Brooklyn’s Shawn “JAY-Z” Carter had already been a well-charting rapper for a few years when he leveled up with his 1998 breakthrough, the Annie-sampling “Hard Knock Life (Ghetto Anthem).” But that sizable hit allowed the former drug dealer to fully graduate “from grams to Grammys”—as he later rapped—and make a convincing case for being the world’s greatest MC. While early hits like 2000’s “Big Pimpin’” leaned hard into that street cred, by the following year he had perfected his self-mythologized image as an unbeatable rapper turned cigar-puffing mogul with “Izzo (H.O.V.A.)” and its culture-shifting source album The Blueprint. Carter’s dream combination of lyrical dexterity, commercial polish, unshakable swagger, and artistic risk-taking came through in repeat collabs with rising producers like Kanye West and Just Blaze, not to mention such industry mainstays as Timbaland on “Dirt off Your Shoulder” and Rick Rubin on “99 Problems,” both from 2004. With 2009’s Alicia Keys teamup “Empire State of Mind,” Carter proved that he could command a pop smash while retaining his hip-hop bona fides and shrugging off multiple would-be retirements. He continued to work with West even after the latter had become a rapper and household name in his own right, leading to multiple hits like 2011’s “Ni**as in Paris” and “Otis.” Even once Carter slowed down in the years since 2013’s Justin Timberlake collab “Holy Grail,” he has remained a very visible public supporter of his wife Beyoncé and a permanent fixture on rap’s Mount Rushmore.