For three weeks during the summer of 1998, Kobe Bryant lived in the New Jersey mansion of hip-hop record executive Steve Stoute. Bryant was there to try on the role of rap star, but since he was also training to be the next Michael Jordan, basketball consumed most of his time. Every morning, he’d drive to nearby Ramapo College and shoot 2,000 jump shots. Sometimes, Stoute would shuttle in streetball players from New York to help Bryant brush up on his defense. By sundown every day, though, he was tasked with absorbing “the lifestyle,” a kind of initiation into the late-’90s world of rap royalty.

That was the idea, anyway. At the time, Stoute was president of urban music for Sony Entertainment, and he’d recently signed Bryant and his group CHEIZAW to the label. He’d moved Bryant from Los Angeles to New York that summer to, Stoute says, be around the gilded hip-hop industry. Stoute, a marketing whiz and big-picture specialist, was reaching unseen heights in the industry, having recently orchestrated Will Smith’s comeback rap album, the nine-times platinum Big Willie Style. He thought he could do the same for Kobe Bryant. Basketball came naturally to the 20-year-old. Hip-hop was going to take some work.

But Bryant was up for it. When he wasn’t playing ball, he was recording at the Hit Factory with late-’90s producers par excellence the Trackmasters and their stable of artists, which included Nas, Noreaga, Punch and Words, Nature, and a young scrapper named 50 Cent. Bryant lived it up in New York. He routinely went clubbing with Stoute and dined at Mr. Chow, the Chinese restaurant favored by the nouveau riche.

None of that impressed him, though. Bryant was in love with the purest form of hip-hop, and he wanted a challenge: to battle the pros.

He got his wish one night at the Hit Factory, when he teamed with CHEIZAW member Broady Boy to take on Punch and Words. Bryant, typically unflappable, maintained his composure at the outset. Upon entering the fray, he rapped: “I quantum leap into the future and battle myself.” After a few rounds, Broady ran out of lyrics and the sparring session wound down. Kobe then chided his teammate. “Yo, you got to be in lyrical fitness, man,” Bryant told Broady, referencing a well-known lyric by the rapper Canibus.

“You could tell he was influenced by Canibus,” says Words, citing the snarling MC who was then the standard-bearer in battle rap. “Kobe had a quality of lyrics. When he got into the cipher, you didn’t look at him as just Kobe. You looked at him as a dude that could rhyme and if you sleep on him, you could get embarrassed.”

Blessed with talent and a maniacal drive to succeed, a rap career would seem a manageable goal. So why did Kobe Bryant fail as a rapper?

By the time Bryant’s pursuit began, the trend of athletes moonlighting as musicians was losing its novelty. Shaquille O’Neal had a surprisingly competent verse on FU-Schnickens’ 1993 hit “What’s Up Doc? (Can We Rock?)” and followed it up with a platinum album (1993’s Shaq Diesel) and a gold album (1994’s Shaq-Fu: Da Return). But his latest, 1996’s You Can’t Stop the Reign, peaked at 82 on the Billboard 200, signaling a slowing market.

There were other signs. The compilation album B-Ball’s Best Kept Secret, released in November 1994, featured songs from Gary Payton, Jason Kidd, and Cedric Ceballos. It lives on as the centerpiece of most “worst rapping athlete” listicles. The following month, Deion Sanders’s Prime Time debuted at 70 on Billboard’s Top R&B/Hip-Hop Albums chart.

Bryant’s foray into hip-hop would be just as disastrous. After his pseudo-rap fantasy camp in New York ended, he recorded intermittently. A spring 2000 release date was set for Visions, his debut album. But after the first single stalled, the album was never released. By the end of 2000, Sony had dropped Bryant from the label. Kobe Bryant has never revealed what went wrong.

Philadelphia has a rich, oft-overlooked history in hip-hop. Cool C, Three Times Dope, Schoolly D, DJ Cash Money, and, of course, DJ Jazzy Jeff & the Fresh Prince laid the foundation in the ’80s. By the time Bryant was a student at Lower Merion High School in the mid-’90s, Philly’s sound mirrored what was happening just 95 miles north in New York. “All of them were on some lyrical indie hip-hop shit,” says former radio DJ Bobbito Garcia, a 1984 graduate of Lower Merion.

That’s where the similarities end. With the record companies located primarily in New York, the scene was still very much based on networking and nebulous connections — a cousin who knew someone in Russell Simmons’s office or a friend of a friend interning at Bad Boy. Artists strove to get their demos into the right hands. Meanwhile in Philly, rappers on the cusp won exposure and credibility in a more traditional way: They battled.

Bryant was born in Philadelphia but moved when he was 6 years old, after his father Joe “Jellybean” Bryant signed with a professional basketball team in the central Italian city of Rieti. When Bryant returned to Philly at the age of 14, he met Anthony Bannister, a 16-year-old working at the Jewish community center on City Avenue where Joe Bryant was the fitness director. “Kobe was 14, skinny, wiry but passionate and determined,” Bannister recalls about first meeting Kobe in 1992. They quickly bonded over basketball and beats. At first, Bannister was Bryant’s rap cicerone, providing a crash course on the golden age of hip-hop Bryant had missed while living abroad. Bryant took up rhyming soon after, battling in the Lower Merion lunchroom and pounding out beats for other MCs with a pencil and eraser.

Bryant also befriended the best rapper in school, Kevin “Sandman” Sanchez, who taught him about breath control and enunciation. At the time, Bannister, who knew Sanchez from the scene, was scouting MCs with the intention of forming a group; he fancied himself a RZA-like mastermind. With Bryant and Sanchez already in the fold, Bannister added Broady Boy and Jester. The group drew its name from the Chi Sah gang in the Shaw Brothers kung fu flick The Kid With the Golden Arm; they later altered it to the acronym CHEIZAW.

“I thought we were the best in the city at that time,” Bannister says. “Kobe was nice, man. He was lyrical. I wouldn’t have put him in the group if he wasn’t.”

Bannister, sitting on a bench in Rittenhouse Square on a cold Monday afternoon in early April, is nostalgic about those days. There are too many memories of times with friends now estranged. He remembers one night when the CHEIZAW gang left a show at Gotham, an old club on Delaware Avenue, stopped by Rittenhouse Square, and rhymed all night.

They rapped everywhere together. CHEIZAW battled at South Street, Parkside, Temple University, an underground mall called the Gallery, and Belmont Plateau, which was immortalized in DJ Jazzy Jeff & the Fresh Prince’s “Summertime.” Bryant, who called himself The Eighth Man, often didn’t battle other crews but always rhymed in what Sanchez calls the group’s internal sparring sessions.

Al Price, a Philly MC from the group Black Ops, recalls one such session at Broady’s apartment. “In a room full of hungry underground MCs, he was just another hungry underground MC,” Price says. “Kobe liked to catch you off guard. He liked the competitive part of it. He liked to dig into the beat and flow and mess with rhythms and tone and pitches. You could tell, he wasn’t dope by accident.”

“Kobe was talented,” Sanchez says. “I remember when the movie Solo came out with Mario Van Peebles, Kobe wrote this rhyme about him being a cyborg destroying MCs.”



CHEIZAW soon added the producer Russell Howard, Sanchez’s friend Sai Bey, and, at the behest of Charlie Mack, Will Smith’s former bodyguard who briefly advised the group, a female MC named Akia Stone. Now a budding national celebrity thanks to his dominance at Lower Merion, Bryant announced he was bypassing college to enter the NBA draft. In June 1996, the Charlotte Hornets drafted Bryant with the 13th pick, and then, in one of the most lopsided trades in NBA history, sent his rights to the Los Angeles Lakers for Vlade Divac. Everyone in CHEIZAW had big plans and Kobe was going to be their meal ticket. But things quickly went awry for the group.

It’s impossible to tell the story of Kobe Bryant’s rap career without telling the story of Kevin Sanchez, the man responsible for molding Bryant into an MC.

On July 27, 1996, a man concealing his face with a Stroehmann bread bag robbed the 7-Eleven on City Avenue. The clerk told police the thief was 5-foot-8 and 120 pounds, with dark eyes. Sanchez, who is 6 feet and 185 pounds and green-eyed, says he was at the Jewish community center rhyming with Bryant, Bannister, and others at the time of the crime. Still, the clerk picked him out of a lineup. Sanchez was arrested.

Sanchez remained in contact with Bryant before his September 1998 trial; Bryant helped post his bail, according to Bannister, and appeared at a preliminary hearing. Sometimes, Bryant called him asking for “some energy” before games. Sanchez would then sit in his car and rhyme over the phone to Bryant. “For some dumb reason, I thought I had something to do with him scoring 30,” Sanchez says. “I was silly like that.”

Sanchez’s trial lasted two days. Five eyewitnesses couldn’t identify him, but he was found guilty of armed robbery and sentenced to five to 10 years in prison; Bryant paid for Bannister to fly in from Los Angeles to testify, but Bryant didn’t appear at the trial. After the conviction, a juror told the Philadelphia Daily News that Bryant’s testimony could have swayed the jury. Nearly 15 years later, Sanchez isn’t bitter. “It wasn’t Kobe’s fault I went to jail. I don’t blame him,” he says. “We didn’t think we’d need him. It was a false ID. There was no way we were going to lose.”

Sanchez spent 15 months in prison before a judge granted his request for a new trial. Out on bail, he got his old job back working maintenance at a beauty salon, and had courtside seats waiting for him whenever the Lakers were in town. But the district attorney challenged the appeal and Sanchez returned to prison. He was released in early 2007 after serving five years. He’s still a Lakers fan.

“No one can tell me nothing about my team,” he says. “I ride and die for them.” Kobe Bryant is his favorite player. And whenever he plays roulette in Atlantic City, he always puts his money on number 8 and number 24.



When the group signed with Sony, CHEIZAW consisted of Kobe, Broady Boy, Anthony Bannister (who went by the name Tréoz), Russell Howard, Akia Stone, and Sai Bey; unhappy with the structure of the contract, Jester refused to sign.

Stoute and the Trackmasters signed CHEIZAW shortly after hearing Bryant rhyme one night at a studio session. Jerrod Washington, a former special teams player for the New England Patriots who eventually became his brother-in-law and music manager, brought Bryant to the studio that night. But a group project wasn’t meant to be. “I just felt like, I’m going to sign the group and slowly but surely I’m sure they would all fall out and we would have a Kobe record,” Stoute says. “It’s a natural thing that happens with new success — friends change, things grow apart. L.A. Reid taught me that. L.A. Reid signed Toni Braxton and all her sisters just to sign Toni Braxton.”

With CHEIZAW in Los Angeles and at work on new music, Sony strategized ways to make Bryant a superstar. He rhymed at a concert thrown by the legendary Los Angeles radio duo Sway and Tech and recorded a short verse for a remix of Brian McKnight’s “Hold Me.” He even appeared on a song with his frenemy Shaq-Fu.

That song, which is called “3 X’s Dope,” appears on O’Neal’s 1998 album Respect. It features the female rapper Sonja Blade, who was writing for Shaq at the time, and a third rapper not listed in the credits who kicks off the track. Kobe Bryant is that rapper. Some say Bryant’s name wasn’t listed for label-clearance reasons (Shaq recorded for A&M). Others say the song was meant to be a surprise. It was recorded in early 1998 in Los Angeles with legendary hip-hop producer Clark Kent. At first Bryant sat quietly while Kent finished composing the song. O’Neal kept the mood light, cracking jokes and talking trash to his little bro.

“You got to come with your A-game, son. You got to come with your A-game.”

Bryant didn’t back down.

“Nah, I’m ready, son. I got mines.”

Then he stepped into the booth. Bryant memorized his verse, but he rapped too fast, zooming past the tempo of the production. By the third take he’d nailed it. “When he laid that down, the whole studio erupted because it was like, ‘This guy is not playing.’ This was not A-B-C stuff,” Sonja Blade says, laughing. “I couldn’t listen to his verse for years.”

I recently played Bryant’s verse for Sonja Blade.

“You know what’s funny? He sounds dope,” she says afterward. “Compared to the rappers today, he’s dope. He sounds like an underground backpack rapper. It don’t even sound like Kobe Bryant. I would want to hear more from this kid if I didn’t know who he was. That’s funny. Nobody raps like that anymore. Yo, he came there to prove a point. He put thought into that. I couldn’t hear it for years when everyone joked about it. Now hearing it, he doesn’t sound bad.”

Clark Kent has a different take on Bryant’s performance. “He just seemed like one of those guys that wanted to be good so bad that he was trying to use the most intelligent [words] and have the sick vernacular. It was like, ‘Calm down, duke. Just rap.’ He was the lyrical-miracle-genius-type rapper.”

I played the record again for Clark, too.

“Hilarious. It’s just funny because knowing that we was there and he was rapping was hilarious. He was like this little basketball dude This was his second year [in the NBA] so he was dumb young. He thought he was a rapper.” Kent giggles. “Oh my God, hilarious. I don’t even want to talk about this anymore.”



With Bryant camped out in the studio, Sony continued to emphasize the marketing campaign. The label sought ways to capitalize on his youth, NBA fame, and growing music industry ties — escorting Brandy to his prom and appearing in the Destiny’s Child video for “Bug A Boo.” (To secure his bona fides, Bryant was willing to take on all comers, including Toronto Raptors point guard Alvin Williams at All-Star Weekend.) The crux of the label’s plan, however, was eliminating the group.

The project gradually shifted, from a CHEIZAW album to a Kobe Bryant featuring CHEIZAW album to a Kobe Bryant solo album. Sony also steered Bryant toward a radio-friendly pop sound. Like most battle rappers, notably his hero Canibus, Bryant struggled with the shift. He made odd choices, like attempting to rhyme over “The Imperial March (Darth Vader’s Theme)” from Star Wars. Sean “S-dot” Francis, a producer from Philadelphia, was brought in to provide a sleeker sound. Stoute and Jay-Z were fans of S-dot’s work.

Meanwhile, Anthony Bannister didn’t approve of the changes. He wasn’t a fan of what he calls “Mickey Mouse Club music” and felt Bryant growing distant. One morning in November 1999, the two old friends had breakfast in Santa Monica. Later, while grabbing a pint of Ben & Jerry’s from a grocery store, Bryant pointed to a magazine at the checkout counter.

This is where I’m headed.

Will Smith was on the cover.

Nah, Kob, you’re bigger than that. You bigger than that lyrically, artistically. Don’t go that pop route. Don’t go the Will Smith route. Go with what you know. You know about Lodi Avenue, Parkside Avenue, your grandma is from the hood.

Bannister returned to Philadelphia a few days later.

Visions‘ first single needed to be special. One day in the studio, S-dot played the trumpets from the Sugar Hill Gang’s 1980 single “8th Wonder” on his keyboard. Jerrod Washington quickly jotted down a chorus that matched the melody: “K-O-B-E, I L-O-V-E you / And I think you are very fine / If you give me one chance I promise to love you / And be with you forever more.”



Lenny Nicholson, a Sony A&R at the time, brainstormed an idea to sweeten the song: Tyra Banks. The supermodel, seen above with S-dot, would sing the song’s syrupy hook, an idea the suits at Sony were ecstatic about.

“The marketing and promo people had everyone sold that they were going to make it a no. 1 record,” says former Columbia A&R Rich Nice. “Someone said to me, ‘Yo, it’s going to be great for the video. It’s gonna look fantastic.’ It’s gonna look good, but shit, it’ll still sound crazy.”

The single debuted in January 2000. A performance at All-Star Weekend that month — complete with Bryant in a leopard print hat and leather suit, Lakers jersey–bearing backup dancers, and Tyra warbling the chorus — was a fiasco. The blowback was brutal and the Hype Williams–directed video was banished, never to be seen by the public. “K.O.B.E.” confirmed skeptics’ worst fears: The song was a transparent gimmick, and Kobe Bryant was a novelty rap act. Suddenly, his rap career appeared doomed. “It got to the point where it started getting wack juice on it,” Nice says. “So people [at Sony] started wiping their hands.”

But Bryant was defiant. He retreated to the studio with Broady and returned to his roots: lyrically complex underground rap. That, of course, is not what Sony had in mind, and the album was ultimately scrapped. By that point, Stoute had left the company and Bryant’s champions had all but abandoned him. So Sony did what it would have done to any other rapper bleeding red ink: Kobe Bryant was dropped.

Soon after, Bryant and Washington regrouped, forming their own independent label, Heads High Entertainment. An October 2000 press release stated its mission: “To bring feel good music and uplift [sic] message to the community through their artists’ music.” The roster included Bryant; Broady Boy; Sean Francis; Jerrod Washington’s cousin, a rapper named Rico; a female rapper from New York named Uneek; and Da Babies, a kids act. There was a showcase at the House of Blues in Los Angeles in the summer of 2000, but a proposed “We Are the World”–style charity single tackling school violence never got off the ground. Within a year, the label folded.

Uneek, who’d moved to Los Angeles to record for Heads High, says she learned about the end of the label when she received an eviction notice. “The situation we had was that I got my advance and they would cover my rent and my car note,” she says. “I bumped into Shaq at the club and I told him that I was in a bad situation. Shaq went into his pocket and gave me a few dollars. Shaq knew me from the mixtapes in New York. He was like, ‘You see, you should have signed to my label. We don’t treat our artists like that.'”

Kobe Bryant’s rap career was over, relegated to an unlikely footnote in his extraordinary career, like Michael Jordan’s time with the Birmingham Barons. Through the Lakers media relations department, Bryant declined to be interviewed for this story, as did associates like Washington and Nicholson, who still reside within Bryant’s circle. But it hasn’t been so easy for the aspiring MCs in CHEIZAW to move on with no pro basketball career to fall back on. Broady Boy, who teaches and works as a part-time sound engineer, wrote via text message, “Kobe doesn’t want to discuss [his rap career] right now and I respect that because of the respect he has shown me.” Sanchez is also juggling two gigs, working in a Nestlé factory and, in a cruel coincidence, Bimbo Bakeries, the bread company that owns Stroehmann. He’s still trying to make it in hip-hop. Now known as Tana Da Beast, Sanchez raps alongside Freeway, Reef The Lost Cauze, Jack Frost, and former Roots member Malik B, in the Beard Gang. He says the group is pursuing a deal with Duck Down Music and DJ Premier’s Year Round Records. On January 30, Sanchez tweeted at Bryant, “yo bean this kev sanchez how u been? just dropping a line on u I’m thinking bout moving to La. I got sum music 4 u get at me cuz.”

Bannister, who admits to falling into a depression upon returning from Los Angeles, runs the audio department at a library for the blind. He sometimes sees Kobe when the Lakers come to Philadelphia to play the Sixers. Sometimes during shootaround he’ll shout, “What’s good, Eighth Man?” He says his old friend nods back every time.

Bannister says it’s tough for him to talk about his youth, back when he had big dreams of CHEIZAW taking over the world. But more than anything, he just wants his friend back.

“I miss him,” Bannister says. “He got babies. I got babies. We had so many plans, man. I got three kids. Yup, three beautiful children and a wife who has heard all the stories. ‘Yeah, right. You don’t know Kobe Bryant. You weren’t in L.A. Whatever, Ant, OK.'”

He says he knows Kobe still has a little bit of Lodi and Parkside Avenue left in him. “I know Kob still rhymes now,” he says. “He likes to say he doesn’t, but I know he still rhymes and is still writing. It’s in him.”

Thomas Golianopoulos (@golianopoulos) is a writer living in New York City. He has contributed to the New York Times, Wired, the New York Observer, and Spin.