Artists don’t get off-seasons. And unless you’re Allen “Practice is a State of Mind” Iverson, you usually don’t make the NBA Hall of Fame without spending summers locked in gyms, weight rooms, and hyperbolic elasticity chambers only accessible by staring into a mirror at midnight and chanting “Steve Nash” three times in rapid succession.
In the hip-hop world, originality is synonymous with obsession. The worst-kept secret of most great MCs is that they are usually Thesaurus-obsessed rap nerds, who spend more nights in the studio than at home sleeping on a pile of money surrounded by many beautiful women. See also, Devin the Dude’s “What a Job” or the quantity of rap songs titled “No Days Off.”
This partially explains why the NBA has never produced a transcendent musical talent. Plenty of outstanding athletes have bars and Shaq conjured a handful of classic singles, but none ever inhabited a singular character, personality, or originated a style. In the meantime, I keep a candlelit vigil for Nick Young to start recording freestyles over “Duffle Bag Boy” during timeouts. (Javale & Swaggy is the frontrunner for the 2019 Grammys.)
We can blame the 10,000 hours theory, but also need to assign guilt to David Stern, who reigned over the league with the joyless Puritanism of the minister in Footloose. The ex-commissioner’s threats to Iverson over “40 Bars” created a cloud of censorship that still endures under his successor Adam “Stretch Armstrong” Silver. As the Rick Ross exception attests, you can produce excellent rap music without honesty, but it certainly helps. And no NBA player is about to risk sponsorship deals or suspension to spill the tea about the conflicts, groupies, and frustrations that occur behind closed doors (unless D’Angelo Russell films it).
Nonetheless, rapping NBA players remain one of the most joyous peripheral quirks of the league. Pro ballplayers have recorded songs since Wilt Chamberlain cut “By The River” in 1960, but the onslaught of modern social media and ease of streaming allows us to bypass the fact that none of it is really worth paying for — save maybe for The Best of Shaquille O’ Neal, complete with a bonus “Kobe, tell me how my ass tastes” freestyle cassingle.
With the beckoning of Christmas, a holiday unofficially consecrated to hoops, it’s only fitting to examine the greatest and weirdest moments in NBA rap history.
The Top 10
10. Lou Williams
Consider it Game Theory, but like Jayceon Taylor, Williams has the bad habit of stealing flows from whomever he’s rapping alongside. On his “Ima Boss” freestyle, he sounds like he learned how to rap running wind sprints against Meek Mill. When he conscripts 2 Chainz, Williams’ flow reverts to his native Atlanta drawl. Conversely, it offers Williams a certain versatility that allows him to hold his own against more naturally gifted talents — similarly to how the 6’1, 175 lb. guard has survived in the league for a dozen years despite being built like Lou Bega. In addition, the three-point specialist successfully maintained a polyamorous relationship that inspired Drake to pay tribute on “6 Man.”
9. Cedric Ceballos
Despite pioneering G-Funk and gangsta rap, Los Angeles has largely failed to nurture rapping athletes. The principal exception being ex-Cal-State Fullerton and Lakers star, Cedric Ceballos, whose collaboration with Warren G was a unanimously lauded highlight from the immortal B-Ball’s Best Kept Secret compilation. The video features the blindfold-wearing dunk contest champ surrounded by admirers, balling on the Venice Beach courts, and rapping as well as anyone in the Dove Shack. It’s a slinky minor G-Funk gem whose credibility is only enhanced by Ceballos’ subsequent move to quit the Lakers mid-season and rent a houseboat in Lake Havasu — which my sources tell me partially inspired the plot of the film, Spring Breakers.
8. Allen Iverson
The Big L of rapping ballplayers, Jewels’ career was wrongfully cut short and shrouded by the eternal “what if?” question. During the early 00s, State Property and Major Figgas were the only Philadelphia rappers capable of matching the fury of “40 Bars.” Blessed with an LL Cool J-like boom to his voice, Iverson rapped the way he played: a nimble, ruthless, and relentless salvo. Hip-hop is idea as much as art form, and no NBA player has more holistically embodied its subversive streak and sense of rebellion as much as A.I. It’s never too late for him to diss White Iverson either.
7. Stephen Jackson
Raised in Port Arthur like his spiritual model, Pimp C, Stak5 parlayed an NBA championship resume into a respectable entrée into the rap world. In addition to collaborating with Texas legends Bun B and Killa Kyleon, Jackson recruited Scarface for a pair of songs, including “America Da’ Beautiful.” Recorded in the wake of the Donald Sterling fiasco, it’s the most savage indictment of historic and modern-day institutional racism ever recorded by a professional athlete.
When Tim Duncan asked to appear on his album, Jackson flatly refused without even hearing him rap. As if that wasn’t enough, Jackson proceeded to call every other NBA rapper wack, including Kevin Durant and Iman Shumpert who both appeared on his mixtape. He claimed that he’d eat Allen Iverson’s lunch and said that Shaq had “no swag,” and presumably did it while telling them to smell his $64 cologne.
6. Metta World Peace
Allow me to quote from Prodigy’s My Infamous Life biography: “Ron Artest had become a big-time NBA star for the Chicago Bulls, and when he heard about what I was doing with [my artists] Bars ‘N’Hooks and the Queensbridge movie, he gave me ninety thousand dollars in start-up money to help with the expenses — studio time, records, stickers, travel expenses, Infamous Records chains for Delorean and Bars, and Infamous Records leathers, jerseys, t-shirts, and bandannas to promote the label. Ron-Ron, as we call him, was a real-ass n*gga for looking out like that. To this day, if he asked me for anything I would do it for him.”
Off that alone, Metta World Peace belongs on this list. But then he wrote the songs, “Hennessey at Halftime” “and “Champions.” That’s not even counting making Craig Sager say “Queensbridge” on national television after the Lakers won the title. He also wrote the bizarrely moving, “Afghan Women,” a tribute to the plight of oppressed women in Afghanistan. Tell Sweden to give him the Street Nobel.
5. Iman Shumpert
Let’s examine Shump’s achievements before turning 27: sported the best high top fade since House Party, appeared naked in Kanye’s “Fade” video with wife, Teyana Taylor, created the still relevant #KnicksTape, won an NBA championship, and spit the “Chiraq” freestyle, which goes very hard and is arguably the most legitimately artistic video made by an NBA player. It’s impressive enough to where we don’t even need to deduct points for his appearance on Everyday Struggle.
4. Chris Webber
We’ve seen better producers who could rap and control the maestro, but C. Webb stays in possession of the title of most multi-faceted baller/rapper/beatmaker (and not the other way around). After winning the rebounding crown, the-then Sacramento Kings star recorded 2 Much Drama, a predictably forgettable affair that managed a pair of slappers thanks to cameos from Redman and Kurupt. His career highlight, basketball or otherwise, might be placing two beats on Nas albums. Admittedly, Nas has infamously erratic taste in production, but if you can be behind the boards for one of the five greatest rappers of all-time while averaging 21 and 10 for your career, you are automatically ensured a spot on a completely arbitrary list.
3. Dana Barros
It’s unquestionable that Dana Barros was a better rapper than Benzino. During his years at Boston College, the future 76ers and Celtics point guard already doubled as a rapper and DJ — scratching in his dorm room, cutting four-track tapes, and attempting to sell his mixtapes on the streets and at Newbury Comics. The EPMD-obsessed “breakout star” of B-Ball’s Best Kept Secret could have had a legit minor rap career. His single, “Check It” sounds like a classic long-lost Nine single; while he seemed like a reasonable candidate for the fourth member in Brand Nubian on “Ya Don’t Stop.” In all honesty, they would’ve been better off replacing Lord Jamar with Barros.
2. Damian Lillard
Allow for this most mildly scorching take: Damian Lillard is easily the best NBA rapper since Shaq. If he can manage to balance the workload of being an all-star point guard, enlist the right collaborators, and continue to evolve as an artist, he could potentially match him.
When his #4Bar Friday series started, skepticism prevailed. But his Sway freestyle flashed a surprising introspection and a natural gift to let the beat breathe—darting in and out of the pocket as though he exploited a botched rotation in a zone defense. Never bet against someone raised in Oakland. Nor against a guy who became one of the league’s best and most clutch players despite attending a school in the Big Sky Conference. His official debut Confirmed feels contemporary without feeling wholly derivative; it contains Lil Wayne, 2 Chainz and BJ The Chicago Kid cameos, and comes off as a well constructed, thoughtful and complete full-length — even if it occasionally veers to J Coleicisms. He’s already a Top 5 all-time Portland rapper. No disrespect to Rasheed Wallace.
1. Shaquille O’Neal
No one had better taste, more charisma, or the star wattage to be able to handpick the best collaborators in hip-hop. Who else but Shaq could get Biggie, Rakim, Jay-Z RZA, Method Man, and Mobb Deep to guest on tracks and ghostwrite lyrics? Or DJ Quik to produce “Straight Playin,” the song blaring in every LA lowrider and Jeep throughout the summer of 1997 — while Los Angeles celebrated its good fortune in snatching the Big Aristotle away from the Magic.
If Shaq could be lumbering and stilted on the mic, he compensated with an innate star quality and goofball charm. With “Biological Didn’t Bother,” he penned a mawkish but still moving paean to his stepfather. Nor could any NBA rapper match his commercial appeal, as the Jive artist landed two Top 40 singles, and became the first and only rapping athlete to achieve a platinum plaque. He’s the unquestioned greatest of all-time, even if he never properly responded to Kenny Dennis.
No Chance of Being Included On This List: Kevin Durant
Let us never speak of it again: K.O.B.E.
Kobe rapped like the type of guy who would agree to do this photo shoot.
Too Soon to Call
Lonzo Ball (Zo)
Zo has a legit shot to go down as one of the best rapping athletes of all-time, but he needs to find his own style. You can’t be a big baller until you stop stealing your rapping and shooting technique from Drake. He probably should get Lavar to ghostwrite punchlines for him too.
In A League of His Own: Delonte West
When we look back in the annals of hip-hop history, we’ll realize that the KFC freestyle was the apotheosis of the based freestyle. Neither chicken nor Chipotle will ever be the same.