Hip-hop and sports have gone hand in hand dating back to the culture's earliest days. Whether it be basketball, boxing or anything in between, rappers have always felt a kinship with world class athletes, comparing their prowess in their respective sport with their lyrical skill when behind a mic.

From Kurtis Blow crafting a song celebrating the blacktop version of the round ball on "Basketball" to Jay Z practicing breath control to build up his stamina as a an MC on "Lyrical Exercise," or proclaiming himself the Michael Jordan of rap, the notion that rappers truly have a burning desire to have the discipline and attributes of a professional athlete has been proven time and time again.

And this concept doesn't only extend to beats and rhymes, but in terms of business and alliances as well. In many professional sports leagues, when a player's contract with an organization runs its course, they have the option of either resigning with said team or club, or to explore their options via free agency. Examples of this that have made headlines over the past few years is LeBron James' decision not to resign with the Miami Heat and come back to the Cleveland Cavaliers, as well as Kevin Durant opting to break free of his ties to Russell Westbrook and the Oklahoma City Thunder and completing the NBA's latest super team, the Golden State Warriors.

However, there are also a few instances in which players flirt with free agency, but ultimately choose to re-up with their organization, including Carmelo Anthony and Demar Derozan. The rap game is no different and has seen a multitude of artists be tasked with making similar decisions to their counterparts in the NBA, NFL and beyond. After taking a trip down memory lane, we remember 20 free agents in rap, from Nas to 2Pac to Lil Wayne and more, that made major waves over the past two decades.

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