Since President Donald Trump's rise as a businessman and political figure, he has been a subject of fascination in hip-hop culture.

Rap music, with its braggadocious fixation on financial success, has named-dropped the billionaire CEO on dozens of occasions. He has been highly revered as a symbol of success, going as far back as Wu-Tang Clan's Raekwon in his 1995 record "Incarcerated Scarfaces," in which he calls himself the "Black Trump."

But after the 2016 election, the messaging about Trump − from gangsta rap artists like YG to lyricists like Kendrick Lamar − has largely turned from heralding to scorn. That's not to say all of hip-hop has turned its back on the president, especially when a pardon for disgraced music mogul Sean "Diddy" Combs is on the table.

Trump has publicly discussed the possibility of issuing a presidential pardon to Combs, who was found guilty in July on two counts of transportation to engage in prostitution following a landmark sex-trafficking trial in Manhattan court. Despite repeated attempts at bail, the Grammy-winning rapper has been incarcerated at Brooklyn's Metropolitan Detention Center since his arrest on Sept. 16, 2024.

During an Aug. 1 interview on Newsmax, the president spoke about potential pardons for Combs, convicted sex trafficker Ghislaine Maxwell and former Rep. George Santos. When asked directly about pardoning Combs by host Rob Finnerty, Trump kept mum on confirming his release but said that negative comments that Combs previously made about him would make it "more difficult."