Chapter 1: Breaking Barriers (1986-1990)
“I wear my adidas when I rock the beat…” - Run-DMC

In 1985, on the back cover of his debut album, Radio, LL Cool J wore a pair of Air Jordan Is. It was only right that the hottest new rapper in the game would rock the hottest young athlete’s new kicks. LL was a sensation, with a fresh sound and unrivaled charisma who could've sold any product, but it was his established Def Jam labelmates who would go on to kick-start the collision of the rap and sneaker worlds.

In the mid-1980s, as Run-DMC was breaking barriers and garnering worldwide acclaim, adidas executive Angelo Anastasio came upon the members of Run-DMC breakdancing in their adidas “rainsuits,” their slick three-striped tracksuits that were ideal for spinning on cardboard. Anastasio didn’t realize the true depth of Run-DMC’s influence until he went to one of its shows at Madison Square Garden and saw thousands of rabid fans in the crowd waving their adidas shoes and apparel in unison. He knew there was so much untapped potential.

Anastasio offered them a $1 million endorsement deal, a landmark deal at the time. It was the first time a brand was prominently featured in rap music videos, with the adidas Superstar getting camera time in Run-DMC and Aerosmith’s smash, “Walk this Way,” then getting top billing on Run-DMC’s 1986 song, “My Adidas.” It was the first time a sneaker company ever had its own rap song. The group was the most successful rap act in the world and adidas—specially Run-DMC’s shoe of choice, the Superstar—was thriving.

“I gave them $1 million but they ended up generating sales of more than $100 million over the next four years,” Anastasio recalled in Sneaker Wars, Barbara Smit’s book about the complicated history and rivalry of the brothers who went on to found adidas and Puma (a must-read for any sneakerhead). “At a time when Nike was growing like crazy, the endorsement gave adidas exposure and kept the brand alive in the eye of the public.” Anastasio estimated that adidas sold an extra half million pairs of Superstars thanks to the Run-DMC co-sign.

The success of this pairing was huge for many reasons. For one, no hip-hop act had ever secured a million dollar endorsement deal before, and no sneaker company had ever invested these kinds of resources into a hip-hop act. The German giant recognized that rappers influenced the youth and smartly tapped into that market in a way its competitors had yet to realize. Run-DMC connected because they dressed the same way they would on stage and in videos as they would on their corner in Hollis, Queens. While earlier rap acts like Melle Mel and Afrika Bambaataa wore flashy leather or elaborate African-inspired attire, Run-DMC kept it simple and authentic.

Even with the initial investment in Run-DMC, adidas still may have undersold their influence and effect on sales. Run-DMC was able to singlehandedly aid adidas in their competition with Nike and, most notably, Michael Jordan, who was rapidly ascending in 1986—a year after the Jordan I debuted and the year “My Adidas” was released.

By 1989, Jordans were featured prominently in Spike Lee’s film, Do The Right Thing. Along with Lee’s famous Mars Blackmon commercials, the sports and entertainment worlds were continuing to successfully mesh together. Conventional entertainment avenues and sportswear had merged so seamlessly that, in 1990, MC Hammer was able to ink a lucrative endorsement deal with British Knights.

British Knights had previously tapped Kool Moe Dee to wear their product in his music videos on MTV (as well as Public Enemy) but the deal with MC Hammer was on a much larger scale. British Knights signed Hammer to a full endorsement deal at a time when he was one of the biggest names in pop music. The company sponsored his tour, did in-store events and contests, as well as TV, print and radio ads. He immediately pushed British Knights into a more mainstream market and it proved to be a mutually beneficial relationship until the brand folded in 1992.

Chapter 2: Missed Opportunities (1990-1996)
“I sport New Balance sneakers to avoid a narrow path…” - Phife Dawg

Heading into the 1990s, the rap and sneaker industries were shooting into the stratosphere. The west coast rap scene was reaching new levels of sales and controversy, simultaneously feuding with censors, the United States government and police all over the country. It didn’t stop groups like N.W.A. from dominating the charts. In the sneaker world, Michael Jordan was well on his way to his first NBA Championship and had already established his line as the hottest, must-have sneaker every single year.

In May of 1990, Sports Illustrated released its infamous “Your Sneakers or Your Life” cover, in response to the many sneaker-related deaths in the months and years leading up to the issue’s publication. Rick Telander’s cover story, “Senseless,” outlined the dangerous issues surrounding the rise in sneaker culture, specifically outlining the death of 15-year-old Michael Eugene Thomas, who died over his pair of Jordan Vs.

The main thread throughout the story and the various crimes was the connection between the drug dealers in different parts of the country and their affinity for, not just sneakers, but all types of athletic apparel—everything from baseball caps, to Starter jackets, to Air Jordans—and the fatal lengths they would go to secure them. Some store owners refused to sell to anyone they perceived to be a drug dealer, not wanting their dirty money, while others opened their arms to the young dealers who flaunted their cash and spent it with reckless abandon.

With the sneaker industry under heavy scrutiny and anything perceived to be connected with the hip-hop community becoming a major red flag, sneaker endorsement opportunities for rappers began to dry up. “I’d rather eliminate the product than know drug dealers are providing the funds that pay me,” said Jordan in response to the Sports Illustrated article.

Even with rap about to embark on what some might deem its golden era, with the debuts of (then-better-known-as-) Snoop Doggy Dogg, Wu-Tang Clan, Notorious B.I.G., Tupac Shakur, Nas and A Tribe Called Quest on the horizon, there is a noticeable absence of sneaker-rapper collaborations during this time. It’s hard not to think that, on some level, there was a conscious decision by corporations to distance themselves from the hip-hop community. Given that acts like Public Enemy had become...well public enemies...to uptight conservative “family values” advocates throughout the 1980s, it doesn’t take a leap of faith to see why—at the time—businesses weren’t willing to stake their reputations on the burgeoning musical genre.

But just because there were less commercials and endorsements permeating the media, it doesn’t mean that hip-hop’s influence in sneaker culture was dwindling.

In 1991, DJ/NYC legend/Rock Steady Crew member/sneakerhead Bobbito Garcia penned a sneaker manifesto for The Source titled, “Confessions of a Sneaker Addict.”

Not only was this an entertaining essay about sneakers in the go-to hip-hop magazine, but Bobbito basically predicted the next 25 years of the sneaker industry, from the rise of exclusive retros to the eventual creation of a full-length Air Max air bubble. It’s an important piece of sneaker culture nestled in the pages of rap’s bible.

“Hands down the dopest kicks ever were Nike Air Force 1 model that came out in ’83,” Garcia wrote. “The second Air Force 1s—which Nike stopped manufacturing for a couple of years and then re-released—have come out in more flavors than your mother’s teeth. The Air Force 1 combines the ruggedest technology and comfort while not sacrificing a subtle sleekness in style.” Air Force 1s were always huge in Philadelphia and New York, aptly dubbed “Uptowns” for their immense popularity in Harlem, and they’ve had a relationship with hip-hop over its 35-year history unlike any other shoe in the market, which Garcia explained perfectly.

By 1992, rap infiltrated college basketball thanks to Michigan’s Fab Five, the five freshmen led by Chris Webber, Jalen Rose and Juwan Howard who took the country by storm and led the Wolverines to the National Championship game two years in a row. Their style—black sneakers, socks and baggy shorts—combined with their collective swagger, culminated in an aesthetic presence clearly influenced by the rappers of their day. Now, 25 years later, rappers like Wale still mention the Fab Five as style influences.

Chapter 3: The Takeover (1996-2003)
“Check ‘em out it’s the new A5’s, ya gotta rock ‘em/they even put a zone in the league to try to stop him…” - Jadakiss

As the decade started to wind down, two key things were happening that affected the future of rap and sneakers. Rap’s influence had become undeniable across the board. Rap dominated the pop music landscape and as rappers became more successful, they began to diversify their portfolios. Puff Daddy (Sean John), Jay-Z (RocaWear) and scores of others launched their own clothing lines. The endorsements started to return as they muscled their way into the fashion world. In 1999, LL Cool J wore a FUBU hat and name dropped the brand in a GAP commercial, giving the brand visibility with no advertising investment. Given that those who wore FUBU were unlikely to find themselves filling up their wardrobes with staples from GAP (and especially vice-versa) this crossover cosign signals a major sea change in hip-hop’s influence on the wider apparel market. Rap became big business in a way it never had before and the sneaker world was ready to cash in once again.

Michael Jordan, who still had the most popular sneakers in the world, was nearing retirement. This left an opening, not just for sales, but for influence. There were plenty of great players in the league, most of them already under the Nike umbrella, but there was one young player whose skill, attitude and style was best suited to usher in the hip-hop era: Allen Iverson.

If there was one athlete who was ever the perfect vessel to transport rap culture to the sports world, it was Iverson. He was the anti-Jordan who favored du-rags and throwbacks to suits and ties. He spoke his mind instead of carefully curated PR message points. He was authentic and the hip-hop community gravitated to him, and vice-versa. At a time when the genre was reaching new heights, Iverson was the perfect ally in the sports world to bring rap back to the forefront of sneaker culture. Years after his playing days were done, he even name-dropped rappers in his Hall of Fame speech.

Iverson achieved success immediately upon entering the league, and his Question line with Reebok took off. Reebok would go on to give him a lifetime contract.

In 2001, in the midst of an MVP season with the Philadelphia 76ers, Iverson released his new A5 sneaker. The commercial would feature an original track produced by The Trackmasters and starred Jadakiss. The commercial and the sneaker was a huge success, propelled by Iverson’s stellar on-court play and a killer advertising plan. The three would reunite the following year for the A6 with Jadakiss and Iverson trading bars over another Trackmasters beat.

Iverson’s enormous success opened the floodgates for companies to once again take chances on rappers as high-level endorsers. The investment by Reebok in Iverson, someone so closely associated with the rap community, cannot be overstated.

In 2002, at the peak of his success, Nelly released “Air Force Ones,” an ode to his crew’s favorite kicks. The video features hundreds of pairs of Air Forces in every color imaginable, typically with a matching jersey and hat to go with it. Some may have viewed “Air Force Ones” as over-the-top product placement, but Nike sure didn’t mind the free advertisement. It was, without a doubt, an entertaining tribute. “Nothing get the hype on first sight, like white on whites,” Nelly rapped. He was right.

This era saw the return of sneaker collaborations with rappers and increased visibility in ads, but in 2003, two of the biggest names in rap inked deals that would change rap’s relationship with sneaker culture forever.

Jay-Z and 50 Cent signed endorsement deals with Reebok in 2003 that included signature shoes for each respective line and a commercial featuring the two of them rapping over a Just Blaze beat. Again, Reebok was taking a chance and thinking outside the box. The same company that achieved so much success going against the grain with Iverson seven years earlier, signed two of the biggest rappers in the world in an effort to compete with the other shoe brands who were focusing solely on athletes. Reebok and FootLocker would go on to sponsor their co-headlining “Rock the Mic” tour that summer. “This is part of our strategy to align the brand with athletes, artists and events that reflect youth culture,” said Mickey Pant, Reebok’s chief marketing officer at the time.

50 Cent’s “G-Unit by RBK” line was a hit at a time when 50 was white hot. When he rapped, “I can’t believe Reebok did a deal with a psycho,” on G-Unit’s “Stunt 101,” he sounded like he meant it. Jay’s “S. Carter” shoe was an instant success, selling out in hours upon its release. He showed sneaker companies that you can put a signature shoe on a rapper and have it succeed in the marketplace. Sneakers weren’t just reserved for basketball players anymore. Jay would venture into clothes, vodka and other endeavors over his career, but his Reebok deal would be a game-changer.

Reebok would go on to enlist many other artists like Lupe Fiasco, Paul Wall and Daddy Yankee to the RBK line, but none of them could capture the magic of Jay and 50’s initial run. The landmark deal set the stage for future endorsement deals to come, and proved to the entire industry that—given the right design and the right person, a rapper could carry a successful signature shoe.

Chapter 4: The New Tastemakers (2004-Present)
“Hold up, I ain’t trying to stunt man, but the Yeezy jumped over the Jumpman…” - Kanye West

After the success of Jay-Z and 50 Cent’s Reebok deals, you started to see many more rapper/sneaker company joint ventures throughout the rest of the decade. Companies like Lugz tapped Birdman for a signature line, Wu-Tang linked up with Fila, Questlove designed his own Air Force 1—and that’s just the tip of the iceberg. Rap was officially at the forefront of sneaker culture operating in a post-Jordan world and every sneaker company wanted a piece.

Some were taking it a step beyond one-off collaborations. In 2005, Pharrell paired up with Nigo to create both Billionaire Boys Club and Ice Cream. With the help of Reebok (again), Ice Cream sneakers hit the market in a wild variety of colors and styles. By 2011, Reebok Classics brought on Swizz Beatz to be its creative director.

While this was happening, Kanye West’s star was rising. His classic debut album, “The College Dropout” got its own Bapesta, signaling West’s foray into the sneaker world. In 2009, he would link with Louis Vuitton for a collection of sneakers including the “Louis Vuitton Don” and the “Jaspers.” It would help set the stage for the next great rapper breakthrough in the sneaker industry.

With his design pursuits beginning to rival his musical prowess, Kanye West convinced Nike in 2009 to give him his own signature shoe. This was monumental. It was the first time Nike had ever given a rapper—or any non-athlete for that matter—a signature shoe before. The first iteration of the Nike Air Yeezy was designed by West and Nike Creative Director Mark Smith. Taking design cues from the Nike Tech Challenge II, Jordan III and IV, the Air Yeezy was an instant smash and sold out in all three colorways immediately.

In 2012, the successes kept coming when Nike released the Air Yeezy II in two colorways and again, they sold out instantly. The union wouldn't last long, however. As West yearned for more support and freedom to create, he butted heads with the higher ups at Nike. This creative control conflict would ultimately lead to the end of West’s relationship with Nike in 2013; that said, The Swoosh would sneakily release the much-hyped “Red October” Yeezy II at the end of 2014—getting the unofficial “last laugh” in its Kanye West cycle. In February 2015, Kanye released his first shoe with adidas, the Yeezy Boost 750.

The revolutionary detail about West’s deal with adidas is that it gave the rapper the wider freedom to create his own line, something Nike was unwilling to concede. Every single shoe released by the line in the last two years has sold successfully, and it’s hard to deny West’s expansive influence in the realm of streetwear and sneakers. Along with Pharrell, who also sports a wildly successful adidas line, rappers have genuinely surpassed athletes in the eyes of consumers for determining what’s cool and what isn’t. Looking at adidas’ success with connecting its product with the influence and aesthetics of musicians and celebrities, it’s not hard to see why Under Armour brought in A$AP Rocky for a multi-dimensional partnership in 2017. It’s a move that—as Under Armour explains it—promises to “empower him and his numerous talents to explore new product avenues,” according to Under Armour SVP of Global Entertainment and Partnerships, Todd Montesano.

In November and December, Nike released five variations of the iconic Air Force 1 for its 35-year anniversary. The shoe has played such a part in the rap world over the years, so it’s only right that four of the five designers tasked with remaking the shoe have ties to the rap and entertainment world.

Kareem “Biggs” Burke, one of the founding fathers of Roc-a-Fella Records—who famously purchased 150-200 pairs of Air Force 1s at a time during the Roc’s heyday—re-released the Roc-a-Fella Air Force 1 with the classic Roc logo on the tongue and heel. Travis Scott gave his spin on the design with a detachable swoosh and tan sole. Two of the hottest names in fashion right now, Virgil Abloh and Don C, two creatives who built their names working within Kanye’s inner circle, did their own takes on the silhouette as well.

When tasked with reintroducing its classic sneaker to the world and celebrating its proud legacy, Nike once again called upon the rap world to bring something fresh and create buzz amongst consumers. Considering rap’s impact and influence on the sneaker community, it’s only right.

Conclusion: I’m a Business, Man
”Since I came in the door, became one of y'all leaders/In a fresh pair of Air Force 1 sneakers” - Rakim

Without question, rappers and those closely associated with hip-hop culture dictate what sells and what doesn’t in the sneaker industry today. They are genuine tastemakers whose style choices dictate major trends and influence bottom lines. Rappers always reflected the style of their respective neighborhoods and they made a lot of money enticing their audiences to buy the brands they owned or endorsed in the late-1990s and early-2000s, but now they are influencing on a global scale and all brands are taking notice.

Drake, Kanye West, Pharrell and others yield results. They build anticipation, fuel hype and drive business. While some may not actually take part in the creative process, simply the illusion of their affiliation is crucial.

Growing up, so many of these young men and women who run rap looked at sneakers as prestige products. They saw MJ in his Air Jordans or neighborhood hustlers in Air Force 1s and saw a status symbol. After spending so much time grinding to buy the sneakers they couldn’t afford growing up, the paradigm has shifted in more ways than one; now there are thousands of kids in neighborhoods across the financial spectrum all over the world lining up every weekend to get a pair of sneakers their favorite rapper had a hand in designing.

For years, brands looked to cash in at opportune moments. Whether it was Run-DMC’s ascension or Jay-Z’s time at the top, sneaker companies looked to ride the rap wave when it was convenient. They looked to rappers to appeal to a younger demographic, all the while keeping them at bay, never truly allowing them to infiltrate a world consistently dominated by athletes until it became unavoidable. Now, signing a rapper to an endorsement deal or investing in a partnership with a rapper isn’t a shot in the dark or a leap of faith, it’s damn near a necessity.