14 Big, Bad & Delightfully Weird Ads From Hip-Hop's 50 Years on Earth

Summer 2023 marks the 50th anniversary of hip-hop’s birth in the Bronx, N.Y.—and this year, major corporations like Google and Amazon are putting up big money to celebrate.

Five decades after pioneers like DJ Kool Herc started experimenting with turntables at local dance parties, hip-hop has grown to become one of the biggest driving forces—if not the primary engine—of the contemporary music zeitgeist. Its influence is everywhere in pop culture, and has been for ages, officially overtaking other genres in the U.S. by consumption in 2017, inflecting and cross-pollinating with every style under the sun, and spawning countless hits, subgenres, stars and crossovers—not to mention, inevitably, tons of brand deals.

In honor of hip-hop’s distinctive roots, its incredible proliferation, and its myriad facets, here are 14 snapshots capturing key moments in its history with corporate America’s marketing machine.

Adidas and Run DMC – 1986

A defining moment for hip-hop and pop culture broadly, wherein the rap group and their savvy business representatives leveraged Run DMC’s genuine love of Adidas sneakers (see: “My Adidas”) into a major and recurring product-and-marketing partnership with the brand. (A 2014 study also found it to be the most popular music ad of all time). 

St Ides feat. Notorious B.I.G. – 1995

Among the earliest brands to hitch its wagon to hip-hop, malt liquor company St. Ides featured a number of West Coast and East Coast rappers in commercials throughout the late ’80s and ’90s, including this classic starring Biggie. (While the brand’s marketing run was relatively short-lived—and controversial—it arguably laid the groundwork for future moments like Jay-Z’s 2003 high-life number for Heineken and Kanye West’s 2010 bit for Absolut Vodka).

Sprite ‘Five Deadly Venoms’ Campaign – 1999

Sprite’s deep history with hip-hop actually dates back to 1986, when it hired Kurtis Blow to pitch its lagging lemon-lime soda to Black youth in one of the earliest national TV ads featuring a rapper. That led to a string of ads in the ’90s featuring HeavyD, KidNPlay, A Tribe Called Quest and Missy Elliot—and, later, the likes of Drake. The association persists to this day, with Coi Leray starring in a 2022 global marketing push from the brand. But this 1999 Kung Fu-themed campaign—featuring Eve, Angie Martinez, Mia X, Amil, and Roxanne Shante battling a villainous Kool Keith—stands out for a mix of reasons, including its relatively rare focus on women MCs, and as a sequel of sorts to Sprite’s 1998 Voltron-themed ensemble effort (which saw Goodie Mob, Fat Joe, Common, Mack 10, and Afrika Bambaataa join forces to defeat an alien invader). The “Five Deadly Venoms” ad, though, resulted in a lawsuit against the brand from the Deadly Venoms—a separate group of women MCs operating as part of the Wu Tang extended family. 

Gap feat. LL Cool J – 1999

LL Cool J’s energetic a-capella freestyle for Gap still feels raw and fresh almost a quarter of a century after its airing—a rare feat for any ad. That might have something to do with a bit of subterfuge on his part. The artist’s cap repped a then-little known Black-owned streetwear brand named FUBU, and his lyrics referenced the acronym’s titular phrase, “for us by us, on the low.” As FUBU founder and Shark Tank investor Daymond John recounts it, Gap didn’t catch wind of the gambit until after the ad started airing and kids began showing up at its stores asking for FUBU caps. But it ultimately worked to the extraordinary benefit of all parties—in what John describes as “probably history’s biggest advertising coup.”

Boost Mobile feat. Kanye West, Ludacris, The Game – 2004

This iconic ad, the “Boost Mobile Anthem,” tapped three of its moment’s top talents—Kanye West representing Chicago, Ludacris representing Atlanta, and The Game representing Compton—to generate one of the best original songs to ever come out of a commercial, period. Sadly, it was never widely released as a standalone track. (But in related hip-hop history, the ad also proved far less controversial than Pepsi’s notable 2002 joint starring Luda, which found the soda giant backpedaling in the face of a thinly-veiled racist backlash from now-disgraced Fox News host Bill O’Reilly and his pearl-clutching minions). 

HP feat. Jay Z – 2006

A deft illustration of Hov’s famous line, “I’m not a businessman—I’m a business, man,” this number from the computing giant featured Jay-Z narrating how he uses his HP laptop to manage his many ventures (all without showing his face—part of the multi-celebrity campaign’s broader gimmick). It inspired another great lyrical quip about the brand “spendin’ 10 million in media on my hands.” (Another icon featured in the same campaign: Pharrell Williams). 

Vitaminwater feat. 50 Cent – 2007

“I took quarter waters, sold it in bottles for two bucks, then, Coca-Cola came and bought it for billions—what the f*ck?,” says 50 Cent in 2007’s “I Get Money.” The rapper’s relationship with Vitaminwater’s original owner Glaceau began in 2004 when he plugged the product in a Reebok ad. As opposed to a typical endorsement-for-cash deal, the rapper negotiated for a minority equity stake that resulted in this classic tongue-in-cheek ad featuring 50 conducting a symphony playing “In Da Club.” The deal also famously netted him an estimated $100 million when Coca-Cola acquired Glaceau in 2007—and set a new gold standard for rappers in brand deals. 

Nike Skateboarding feat. Ice Cube – 2009

This chill ode to L.A.—set to Ice Cube’s track “It’s a Good Day”—shows celebrated skater Paul Rodriguez cruising past the city’s vistas and icons (shout out Kobe Bryant), while flouting the cops and exuding a vibe of effortless cool. It’s a standout example of Nike’s own hip-hop investments—other classics include its Jordan brand’s 2001 video for Mos Def’s “Umi Says” and Rick Ross’ very of-the-moment iced-out 2010 spot—and includes to an amusing cameo from Ice Cube himself, with no small measure of mean-mugging nostalgia.

Chrysler feat. Eminem – 2011

Leaning on the riff from the 2002 hit “Lose Yourself,” this epic Super Bowl ad used Eminem’s Motor City credentials to introduce the Chrysler 200 with the tagline “Imported from Detroit.”

Lucky Charms feat. Biz Markie – 2015

In a less epic, more endearing example, this quirky psychedelic reworking of the late great Biz Markie’s 1989 classic “Just a Friend” (which interpolates Freddie Scott’s 1968 song “(You) Got What I Need”) finds Biz informing viewers of their chance to win a box of all-marshmallow Lucky Charms (because who wouldn’t want that). It’s a comedic bit, on brand with his playful career and enduring reputation as the “clown prince of hip-hop.”

Apple feat. Drake – 2016

With hits like “One Dance”—2016’s official song of the summer, per Billboard—and his 6x platinum album Views, this was one of Drake’s biggest years. This ad from Apple saw the artist use his platform as one of hip-hop’s towering contemporary stars to cut off his own music and instead pump iron to Taylor Swift (enjoying her own moment as one of the world’s biggest pop stars). Overall, a fun sendup of rap bravado and a charming time capsule of some of 2016’s cultural priorities. 

Pepsi feat. Cardi B – 2019

Pepsi is arguably the biggest name in pop music branding. Over the years this has included collabs with rappers—in addition to the aborted Ludacris campaign, there was its 2005 ad featuring Late Registration-era Kanye West, and its 2012 spot leaning into the bubblegum dance pop side of Nikki Minaj’s aesthetic (as opposed to her rapping chops), and its 2021 pop-R&B remake of Grease starring Doja Cat. The brand’s 2019 Super Bowl ad, though, starring Steve Carell, Lil Jon and Cardi B, leveraged the latter’s show-stealing personality and Latin trap chart-topper “I Like It” right on cue with a new era of visibility and commercial dominance from women rappers.

McDonald’s feat. Travis Scott – 2020

While MC Hammer might’ve paved the way with his 1991 parachute pants stunt for Taco Bell, Travis Scott’s 2020 deal with the Golden Arches is notable for its scale of integration. It featured not only a Scott-branded meal (including a Sprite) but also merchandise like a $98 body pillow and a $128 work jacket. All that helped Scott earn a reported $20 million, per Forbes—also just a fraction of his end from various corporate collabs. It was also fortuitously timed for McDonald’s, arguably catching Scott at the apex of his moment—a year before the high-profile and controversial Astroworld tragedy tarnished his popular image.

Uber One feat. Diddy – 2023

This year’s Super Bowl was a big one for meta hip-hop ads. There was Snoop Dogg riffing on being Snoop Dogg for Skechers (with a cameo from bestie Martha Stewart, part of their ongoing bit-meets-genuine-friendship). There was Doritos inspiring relative newcomer Jack Harlow to quit rapping and play a (chip-shaped) triangle, against the advice of Missy Elliott, and only to be shown up by Elton John. But perhaps the most apt demonstration of the long-reified bond between hip-hop and pop music came from Uber One’s spot, wherein mainstay mogul P. Diddy anchors a historical survey of varied hit records—also starring Montell Jordan, Donna Lewis, Kelis and Haddaway—in search of an appropriate musical promo for the ridesharing app. The upshot? Commercial performance is king, regardless of genre—but good taste always comes before the bag.