Tupac Shakur walked the walk and talked the talk, but by the time 1995 rolled around, the armor around the fiery rap leader began to fade.

In early 1994 he was found guilty of assaulting “Menace II Society” co-director Allen Hughes and served 15 days in jail. By the end of that year, he caught five bullets across his body during an infamous stickup by unknown assailants in the lobby of Quad Recording Studios. Days later, he was sentenced to eighteen months to four-and-a-half-years behind bars for sexual abuse stemming from a November 1993 incident in a New York luxury hotel. He would later serve 11 months on the charge. But even with all the odds weighed against him, ‘Pac, who battled with “the system” long before he was even born, still managed to prosper.

Like the age-old saying, pressure makes diamonds. So amid the shooting, trial, and media storm that pinned Shakur inside a prison cell at New York’s Clinton Correctional Facility in 1995, became the groundwork for his ultimate message in a bottle: Me Against the World.

Like Marvin Gaye did before him with What’s Going On? and Miles Davis with Kind of Blue, the product that followed Pac’s awakening revolutionized Black music. In its soulful instrumentation (“Dear Mama,” “Me Against the World”), genuine reflection (“So Many Tears,” “Lord Knows”), and eye-popping paranoia (“If I Die 2Nite,” “Death Around the Corner”), MATW tackled societal issues at the heart of ongoing call-for-action initiatives like Black Lives Matter, along with allowing room for ’Pac to swallow the chaos wrought by his hardcore persona, digest it into a soul-baring manifesto and belting out a masterpiece that became gospel for generations to come. And to think he accomplished this all over R&B production.

Today (March 14), 21 years later, Me Against the World remains as much a mouthpiece for our current societal and political complexion now, as it was for a generation emerging in March of 1995. In an attempt to retell the story and creation of Shakur’s magnum opus in its truest form, REVOLT embarked on a mission to speak to his collaborators (Easy Mo Bee, Money B) and friends (Leila Steinberg, E.D.I. Amin) to provide an intimate look at the icon and the masterstroke that became his spiritual autobiography.

The Squad:

Moe Z.M.D.: Producer of album cuts “Young Niggaz” and “Outlaw”

E.D.I. Amin: Member of Outlawz, appears on “Me Against the World” and “Outlawz”

Money B: Member of Digital Underground, collaborator

Ray Luv: Best friend, collaborator

Leila Steinberg: Former manager

Easy Mo Bee: Producer of album cuts “Temptations” and “If I Die 2Nite”

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1. This Thug’s Life

“This album was made before I went to jail, before I got shot, and all I’m talking about is going to jail and getting shot. So it was a prophecy. So when the album comes out and then you hear about what’s really going on in my real life, I mean, I don’t have to say I’m keeping it real, you could listen to the music and go, Whoa he said that…” — Interview at the Clinton Correctional Facility in New York (1995)

According to producer Moe Z.M.D., Tupac’s third studio album was originally going to be called Fuck the World. The title, of course, was reflective of the drama that surrounded the rapper at the time, from the arrests, the shootings, and several brushes with the law. Since 1993, the rapper was arrested six times in incidents ranging from assault to a gunfight with off-duty cops. However, after an indecent at the upscale Parker Meridien Hotel in New York City involving a 20-year-old woman on the night of Nov. 18, 1993, the legal drama came crashing down on the rapper. So during the making of 1994’s Thug Life, Vol. 1 , a compilation album with his Thug Life rap group, he began channeling this paranoia, anger, and pain into songs that would eventually get pieced together for his solo LP.

Moe Z.M.D.: Really his thought process when he talked to me about [the album] — it wasn’t called Me Against the World at first, I think it was called Fuck the World. He was just like feeling angry about all the stuff that was happening to him and he really just talked about dying and knowing that he was going to die and he needed to get all this truth out before it happened. He felt like people were coming for him and he was just uneasy about either the government, people from the street, you know, he was getting it from all kind of ways. So he wanted to really portray his anger at what was going on, so I think he kind of toned it down to Me Against the World because it was like the same theme without being so harsh.

E.D.I. Amin: What he was going through right at that point in his life. It was a turbulent time for him and he transferred it over to the music. It was very honest and very raw.

Money B: Once he went to jail, he had a lot of time to reflect and really speak from a point of vulnerability. So he was allowing himself to show a side of himself that you probably hadn’t seen from himself. 2Pacalypse Now and Strictly 4 My N.I.G.G.A.Z. he never really talked about his relationship with his mother and things like that.

Leila Steinberg: He was willing to be completely vulnerable and to invite you into his pain. When he wrote “Dear Mama,” [Ray Luv] was one of the first people he shared it with. He was really excited. I’ll never forget being in the apartment and just crying because we all have really powerful mothers who were in tremendous pain around their commitment to service and we suffered that. We suffered the generation of ’60s activists who were really hurt.

Ray Luv: The fact that it’s first single is “Dear Mama,” and the fact that the album is, maybe duplicitous is a dirty word, but it shows both sides of him as an individual [and] as an artist. I think most of when you hear somebody mimic Tupac, I think that they’re probably pulling from that record. I think that was the one that blasted him to superstardom for that reason. It’s raw, it was honest, and it came out during a cold time too, a lot of violence in the streets that was being reflected in the music, a lot of struggle.

E.D.I. Amin: One of the best songs on that album was obviously “Dear Mama.” It’s one of those songs that’s going to play forever. That’s when he went from being a really good hip-hop artist to being a voice.

Steinberg: ‘Pac was born to be political, he was born to touch the hearts of the world, and he did that. And that particular album, really took him into a political arena. It mobilized the hearts of the entire planet. There’s nobody that didn’t connect to at least one song on there, but it was an album that you could play from beginning to end. It was the narrative that introduced the world to him, because the first [albums] were really just him venting, this was his mobilizing.

Moe Z.M.D: The subjects that he touched on and the concepts and the stories, he wanted everyone to feel what the youth, as far as life, as far as the government, he touched on everything. He also had people guest spotting on there to give their story. Musically, all of the music was tailor made for the raps even though it was the other way around because he wrote to the tracks.

Easy Mo Bee: I always felt like that was one of the most different albums he did. At that time, up to that point, and even after when you look back, that album was just different. Always a brother to speak up and say his piece. He ain’t gonna hold whatever it is that he has to say, whether it be about some chick that he just dealt with last night or his feelings about the government or police brutality, what’s going on in the neighborhood, how us as Black people here in America get treated, he wasn’t afraid to speak about it all.

Ray Luv: I mean I think that’s why it had such a big impact [because] if you look at the two albums before it, they had some success. The second one was double platinum, double platinum single. But as far Tupac being the image that we have of him now, that took place during the creation of this record. He being shot, going to jail, and you don’t get a response from him, you don’t really hear what he has to say about how he feels, but the first thing you hear is “Dear Mama.” It was like a blues record, it wasn’t even like a rap record.

Steinberg: It was his Gil Scott-Heron record.

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2. Me (and the Team) Against The World

“No matter what these people say about me, my music does not glorify any image. My music is spiritual if you listen to it. It’s all about emotion. It’s all about life… I tell my inner most darkest secrets, I reveal myself in every one of my records. From “Dear Mama” to “So Many Tears,” I tell my own personal problems and people can relate to that I believe…”

On February 14, 1995, Tupac was sentenced to 1 1/2 to 4 1/2 years in prison on sexual assault charges related to the Parker Meridien Hotel incident. Now 23, the rapper, who was recovering from gunshot wounds suffered in a mugging inside Quad Recording Studios the week he was on trial, immediately began serving his time at Clinton Correctional Facility in distant Dannemora, New York. Due to the incarceration, the completion of Me Against the World would be handled by Outlawz member and friend E.D.I. Amin. Under his vision, the album was composed of records recorded during the Thug Life sessions. Featuring singles like “Dear Mama” and “Temptation,” the album debuted at No. 1 on the Billboard 200 chart and stayed atop for four straight weeks. The LP also surpassed Bruce Springsteen’s Greatest Hits in sales, which was previously the biggest selling album of that year.

E.D.I.: I kind of saw [the album] being made in the process piece by piece. Then towards the end of the project, he was unfortunately incarcerated and really didn’t have anybody he really trusted to handle and put the product together. So he asked me to fly out to L.A. and it was my first time [out here] alone and I got a chance to really just sit with the music, the engineers, producers, and really watch how it all came together. It was pretty much his vision and using me as an instrument to get it done.

Moe Z.M.D: When I first did the project, I was coming in on the tail end of the Thug Life, Vol. 1 album and they were just about to put out the first single, “Cradle to the Grave.” So they wanted me to remake it, because he had an issue with the producer I guess. So I remade it, I remade “Runnin’ From the Police,” and I remade “Lord Knows.” So then, he wanted to use “Cradle to the Grave” right away and then within days, flew me to New York to work on some more stuff because I had sent him a demo of some tracks. He was like, “I like most of tracks on there, but there’s this one on there that’s at the end,” and I’m like ‘Oh, that’s a R&B track that I had left by accident.’ So then he said, this is his words verbatim, “Well it’s a rap now nigga.” [Laughs] I said, Alright. That ended up being “Outlaw.”

Money B: That was one of favorites. One of my favorite songs on that album was “Outlaw.” I used to just bump that s * everyday when I first got the record. But my absolute favorite song on the album, and my absolute favorite Tupac song of all-time, is “So Many Tears.” That was the song for me. Produced by Shock G, you know Digital Underground. But that’s not the reason. For one, I always liked “That Girl,” which that harmonica is sampled in the song, that was always one of my favorite songs from Stevie Wonder when I was growing up. The way Shock uses the sample and just the lyrics, I totally felt that song. When I heard it, I was like, Okay that’s the Tupac I know.

Easy Mo Bee: I went to Rucker Park because at the time he was filming “Above the Rim.” So I go in the trailer, I had AB Money and J.R with me, I played him one joint that I had already made and that track ended up being “Temptations.” I had took “Computer Love” and flipped it. All the beatmakers out there, a lot of people know but a lot of people don’t, it was [Zapp & Roger’s] “Computer Love” filtered and I’m drumming it up on top then I’m letting some keys and stuff. Then after the beat is done, I had this idea, I was listening to Redman’s album (What Thee Album) heavy and on that joint there’s a track with Erick Sermon (“Watch Yo Nuggets”) where it goes “Heeeey Erick Sermon… Haaaaay.” So I’m like, just take the Hey and Hay and try it out. And that’s how we got that beat right there.

Moe Z.M.D: For “Young Niggaz” we were in the studio working on a song called “Throw Ya Hands Up” and [Pac] gave me a cassette of Cameo and said, “Do “She Strange,” just flip it.” So I said okay and went back to the crib and at that time my equipment was broken down so I called up my homeboy, who I call my cousin, named Lethal, and [asked] if I could program the record on his equipment and take it to the studio and cut it. He was like, ‘Yeah no problem.’ So I cut it up and everything, did it, went back to the crib, came back in the morning so we could go to the studio and he was like, “I added a little part to it.”

So it was this little breakdown, you know where Pac talks in the middle of the song, and I was like, ‘You know what talk to the label, get your co-production [credit] and everything. So went to the studio, cut the track, Pac came in [and] started writing to it and I tried to get my homeboy that sings on “Cradle to the Grave” on it, but he was doing something at the time so I got my dude G-Money, who actually sang with my other dude Radio, which is how ‘Pac found me because they were on Interscope too, and so it went from there and he loved it. That’s one of the [songs] I got a couple of my artists singing too in the background, including me.

Easy Mo Bee: During our session, I’m thinking that all this stuff we recording is going on the Me Against the World album. No, this dude [just] recorded a big batch of songs. He did one of the smartest things in the world, he took “Temptations” and “If I Die 2nite” and put it on Me Against the World. He takes “Str8 Ballin’” and puts that on Thug Life, Vol. 1. Then he takes “My Block” and puts it on “The Show” soundtrack.

E.D.I.: Definitely him and Easy Mo Bee had incredible chemistry. A lot of those songs that they did together, even a couple that didn’t make the album, are all classics. It was [also] one of the first times you heard the chemistry between him with Johnny J, who did “Death Around the Corner.” It was a lot of good producers on there, of course Mike Mosley, but for the most part every producer on that album catered to his sound and really came up with a cohesive sound for his project.

Moe Z.M.D: I was in on a few of those recording sessions that he had with a couple other people and it was the same thing, looking at it like, This is amazing. There was never a dull moment. Half the time, us as producers, we didn’t really know what was going on, we knew we wanted to make good music, but we didn’t know that it was going to be what it is we wanted it to be. The ones he had on there, they really cared about the sound and they cared about how to make his words come across and it even went down to the mixing, the people that he chose to mix certain things. It was like they really wanted you to hear and feel what he was saying versus just throwing him a track to rap on it.

E.D.I.: It’s a really good album from start to finish the production is high quality. I think that’s when Pac took the music he was rapping over a little bit more seriously. Up until that point, he was more focused on the message and he didn’t really care that much about the beat. I think Me Against the World he started to really pay attention to the beats he chose, so it’s really good production, the features on there are all solid and it’s just a cohesive project.

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3. Thuggin’ Eternal

“I think I did real deep with this album. As far as the success… I owe it all to my fans, I owe it all to the people who supported me. I think the reason being is that every album, if you go backwards and listen to the other albums I’ve put out, it was a prophecy…”

When it comes to Me Against the World , the critics and fans recognize this as a masterpiece within Tupac’s revered catalog. However, among albums like 2Pacalypse Now and All Eyez On Me , it’s its most approachable and earnest album yet. It showcased the rapper’s human side by portraying him at his most vulnerable (“When I die, baptize in eternal fire, I’ll shed so many tears”) and politically-charged. These messages provide the kind of societal detritus that would lay the foundation and voice for galvanizing Black identity in works like Kendrick Lamar’s To Pimp A Butterfly . It’s not only a classic album, but a definitive memo to the youth of America.

Ray Luv: That [album], it was just that point for him where he had nothing else left to hide. And that is liberating place to be at as an artist. But as a listener, it’s like, you can’t stop listening. I just kept listening to that record, over and over again, and we were all recording at that time. We were all releasing projects and it was just one of those ones where you didn’t just listen to it because you knew him and he was your friend, it became a part of my life.

Steinberg: You either loved ‘Pac, or you hated him. He was the voice of one’s violence is equivalent to one’s pain. He was angry and he was hurting. It wasn’t me against humanity or the people, it was me against a system that has oppressed women and all people of color, but in this country primarily Black people and he was always so burdened by the pain of making a difference [that] he couldn’t even enjoy his life.

This record was the transition because he was hungry up until the release of Me Against the World. He was still financially struggling and so he actually was able to have more fun and laugh a little on the way to that point. But, all of a sudden the world started interrupting and cases started happening and that’s what we’ve systematically done to oppress people of color, especially with the power that ‘Pac had, ‘Pac had the power to unite the planet.

Ray Luv: We really did believe like we were going to change the world. Steve Jobs had a great quote that went, “The people that are crazier to think that they can change the world usually are the ones that do.” And all of us, the movies, the books, the international impact, he believed in all of them since day one.

Steinberg: He was committed to social and political justice and it’s a costly commitment and Me Against the World was his statement and he was standing up. It didn’t matter who what or when, we knew we wouldn’t have ‘Pac forever. Hindsight doesn’t mean anything or I would definitely have created something different and been a better guide. I would’ve really insisted that he stopped speaking that he couldn’t be here and that he couldn’t live and still have the impact.

Ray Luv: I think [he] understood too that there’s a time for martyrs. Sometimes it gets people’s attention. I think Tupac’s death was such a huge shock, not so much to us in the Black community, which it was a shock, but I think like to white kids in Iowa and people in college, it was like “What, he’s dead?” I think him laying the groundwork for what was his great work to bring focus to the fact that it’s happening to all of us. It could be me, it could be B.I.G., it could be anybody and it’s not just the little skirmishes between us, it’s the climate outside, it’s the way things are.

Sternberg: It’s almost surreal that we sit here talking about him, but he always told us we would. He was really clear early on when we all worked together that he wouldn’t be here, he would never be here to really appreciate and kind of participate in his impact. He didn’t get to grow up. So, here we are responsible for continuing.