He calls himself the new Sinatra, rap’s Grateful Dead, and the Mike Jordan of recordin’. Jay-Z knows that in hip-hop, he’s in a category of his own–he has to go outside his own profession to find any comparison to his success, longevity, and technical proficiency. He outlived his closest peer, The Notorious B.I.G., and then proceeded to outwit and outlast every other rapper who went platinum in the 1990s.

Shawn Corey Carter’s greatness wasn’t always a foregone conclusion, though. His first recorded appearance, a split second cameo on mentor Jaz’s 1989 novelty “Hawaiian Sophie,” wasn’t exactly an auspicious debut on the level of Nas’ “Live at the Barbecue” verse. Jay didn’t release his first album until he was 26, an age by which many rappers are already washed up. “Reasonable Doubt was a classic, should’ve went triple,” but it didn’t–instead, it was his third album, 1998’s Vol. 2…Hard Knock Life, that moved millions of units and put Jiggaman on a perch that he has scarcely budged from in the two decades since.

From the career-defining The Blueprint to the premature farewell of The Black Album, from the epic Kanye West collab project Watch The Throne to his first Album of the Year nod from the Grammys for 2017’s boldly personal 4:44, Jay-Z has become hip-hop’s premier album artist. On every new LP or densely allusive guest verse, you get a peek behind the curtain at a life that took him from the Marcy Projects and a risky stint as a street hustler to a life of arena tours, huge business ventures, and a marriage with Beyoncé. He’s got more bangers than just about anybody, but we took the time to narrow down the 100 best Jay-Z songs.