Off the court, the only thing greater than LeBron James’ love affair with wine is his obsession with all things hip-hop. With all due respect to LeBron the Wine Connoisseur, LeBron the Hip-Hop Ambassador is far more powerful, as he’s spent his NBA career running in the same circles as the rap game’s elite.

While transforming into one of the greatest basketball players of all time over the past two decades, King James has cemented his status as the NBA’s leading tastemaster for rap music. Making friends with the best rappers alive, appearing in music videos, gracing the covers of hip-hop magazines, and previewing unreleased tracks or co-signing new artists on his Instagram story, LeBron has displayed his potential as a future hip-hop mogul.

In light of the recent announcement that LeBron A&R’d 2 Chainz new album Rap or Go to the League, it’s time to look back at James’ history with rap, from 2003 until now. This is LeBron's road to becoming an A&R.