#2 Allen Iverson
Allen Iverson is the player most recognized to have solidified the connection between basketball and rap music. Iverson aka The Answer aka Jewels was the ultimate hip-hop baller. He fit into every stereotypical image a rapper could ever have. From tattoos to baggy jeans and the plethora of chains, he had it all. He was such an icon in his time that he had one of the largest numbers of jersey sales of all time.
Considering his cultural and other organic ties to hip-hop, Iverson was not a hip-hop genius. He had many issues with homophobia and violence in his lyrics. Honestly, it was even surprising to see that his music would be released given the issues the songs had.
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Unfortunately, these lyrics did have a past. Iverson has had multiple arrests for gun possession and violence. While these issues threatened his basketball career, Iverson was just being himself and nothing else. However, it would be nice to know that there was more to him than this.