’s also used to either create a brand for a rap artist or solidify the brand of an established artist. The cover art told potential music buyers what the rap artist was about and also where they were from: East Coast, West Coast, or the Dirty South.

Independent rap labels or rap imprints, the under-sourced stepchildren of the corporate record company, often had to “make a dollar outta fifteen cents” when it came to creating their cover art. Frequently, the label enlisted up-and-coming photographers, artists, or friends who were willing to work for free or for a modest fee. The result is that, while the rap artists on this list are exclusively Black American, the photographers and art directors are not.

It takes time to become legendary. So, for that reason, there is no album cover included after 2004. The covers were chosen both for their aesthetics and the impact that they had on Hip-Hop culture.

15. Beat Bop (1983)

Rap artist: Rammellzee and K-Rob

Cover art: Jean-Michel Basquiat

Jean-Michel Basquiat was not only the producer of Beat Bop, he also designed the cover art for original test pressing. The artwork of the record is typical of his graffiti-influenced style with its chaotic clash of imagery and text. The exception was that, rather than using color, it was drawn in black and white. The cover, however, misspelled Rammellzee’s name using only one L instead of two. When Prolific Records released the single, it was without Basquiat’s artwork. The single was repressed in 2001 with Basquiat’s art. The singles with the Basquiat cover art are rare and highly valued.

14. 400 Degreez (1998)

Rap artist: Juvenile

Cover art: Pen and Pixel

Juvenile’s 4X platinum album, 400 Degreez, with hits such as “HA” and “Back That Azz Up” epitomizes some of the best Southern rap of the 1990s, and the cover art for the album is one of the best of its genre.  Cover art design coming from Southern labels such as Cash Money Records, No Limit Records, Rap-A-Lot Records, and Suave Records was all about bold colors, bling-encrusted lettering, and photographs superimposed on lavish backgrounds; many of these covers were designed by Pen & Pixel.

Pen & Pixel was a company formed by brothers, Sean and Aaron Brock, who, in the early 1990s, worked at J. Prince’s Houston-based Rap-a-Lot Records as a graphic designer and general manager, respectively. In a 2014 interview, the Brock Brothers stated that they had worked with 6,000 to 8,000 clients, producing approximately 19,180 covers during their 11 years of operation.

13. Madvilliany (2004)

Rap artists: Madvillian (MF DOOM and producer, Madlib)

Photographer: Eric Coleman

For those not familiar with MF DOOM, he always wore a mask. MF DOOM told The New Yorker in a 2009 interview that wearing a mask “came out of necessity.” “I wanted to get onstage and orate, without people thinking about the normal things people think…”

This stark monochrome portrait of Doom in a trademark mask was the idea of art director Jeff Jank. Jank was inspired by the grotesque face that appears on the cover of the 1969 album, In the Court of the Crimson King by English rock band, King Crimson. Madonna’s 1982 self-titled debut album influenced Jank’s decision to add a small orange block as a distinctive element. Madonna’s album cover also was a primarily black and white design except for the letter O in her name, which was colored.

12. Stankonia (2000)

Rap artists: Outkast (Big Boi and Andre 3000)

Cover art: Michael Lavine

Stankonia marks an evolution in Outkast’s content with songs such as “Bombs Over Bagdad” and “Gasoline Dreams,” critiquing wars over oil in the Middle East and the problems of modern life. To match the serious subject matter on the album cover, the Atlanta duo moved away from their prior two albums’ illustrated cartoons, opting for stripped down realism.

The album cover, photographed in downtown Austin, Texas shows Andre standing shirtless facing forward, arms stretched outward and his chin up as if casting a spell. Beside him, Big Boi stares directly at the viewer wearing a simple white t-shirt and one chain and pendant. Most striking is that they’re positioned in front of a stark, black-and-white American flag that hints at a separate and different America.

11. The College Dropout

Rap artist: Kanye West

Cover Art: Eric Duvauchelle

The cover artwork for The College Dropout was designed by Eric Duvauchelle, who was part of Roc-A-Fella’s in-house brand design team. It features the famous “Dropout Bear,” which also appears on the covers of Kanye’s first three albums. For The College Dropout, the Dropout Bear sits on a set of bleachers inside a golden frame. Rumor has it that Kanye was firm about his face not being visible. The bear mascot suit just happened to be sitting around in the gym they used for the photoshoot, so it was used. Kanye requested classical gold ornamentation for the design of the cover.

In terms of backstory, Kanye became a sought after music producer when he was in school at the American Academy of Art, where he had gotten a scholarship to study visual art. Kanye has been quoted as saying that he dropped out when he realized that he would “never be one of the great visual artists of the world” and didn’t want to end up working for an advertising agency.

10. Enter The 36 Chambers (1993)

Rap artists: Wu-Tang Clan

Cover art: Daniel Hastings

This album cover broke the mold for rap crews by having Wu-Tang members wear masks. Prior to it, the norm was to have a group photograph with every member trying to look as menacing as possible. People speculated that the masks represented a unified Wu-Tang front instead of any one member getting the spotlight. Others believed that the masks alluded to their pasts as stickup kids. The truth is less exciting. Masks were used because several Wu-Tang members failed to show up for the photo shoot, so everyone wore masks so that people from their management team could stand in for the missing rap artists.

9. When Things Fall Apart (1999)

Rap artist: The Roots

Cover art: Kenny Gravillis

The album’s title is from Chinua Achebe’s novel of the same name, which is taken from the phrase found in William Butler Yeats’s poem “The Second Coming,”  and it sets the tone for social commentary that the Philadelphia-based rap group delivered for their fourth studio album.

The album cover art is monochrome with the title of the album “things fall apart” etched in red. The photograph shows people running away from the police and focuses on the anguished face of the woman in the foreground. The original, uncropped photograph was taken in August 1964 in the Brooklyn, NY neighborhood of Bedford-Stuyvesant during a riot. The unrest began in Harlem after the fatal shooting of 15-year-old James Powell by a White policeman then spread into Brooklyn.

8. 3 Feet High and Rising (1989)

Rap artists: De La Soul (Posdnuos, Trugoy the Dove and Pasemaker Mase)

Cover art: Toby Mott/Grey Organization

3 Feet High and Rising Feet was the debut album of De La Soul, and it ushered in a new era in rap music: The Daisy Age. De La Soul was often referred to as “Alternative” rap for departing from Hip Hop’s established norms, sonically and sartorially. In a rap music landscape filled with aggressive Alpha men wearing gold rope chains, De La Soul gave off black bohemian vibes, unapologetically representing Beta men. The group also opened the door for groups such as PM Dawn (1991), Arrested Development (1992), and The Pharcyde (1992).

Tommy Boy Records hired the British art collective, Grey Organisation, to develop the album’s brand aesthetic, which was defined by a bright, neon palette and a pop-art sensibility. In his essay, “Hip Hop in The Daisy Age” for Snap Galleries, Art Director, Toby Mott, stated that they set out to “move away from the prevailing macho hip-hop visual codes which dominate to this day.”

In September 2020, Sotheby’s sold the Mott’s Study for the cover of 3 Feet High and Rising (1988) for $21,400; the pre-auction estimate had been $2,500-$3,500.

7. Paid In Full (1987)

Rap artist: Eric B (DJ) and Rakim

Cover art: Ron Contarsy 

Paid In Full, the debut album of Eric B and Rakim, is universally acknowledged as not only a classic rap album but also a groundbreaking one. Nas, considered by many to be the heir apparent to Rakim has said that Paid In Full “[p]ut the streets to music.”  In 1987, this album raised the bar lyrically for how a serious rap album should sound and it helped to cement New York City as the then-leader of the rap world.

Aesthetically, the cover art for Paid In Full also created the template of how a rap artist should look. The legendary photograph shows the duo standing in front of a pile of money. Before there was a Sean “Puffy” Combs, Eric B and Rakim were flashing cash, dripping in gold chains, and wearing their custom-made Dapper Dan outfits.

6. Liquid Swords (1995)

Rap artist: GZA

Cover art: chief artist, Denys Cowan; digital artist, Jason Scott

According to GZA, the image for Liquid Swords came to him while playing chess against fellow Wu-Tang Clan member, Masta Killa. He said that the two had played more than 30 games while smoking weed. It’s during this chess series that GZA had the vision of the chess pieces coming to life and battling one another. Artist, Denys Cowan, created the original drawing and digital artist, Jason Scott, added to the development of the final work.

5. Beats, Rhymes and Life (1996)

Rap artist: A Tribe Called Quest

Covert art: MC SKAM2

Beats, Rhymes and Life isn’t considered a successful album for A Tribe Called Quest. Lyrically, it departs from previous albums with a more serious tone and it also hints at the cracks developing among the group that eventually led to its demise. The cover art, however, is a beautiful example of the trio’s Afrofuturistic aesthetic.

The illustration was created by Miami, Florida native MC SKAM2 who made the album cover art for ATCQ after running into Q-Tip. At the time, SKAM2 was living in New York City and pursuing his music career. The vibrantly illustrated cover depicts a striped woman carrying a flag in what appears to be a post-apocalyptic city. Following the figures that appeared on the prior ATCQ album covers, the woman is primarily painted in red, black, and green, signaling the Pan-African colors. However, rather than peaceful or seductive, as she had been rendered previously, the female figure appears angry and ready for battle.

4. Return to the 36 Chambers: The Dirty Version (1995)

Rap artist: Ol’ Dirty Bastard

Photography: AlliODB remains one of most unique figures in Hip Hop history. He was one of the break-out stars of Wu-Tang Clan known for his quirky, comical and outlandish lyrics and behavior.  It stands to reason that he’d give us one of the most iconic album covers of all time: a copy of his Public Assistance identification card with “The City of New York” replaced with Brooklyn Zoo. In the days before EBT, Ol’ Dirty Bastard was keeping it real.

3. Ready To Die (1994)

Rapper: The Notorious B.I.G

Photographer: Butch Bel Air

Although the artwork for Ready to Die is clearly borrowing from Nas’ Illmatic cover released six months earlier, there is one important difference: The baby isn’t Christopher Wallace but rather Keithroy Yearwood. The then 18 year old reportedly was paid $150.00 for use of his photograph because of his “giant afro.”

The cover’s simplicity, with its all-white background, is a departure from the glitz and gold that was often part of Hip Hop imagery during the 1990s. The design also sends a hauntingly prophetic message about the future of Black men in the United States by positioning a happy baby, who resembles a young B.I.G above a headline that reads “Ready to Die.”

2. Reasonable Doubt (1996)

Rap artist: Jay-Z

Cover art: Jonathan Mannion

On the cover of Reasonable Doubt, Jay-Z’s debut album, as if avoiding the paparazzi, his tilted brim shields his face and all the viewer can see are the symbols of his success: a Cuban cigar and a gold pinky ring. Similar to John “The Teflon Don” Gotti who changed the image of Italian mafiosos with his tailored suits, 26-year-old Jay-Z elevated the image of the rap artist from that of a corner boy to one of a boss.

Jay, who was older than most debut rap artists, was allegedly already a millionaire from his street pharmaceutical sales. This gave Jay-Z power and autonomy, and separated him from the struggling young rap artists scrambling for deals and  jumping through hoops to keep them. By co-founding Roc-a-fella Records with Damon Dash and Kareem Burke, Jay-Z wasn’t taking orders from the label; he was the label.

The cover art supervised by Cey Adam’s is the personification of Jay-Z’s quote: “I’m not a businessman. I’m a business, man.”

1. Illmatic (1994)

Rap artist: Nas

Photographer: Uncredited

“To every baby on the album cover existing’/This trend I was settin’ it came to fruition.” — Nas, “Nas Album Done,” on DJ Khaled’s 2016 album, Major Key

Lyrically, Illmatic has stood the test of time and remains that standard for rap artists intent on storytelling and not just stringing some words together. Moreover, the cover art has inspired a host of Hip Hop greats, including The Notorious BIG and Lil Wayne. Queensbridge Housing Project is an important element in Nas’ biography insofar. It’s where he’s from and it was important to establishing his worldview and also his determination to transcend it. Nas acknowledges its relevance to his life by using it as the backdrop of his debut album with a photo of himself as a child in the forefront.

Illmatic is the G.O.A.T. of rap music album covers, because we’re still seeing babies on album covers 27 years later.

We wanna know what your picks are? Did we miss any?  Let us know.

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Yvonne Bynoe is the founder of the online platform @shelovesblackart which highlights visual art from the African diaspora with the mission to encourage more people of African descent to collect art. She is a cultural critic and author of several books on popular culture.

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