12 of the Best Boxing Moments in Hip-Hop History
Hip-hop may be a cultural celebration of the life and times of rappers and a microscope on their trials, tribulations, hopes and dreams, but at its rawest, it is a blood-sport with no room for mercy. Similar to boxing, hip-hop is all about out-scrapping and outlasting your opponent, which is why it's no surprise that hip-hop's history and connection to boxing runs deep and back to the earliest days of the culture.
Before a rap record was ever cut, Muhammad Ali wowed fans and pummeled opponents, doubters, and critics with his verbal brand of pugilism, stringing together short couplets to entertain and infuriate fans before and after his bouts. Often credited as an influential figure in the history of rap, more than a few of hip-hop's biggest names and pioneers have sung Ali's praises in terms of being an MC.
Boxing and boxers have influenced hip-hop, but the same can be said the other way around. During his rise to the top of the heavyweight division in the 1980s, Mike Tyson was one of the first boxers to fully embed himself in hip-hop culture, appearing in music videos by his favorite artists and even using their tracks as motivational music and his soundtrack while walking out to the ring. And on special occasions, rappers have attempted to mimic or take on the role of boxers, and boxers have done the same, putting down the gloves to pick up the mic or show off their lyrical prowess.
Soulja Boy and Chris Brown are the most recent hip-hop acts to talk about stepping into the ring. We've highlighted unforgettable instances where the worlds of hip-hop and boxing collided.
Coming off of his 1989 album release, Walking with a Panther, which many of his fans and critics deemed an underwhelming effort, LL Cool J sought advice from his grandmother, who, in turn, told him to "knock them out." And that's exactly what LL did, resulting in the inspiration for the title of his fourth studio album, Momma Said Knock You Out. Released in 1990, the album and this classic music video, which sees LL preparing to put his critics and naysayers down for the count, is one of the most memorable boxing-related moments in hip-hop history.
Ironically, Canibus' music video for his LL Cool J diss, "Second Round KO," which dropped in 1998, also came with a boxing angle. Mike Tyson appeared in the clip alongside the scrappy lyricist. While Canibus would ultimately lose his battle with L in the realm of popular opinion, this music video and track will always be in the conversation when mentioning boxing and hip-hop.
In 1989, DJ Jazzy Jeff & The Fresh Prince unleashed And In This Corner..., their third studio album as a group, with a lead-single that perfectly captured the times, but was a bit delusional in nature. That song, titled "I Think I Can Beat Mike Tyson," sees The Fresh Prince fantasizing about going toe-to-toe with the then undefeated heavyweight champ. However, Buster Douglas would in fact beat Mike Tyson in a fight just months after the song's release. Some may call it a jinx, but we'll chalk it up as one of the greatest boxing moments to date.
On May 3, 2014, Floyd Mayweather, who has had more than a few hip-hop related moments, made major waves when rapper Lil Wayne walked out with him and accompanied him to the ring prior to his fight against Marcos Maidana. Lil Wayne was with The Money Team member Justin Bieber and gave a live performance of his new Drake assisted single "Believe Me," making the event even more monumental. It's one of the most unforgettable moments where the two blood-sports coexisted.
Roy Jones Jr. was on top of his game in the early aughts and not just as a boxer, but also as an aspiring rapper. The champ managed to marry his love for rhyme, his boxing pedigree, and his business pursuits with the formation of his own record label, Body Head Entertainment and releasing his own rap single, titled "Y'all Must've Forgot," from his debut album Round One: The Album, in 2001. The song, which featured Roy Jones Jr. in his natural element, training, was a marginal hit and garnered him respect in the hip-hop community, and stands as the most renowned rap song from a boxer of all-time.
Shyne may have been under immense pressure and fighting for his freedom after being charged with attempted murder following his now infamous 1999 club shooting, but the Bad Boy rep channeled that energy into his self-titled debut. "That's Gangsta," the third single released from the album, took Shyne back to his Brooklyn roots. The track featured cameos from boxer and Brownsville, Brooklyn rep Zab Judah, who would go on to appear in various music videos from rap's elite.
On Oct. 17, 2000, Talib Kweli and producer Hi-Tek released their collaborative debut album, Train of Thought, under the name Reflection Eternal. While the album was highly anticipated among underground heads and featured spellbinding raps on the part of both Kweli and Hi-Tek, one of the more pleasant surprises from Train of Thought was heavyweight champ Lennox Lewis appearing on the track "Down for the Count." While Lewis' contribution was only a brief skit, it was another sign of rap's connection to the world of pugilism.
There are few boxers as connected to hip-hop as former champ Winky Wright, who at his peak was closely affiliated with the biggest stars in rap, including Dame Dash and Roc-A-Fella's State Property clique. But aside from appearing in the State Property 2 film, one of Winky's biggest rap-related moments was his Reebok commercial with 50 Cent. Released in 2005, the clip sees Winky sparring with 50. This was another instance of boxing's allegiance to hip-hop.
During hip-hop's hostile takeover of the mainstream music industry and pop culture as a whole, many of rap's biggest moguls continued to branch out into other avenues. In 2004, Chris Gotti, brother of Murder Inc. Records founder Irv Gotti, began managing Curtis Stevens, who has since gone on to become a regional NABF middleweight champion. The following year, in January of 2005, Damon Dash also announced that he was entering the world of boxing through a partnership with high-powered promoter Lou DiBella to form Dash DiBella promotions. Those moves would truly cement rap's marriage with boxing.
The idea of rappers taking their beef to the ring may have been reignited with the spat between Soulja Boy and R&B singer Chris Brown. The concept is one that has actually happened before, albeit a few decades ago. On March 24, 1992, Willie D of the Geto Boys and rap pioneer Melle Mel faced off in a celebrity boxing match. The Texan defeated the New Yorker with a vicious knockout in one of the more infamous, yet slept-on, moments when boxing and rap collided.
The Florida rapper, whose no stranger to fighting words, walked out pro boxer Adrien Broner for his fight versus Adrian Granados while performing his latest song "Tunnel Vision."
The Queen Bee made history in more ways than one when she walked out undefeated WBC champion Deontay Wilder on March 3, 2018. Holding court in her hometown Brooklyn's Barclays Center, Lil Kim became the first notable female MC to escort a boxer into the ring. She also bucked conventions by debuting a brand new song, "Spicy," which features Fabolous. Wilder teased the epic cameo before the fight in an interview with XXL:
We've got something good coming up this time as well. Something that—if it goes through—has never been done before. So I'm looking forward to coming out with this particular artist.