It is a strange misfortune. Despite their many successes, legends like JAY-Z, Snoop Dogg, and Nas are now cursed with the unhappy fate of growing older, less interested, and ever more mortal. Death, on the other hand, preserves. The Notorious B.I.G., Big L, and Aaliyah will always be in their prime.

Nobody benefits from this gone-too-soon bonus more than Tupac Shakur.

By 1996, 2Pac was at the center of a violent explosion of creativity and media-saturated drama. Then he was struck down in mythical fashion—something he called for early and often, in both word and deed—in Las Vegas, on September 17 of that year. His killer remains at large, though numerous conspiracies unsurprisingly point to Suge Knight.  

In the years following his death, Pac was ready-made for Internet godhood: His life was fully documented and rife with street intrigue, conspiracy theories, and a massive collection of songs, video, the works—a fully scripted multimedia docudrama.

Twenty years later, Tupac's image as king rebel poet and unrelenting voice against injustice remains untouched by the ravages of time and commerce. Imagine if JAY had lived through the release of The Blueprint and then got cut down right before dropping The Black Album. How many churches would have been erected in his honor of him and music? Instead, he has to contend with rumors about the Illuminati and faking a pregnancy.




Pac struck mythic chords in large part because he was all in. His records are a testimony to his complete commitment to building his own legend. He tapped into the matrix like Neo, finding a formula that resonates around the globe. A formula only a handful of artists ever attain. Like his Peruvian namesake (we dare you to Google Tupac Amaru—ill), Pac consciously made himself a sacrifice. It also made him one of the most prescient and influential artist of his time. Just like he planned it.

Makaveli remains one of the greatest because he is still here. Not in some Cuban hideaway, but in hip-hop’s every nook and cranny. We see his tattoo game reflected in how overboard the ink thing has gotten. T.H.U.G. L.I.F.E. begat Fear God begat thunderous ice cream Brr-Brrs. We see his hyper-prolific approach to recording becoming the standard on the mixtape circuit, partly thanks to his great fan and acolyte Lil Wayne. And we've seen his rebellion become a commodity that can be mass-produced.

Wayne, JAY, 50, and T.I. all borrowed and reconfigured the blueprint Pac authored. We can go on and on. But there's one thing about Pac nobody has been able to duplicate: He bared his soul, to its very core.

Intense and passionate, Pac ran with thugs and killers, starred in a cult classic, and shot cops and walked free—only to be shot five times, survive and then go to prison and be reborn. But somehow he remains the rapper that your mama could love. Very few have been able to manage this sort of high-wire act with such bluster. He didn't live long enough to become a rap mogul, but his outsized presence in America's pop culture landscape cannot be overstated.

Pac lacked the intricate rhymes or flow patterns deemed worthy of praise by rap puritans, but his sometimes prophetic lyricism ran the gamut from player to rider to revolutionary. As such, he remains the blueprint for 75% of these so-called rappers out here. Here is a walk through the many highlights of one of hip-hop’s most influential artists—one that set the tone for all that would come after it. These are the best Tupac songs.