Twenty years ago (September 13, 1996) Tupac Amaru Shakur died in the University Medical Center of Southern Nevada. The last year of his life had been his most successful, his most active, and certainly bid to be his most controversial. Shakur, who was born in New York, became a young man in Baltimore, and immortalized in California, left the world at the top of his game. He delivered the concept of “Thug Life” to living rooms and classrooms, prisons and poetry forums—up for the world’s interpretation. The actual rapping abilities of Tupac (or “2Pac” as his albums were stylized) are widely debated, especially for an MC who appeared to detest revision and maintained often unconventional taste in beats. However, two decades after he was taken from us by the same street violence he often illustrated in his music, ‘Pac is definitively the most influential rapper Hip-Hop has ever known.

One of the most interesting qualities about Tupac Shakur is that he released all of his albums, while alive, within a five-year span. For perspective, the time between Shakur’s late ’91 debut 2Pacalypse Now and his death is roughly the same amount of time that has passed since Kendrick Lamar released breakthrough Section.80 to now.

Like many others, Tupac’s introduction came by way of a high profile guest appearance. Digital Underground’s “Same Song” made a big to do, with its Nothing But Trouble promotional music video about the featured MC (who was a dancer-roadie with the Oakland, California group). Still, the moment does not stand up to iconic ’90s MC introductions such as “Live At The Barbeque” for Nas or “Deep Cover” for Snoop Dogg.

While his early material is rarely his most discussed, it is consistent with the music he made at the top of his game. Songs like “Static” (an early demo track later released on many bootlegs and compilations) show the agenda that ‘Pac honored ’til his tragic end.

“Static is the last thing you need when you see me
Better have a bat or a gat to defeat me
Nigga, I’m a whole possé rolled into one shot
Takin’ all you got”

Whether true or not, Tupac, like several of his film characters, portrayed blind courage. He was a 5’9″ soldier who stared any and all obstacles in the eyes. ‘Pac entered the scene fighting big ideas—crooked cops, unplanned teen pregnancy, and institutionalized racism. Later, that same vitriol was aimed at artists and record labels. Nevertheless, Tupac knew he may never be the best, so he positioned himself as the most charismatic, the loudest, and absolutely the feistiest. Looking at the most meaningful groups at the time of his entry to the industry, ‘Pac appeared to be the yin and yang in each–he was both Flava and Chuck, Cube and Eazy, and Bill and ‘Face. He used spectacle to draw more attention to the his substance. For every “Hit ‘Em Up,” there is an “Only God Can Judge Me” or a “Life Goes On.” This formula worked—for an artist who could be conscious and gangsta, profane and profound.

Moreover, Shakur knew how to talk to anybody, seemingly at any time. He showed his humanity to MTV’s Tabitha Soren at a time when he was regularly presented in pop culture as a menace. By contrast, he defended his thug persona while speaking to BET’s Ed Gordon, explaining it as a means to relate to everyday people.

A Handwritten Letter from Tupac Confirms He Had Plans to Unify the Coasts.

Among his many facets, Shakur could ham it up, too. A musical theater performer in his youth, the MC joined Ice-T on FOX shortly before his death to do a singing duet cover of Barbara Streisand’s “You Don’t Bring Me Flowers.” Two of the coldest Rap personas showed sensitivity, vulnerability and softness. This is Drake on “SNL,” 20 years ahead of its time. ‘Pac could poke fun at himself even when he also demanded to be taken more seriously than seemingly any artist of his stature to date. Even then, if what he reportedly said (something to the effect of “I’m just trying to get this money”) to Biggie at the red carpet of the 1996 MTV Video Music Awards is true, he knew he was playing to the crowd above all else.

Read Tupac’s 1995 Letter From Prison To Public Enemy’s Chuck D

In many facets, Shakur’s later albums set the trend for the collaborative landscape in Hip-Hop today. Tupac turned his releases into a system of alliances, callbacks, and key promotional spots. On All Eyez On Me, he involved Redman and Method Man, two pillars of the East Coast movement—when  ‘Pac was accused of hating a whole coast. He saw the talent in seemed-to-be marginal artists like Bad Azz, Swoop G, and Heavy D’s DJ, Eddie F—making songs just as ripe and rich as his works with Snoop, Scarface, or Shock G. Today, we see the continuation of that strategic thinking when Kendrick Lamar seeks out MC Eiht for his moment, Wiz hoists up a Juicy J as part of his movement, and Game structures his album personnel as conversation pieces.

A key collaborator, Dr. Dre, gave Tupac his first (and arguably his only) #1 single. Within months of late 1995’s “California Love” two-pronged smash, ‘Pac had turned on Dre—questioning his sexuality, his loyalty, and reportedly partaking in at least one beat-down of Dre’s understudy, Sam Sneed. Three years after his death, Dre commented, asking the world, “How much Tupac in you, you got?” Hip-Hop has tried to answer that question for two decades.

The reality is, Shakur was (and remains) a tapestry of contradiction—the only rapper with the courage to risk his first solo single to describe a dumpster baby, and the audacity to try to justify sexism five short years later on “Wonda Why They Call U Bitch.” He showed us the best and the worst in ourselves, and died in a blaze of glory so that Rap would forever have a guard rail for when keeping it real started going tragically wrong.

Producer Mike Mosley Reveals Several MCs Who Witnessed Tupac Record “Hit ‘Em Up” (Video)

“Ambitionz Az A Ridah,” one of Pac’s most popular songs to date, proved to be one of his most prophetic, as well. Some of its lyrics read:

So many battlefield scars while driven in plush cars
This life as a rap star is nothin without heart
Was born rough and rugged, addressin the mad public
My attitude was, Fuck it, cause motherfuckers love it
To be a soldier, must maintain composure at ease
Though life is complicated, only what you make it to be

Exactly seven months to the day after that song hit the ears of the public, Shakur died. He was killed while riding in a plush car—believed to have been the consequence of showing his heart in the MGM Casino lobby. Life is truly what you make it to be. Shakur made his fast, intense, bold, dramatized, and full of ambition.

Jake Paine is the Editor-in-Chief of Ambrosia For Heads. Since 2001, he has covered Hip-Hop and entertainment for online, print, radio, and in video.