This Sunday, Kobe Bryant will play in the final All-Star game of his career. Though he has yet to comment on what he'll do after the season ends, the poetic essay Bryant penned to announce his retirement may hint at a possible second attempt at a previous passion of his: making rap music.  Bryant is just one of many professional basketball players to have tried his hand at freestyling. Since the 1990s, when rap — and later hip hop — breached into the mainstream culture, several NBA All-Stars from Kobe Bryant and Allen Iverson, to Shaquille O’Neal and Ron Artest (a.k.a Metta World Peace) have dabbled in rap music.

The connection between rap and basketball is strongly rooted in similarities within the two cultures. Both are dominated by African Americans, and in a community disproportionately plagued by poverty, both professions are often idealized as a route to a more prosperous future. In a sport rife with trash-talking, NBA players need to have a thick skin in order to succeed. The same is true for rappers, who must survive in an industry notorious for its feuds and rivalries. (See: Drake vs. Meek Mill, Azealia Banks vs. Iggy Azalea, and most famously, Biggie vs. Tupac.)

Allen Iverson is most widely credited with bringing the hip hop culture to the NBA. The 11-time All-Star was one of the first NBA players to proudly attire himself with tattoos, baggy clothes, cornrows, and massive amounts of bling. In the Showtime documentary Iverson, ESPN reporter Scoop Jackson anointed the 2001 Most Valuable Player as “the true representative of what hip hop stands for and is about.” In 2000, during his tenure with the Philadelphia 76ers, Iverson recorded a rap single titled "40 Bars." The track was met with criticism for including violent, misogynistic and homophobic lyrics, and in response to the pleas of activist groups and then-NBA Commissioner David Stern, Iverson was forced to rewrite the song. Due in large part to this criticism, Iverson’s attempt at a music career ultimately never saw the light of day.

One of the greatest centers in NBA history, Shaquille O’Neal is also one of the few professional basketball players to successfully cross over into hip hop. Over his 19-year NBA career, O’Neal amassed four championships, 15 All-Star selections, three championship Most Valuable Player awards, and a regular season MVP award. Off the court, O’Neal has pursued careers in acting, business, video games, law enforcement, and education; however, his rap career was one of his most notable ventures. O’Neal released four studio albums, with his debut album ”Shaq Diesel” achieving platinum status. His most popular single “(I Know I Got) Skillz” peaked at number 3 on the Billboard Hot Rap Songs chart in 1993.

Unfortunately, unlike that of his former Lakers teammate, Kobe Bryant’s rap career wasn’t nearly as extensive. Prior to releasing his own record, Bryant frequently appeared as a featured artist on songs like Brian McKnight’s “Hold Me”, O’Neal’s "3 X's Dope”, and Destiny’s Child's remix of "Say My Name." However, when "K.O.B.E." — Bryant's debut single featuring supermodel Tyra Banks — was released in 2000, it was panned by critics for being gimmicky and inauthentic. The 18-time All-Star was forced to forgo his debut album Visions, and was subsequently dropped from his label.

In an interview with ESPN’s Sam Alipour in 2014, rapper Lil Wayne stated that “athletes wanna be rappers, rappers wanna be athletes," and increasingly it isn't just NBA players crossing over into hip hop.  Artists like Usher, Nelly and Jay-Z have acquired stakes in NBA teams, and in the process expanded hip hop's influence on the sport. In 2013 Canadian rapper Drake was named the global ambassador for the Toronto Raptors. Similar to Jay-Z, who as partial team owner of the Brooklyn Nets was instrumental in the team's rebranding, Drake has played a key role in the rebranding of the Raptors. In August, the team revealed new game jerseys, and the ensemble included an alternate gold jersey inspired by the rapper's music label, OVO Sound. The Toronto franchise has also honored their “hometown hero” with Drake Night the last three seasons. 

This week during the NBA All-Star weekend events in Toronto, Drake will serve as one of the coaches during Friday night's celebrity basketball game. Should he and Bryant cross paths, it may be an opportunity for Bryant to get some pointers from Drake on his next potential career move.