Twenty years ago today, Tupac Shakur’s third solo album, Me Against the World, hit stores in a time before streaming services, during an era when compact discs were still the music delivery medium of choice. Over 7,000 suns have set since that winter day and much has happened in the interim: Y2K, 9/11 and the “War on Terror” that followed, Hurricane Katrina, and the election of Barack Obama, the United States’ first black President. Many new pages in Hip Hop’s history have been written as well: The collapse of Death Row Records, the rise of the “Shiny Suit Era,” Jay Z versus Nas, Eminem, Kanye West, and, most pertinent to this reminiscence, the murder of Tupac himself. Listening to Me Against the World two decades after its release, it is hard to believe that rap music’s greatest icon has been gone for so long. Tupac’s passionate delivery has lost none of its immediacy, his rhymes none of their relevancy. Me Against the World is where Tupac became more than a rap star, taking his place alongside Kurt Cobain as their generation’s greatest spokesmen. Two decades on, this album remains one of the most beloved, important, and appropriately titled in Hip Hop’s catalogue of great works.

Tupac Shakur’s Legal Troubles

“It’s called Me Against the World. So that is my truth,” he stated in a rare 1995 prison interview. It truly felt like it was Tupac against the world when he cut this record in various California and New York recording studios in 1993 and 1994. Those years were two of the most turbulent in a tragically brief life that was already scarred by poverty, drug abuse, police harassment, imprisonment, and death. In 1993 alone Tupac was charged with assaulting a limousine driver, arrested for shooting two off-duty Atlanta police officers who were harassing an African-American motorist, and prosecuted for sexually assaulting a 19-year old woman in New York. The following year was no easier for him. While the sexual assault case made its way through discovery, Tupac served 15 days in a Los Angeles jail for assaulting Allen Hughes (of the Hughes Brothers, the directors of Menace II 2 Society, among other films) and his song “Soulja’s Story” was accused of inciting the murder of a police officer in Milwaukee. Most infamously, on the eve of the sexual assault jury’s verdict, Tupac was pistol whipped, stomped, and shot five times for resisting an armed robbery in the elevator of Quad Studios in New York. (Contrary to some books and articles published in this album’s aftermath, Me Against the World was not recorded after Tupac was ambushed on November 30, 1994; the only reference to that botched robbery comes in the album’s Tupac-less “Intro”). The day after he was shot, a wheelchair bound Tupac was found guilty of sex-abuse, i.e., forcefully touching his accuser’s buttocks, despite his protestations of innocence and his prior sexual history with his accuser. Fortunately for his career (and his attorneys’ coffers), Tupac’s relentless work ethic was undisturbed by the chaos rife during the years prior to his conviction. In 1993 and 1994, he starred in two major motion pictures (Poetic Justice and Above the Rim), released two albums (Strictly 4 My N.I.G.G.A.Z… and Thug Life’s Volume 1), and recorded Me Against the World, one of the genre’s bona fide masterpieces.

On March 14, 1995, Tupac, who was just 23 years old at the time, was confined to a cell at the Clinton Correctional Facility, a maximum security penitentiary in Dannemora, New York. His music career seemed in jeopardy. Though some hoped that the isolation might fuel his creativity, Tupac was rarely inspired to write songs in prison. He told Kevin Powell, a journalist and author who is currently writing a Tupac biography, that in prison “I don’t even got the thrill to rap no more… In here I don’t even remember my lyrics.” In fact, until Tupac was provoked by disparaging comments made by Bad Boy Records CEO Sean Combs (Puff Daddy) in an August 1995 Vibe magazine interview, he seriously considered making Me Against the World his last album. “This is my best album yet,” he said. “And because I already laid it down, I can be free.”

Thankfully, Tupac did not hang up his microphone, although his incarceration did make it extremely difficult for him to promote Me Against the World. He could not appear in any of the music videos that followed its release and rarely gave interviews. In spite of this handicap, the album quickly became the most commercially successful of his career to that point. It debuted at #1 on Billboard’s 200 pop album chart (a first for Tupac) and made him the first prison inmate with a number one album (Lil’ Wayne repeated the feat in 2010). “Every time [corrections officers] used to say something bad to me,” he said, “I’d be like, ‘That’s alright, I got the number one record in the country right now… I just beat Bruce Springsteen.’ And they used to be like, ‘Go back to your cell.’”

Me Against the World had staying power on the charts as well. It stayed atop the Top 200 for four straight weeks and spawned three singles that stormed Billboard’s Hot 100 singles chart (“Dear Mama,” Tupac’s heartfelt ode to his mother, Afeni Shakur, was the most popular of the three). On December 6, 1995, Me Against the World was certified double platinum (two million units sold) and, as of September 2011, has sold over three and a half million copies.

Me Against The World’s Critical Reception

As with most of Tupac’s works, Me Against the World was received more positively by Hip Hop fans than by contemporary critics. Though many critics applauded the album’s introspection and thematic consistency (apparently immune to the appeal of Tupac’s Gemini duality), some mistook Tupac’s sincerity for pure performance, patronizing his earnest desire to relate the struggles he was going through. “Everybody thought I was living so well and doing so good that I wanted to explain it. And it took a whole album to get it out,” Tupac explained. Cheo Hodari Coker’s review in Rolling Stone exemplifies the cynical lens music journalists have often used to evaluate Tupac’s artistry. In that review, Coker labels Tupac as a “character” on more than one occasion, focuses on Tupac’s “contradictions,” and tempers his praise by describing the title track as “formulaic, radio-friendly material.” Like Coker’s (who gave Me Against the World just three and a half stars out of five), The Source’s rating seems low in hindsight. That magazine, then the bible for Hip Hop’s cognoscenti, originally awarded the album only four “mics” out of five despite concluding that “[a]ny complaints critics and fans alike had about Tupac’s last two albums can be put to rest.” Rap music critics weren’t the only New York-based journalists questioning Tupac’s “character” around the time of this album’s release. Most painfully, Touré, currently an MSNBC talking head, described Tupac as “a master performance artist whose canvas is his body and whose stage is the world” in an editorial for the Village Voice that was published in the aftermath of the Quad Studios assault. Tupac read that editorial in his hospital bed and cried, furious at the implication that the robbery was staged to promote his Thug Life “image” (rap artist Rick Ross was subjected to similar speculation when his Rolls-Royce was fired upon in 2013).

Despite the slights, many critics, including Coker, had to admit the growth Tupac exhibited on Me Against the World. The New York Times, of all sources, astutely observed the message behind the music, anointing Tupac the “St. Augustine of gangster rap: after leading a life of sin, he wants to steer others away from his own mistakes.” Me Against the World was also remembered when award season came around. It won Rap Album of the Year at the 1996 Soul Train Music Awards and was nominated for Best Rap Album at the 1996 Grammy Awards (losing to Naughty by Nature’s Poverty’s Paradise). Tupac aimed for such praise when recording the album. “Me Against the World was really to show people that this is an art to me, that I do take it like that.” Pac said in the book, Tupac: The Resurrection 1971-1996. “And whatever mistakes I make, I make out of ignorance, not out of disrespect to music or the art.”

The Me Against The World Legacy

Like fine wine, the passage of time has been kind to Tupac’s third LP. In March 2002, The Source increased Me Against the World’s rating to five mics, the highest honor that magazine can bestow on an album. Other critics, like AllMusic’s Steve Huey, hailed it as “the best place to go to understand why 2pac is so revered” following Tupac’s death in 1996. Perhaps most flattering of all, Me Against the World’s lead single, “Dear Mama,” became just the third Hip Hop song ever entered into the Library of Congress for cultural preservation in 2010.

Why has Me Against the World persisted while other multi-platinum contemporary albums like Coolio’s Gangsta’s Paradise have faded in Hip Hop’s collective consciousness? A large part of its staying power is undoubtedly Tupac’s fascinating life and untimely death, which he frequently prophesized on tracks like “So Many Tears” and “Death Around the Corner.” Tupac’s confessional lyrics draw listeners in, revealing his fears, despair, wisdom, and melancholic nostalgia. The fearless honesty of songs like “Lord Knows,” where he laments, “I’m hopeless / They should have killed me as a baby / Now they got me trapped in the storm, I’m goin’ crazy,” makes this one of Hip Hop’s most personal albums. Kendrick Lamar, the West Coast’s latest savior, agrees. In 2012, he listed Me Against the World as one of his 25 favorite albums and told Complex that “you can tell what type of space [Tupac] was in” when he recorded it.

The most important reason why this album endures is simple: it is a damn good record. Its singles, “Dear Mama” (one of the most influential rap songs ever recorded) and “So Many Tears” (the preferred Tupac song of the Digital Underground’s Money-B) in particular, are some of Tupac’s best. The rest of Me Against the World is no slouch either. Deep album cuts like the title track (the third verse of which is one of Tupac’s most celebrated), “Old School” (Tupac’s tribute to the Hip Hop of his youth), “If I Die 2Nite” (one of Tupac’s most poetic lyrical performances), and others all help round out its 66-minute running time. It rewards repeat listeners and rarely sags under the weight of the dirge-like atmosphere Tupac created.

The Tupac who gave birth to Me Against the World is the Tupac many listeners most want to remember: a young man with an old soul, beaten down by society and desperate to express his vision of the world around him, unburdened by the beefs that plagued the last year of his life. It is kind of ironic that many of those who most love Tupac and his music would become so attached to this aural snapshot of his life, when he was at his lowest and the whole world seemed allied against him. Maybe that is an appropriate legacy for Hip Hop’s most divided (and divisive) artist.

Michael Namikas is a writer and longtime Hip Hop listener who practiced law in a past life and is currently writing a listener’s guide devoted to the music of Tupac Shakur, the first volume of which will be published in the first quarter of 2016. He frequently posts on Reddit as /u/Mikeaveli2682 and can be followed on Twitter @Mikeaveli2682.