Outspoken, misunderstood, and yet an icon to many, Tupac Shakur became the face of rap in the 1990s before his murder in 1996. His life and music were filled with controversy, but they were also filled with insight, intelligence, and heart.
420 to 30: A Music Retrospective
Here's 7 of my favorites from 2Pac (also known as Makaveli).
Week 7: 2PAC


#043/420 - Makaveli feat. Val Young, “To Live & Die in L.A.”

For 2Pac’s final album, he would switch it up and release it as “Makaveli”, naming himself after 16th century Italian philosopher Niccolò Machiavelli, namely after reading The Prince. While I haven’t had the prison sentence to really knock out Machiavelli’s works yet like Pac, as someone who also named themselves after something they got from an old book dealing with oppression, I feel like I at least get it to a degree. (And to make things meta, 2Pac samples Prince on this track.)
This song has things going from “California Love” where 2Pac and Dr. Dre are Mad Max BFFs, to "California Love part mothafuckin' two, without gay ass Dre”.
I mean, c’mon, who would ever have wanted to shoot this guy?
2Pac was very outspoken, but those are the best of us I think. How dull would our sense of taste be without spice and how morose our vision without red? Whether he was always “right” or not is subjective in each instance, but whatever he had to say was always worth being said.
Sometimes, maybe a bit juvenile, but keep in mind at his oldest he was 25.
Also, gotta love 2Pac Jesus on the cover.

#044/420 - 2Pac feat. Eric Williams, “Do For Love”

One glaring element of 2Pac’s catalog that makes it unique is that 6 of his 10 “studio albums” were released after he died, and 5 of those (and why I use quotations) were made without his final input, the last being released a full decade after his death. How could he have possibly recorded this much unreleased material? Well, while he did leave behind an immense amount of recordings (enough to be the narrator of his own posthumous documentary) after the first two or so, you start getting some repurposed verses, and you even start getting some retimed to fit a chorus better. So, in actuality, they were milking it for every last penny at a certain point, and it was as if every emcee needed a chance to make “their” 2Pac song. But early on, there were still some worthwhile instances of quality unreleased material, and this song is a good example.
Featuring Blackstreet’s Eric Williams singing Bobby Caldwell, this song is emblematic of the posthumous releases by 2Pac overseen by his mother Afeni Shakur in that it features a much catchier and prominent and poppy chorus than what 2Pac typically put out himself. It is definitely a change in his style, but I think the pair has an interesting effect. While the songs that 2Pac released himself were harder and better at being gangsta rap, maybe having his mother putting the her touch on songs like this one illuminated the more feminine/gentle/vulnerable side of Tupac Shakur.
Either way, it’s a nice fusion of genres, taking that late 90s R&B sound made much more enjoyable through Tupac. And also this song takes me back to hot nights in Phoenix delivering pizzas, listening to 90s hip hop in the old Saturn, counting down to the joint under the quilt in my trunk at the end of my shift. And that’s just a nostalgic time.

#045/420 - Makaveli feat. The Outlawz and Prince Ital Joe, “Hail Mary”

One of 2Pac’s most highly regarded songs, which was apparently created within the span of a single hour, writing and all.
“Picture paragraphs unloaded, wise words being quoted,” it’s pretty impressive and rightly mentioned along with his best works. I mean, I was never really sure who those other guys were on the song, but hey, I mean, I was never quite sure what the 7 day theory was either. Props to 2Pac for throwing out all this cryptic shit right before he died.

#046/420 - 2Pac feat. Talent, “Changes”

So, some will say, “if at first you don’t succeed — try, try again,” and apparently that was their motto in trying to Frankenstein these verses from 2Pac into a new song after he died. "I Wonder If Heaven Got a Ghetto” started as B-side, was remixed twice for his first posthumous album, and then (in part) became this song. Interestingly enough though, this version has become perhaps his most well-known song.
Some of his most famous lyrics come from this one, “Take the evil out the people, they'll be acting right ‘cause both black and white are smoking crack tonight and the only time we chill is when we kill each other. It takes skill to be real, time to heal each other. And although it seems heaven-sent, we ain't ready to see a black president. It ain't a secret, don't conceal the fact, the penitentiary's packed, and it's filled with blacks.” It’s hard to believe these words were being recorded the year my little sister was born, who is turning 26 this month, and yet seem as though they could have been written today. Really, it almost seems as though they should have been written today, they are even more appropriate and insightful now.
On one hand, there is enough great music in 2Pac’s first 5 albums to completely ignore the sometimes embarrassing remixes to come after his death, but I think the whole angelic Bruce Hornsby choir angle they took on this underlines what he was saying in a really striking, memorable way. I mean, most of this recording was just sitting there for 5 years or so otherwise, so it’s actually pretty cool that it eventually turned into this.
Also, listen to the quality of 2Pac’s voice on this song. He also had an acting career which clearly seems to have benefitted him as a rapper as he was able to express/act in the exact appropriate manner to give you the clearest idea of what he was not only saying but emoting with every line he performed. Add that he wasn’t too raspy, wasn’t too whiny, wasn’t too hard, wasn’t too soft, wasn’t too chill, wasn’t too crazy, and yet wasn’t too vanilla either. It ain’t hard 2 find why we lost a good one in 1996.

#047/420 - 2Pac feat. Snoop Dogg, “2 of Amerikaz Most Wanted”

“Ain’t nothing but a gangsta party” on this track. 2Pac and Snoop Dogg together, what more could you ask for from a mid 90s rap collaboration? What? You would also like to add Notorious B.I.G. and Eazy-E you say? Okay, well, yes that would be even better I suppose but Eazy-E did die in 1995 and this was released in 1996 so I’m not sure—okay. You know what? We got 2Pac and Snoop Dogg, alright? You can’t be complaining! That’s bastante!
So many great utterances in the song, “two multi-millionaire motherfuckers catchin’ cases”, “everybody in the party doin' dope-slangin’”, and of course who could forget “it ain’t nothing but motherfucking gangsta party”.
It’s probably the most fun you hear 2Pac having on any of his songs, which makes sense because these two must have gotten ripped as fuck together.
I don’t know how I feel about the whole hologram thing, but it’s a great song and my favorite collaboration of 2Pac’s.

#048/420 - 2Pac, “Life Goes On”

A song that only grew in meaning after 2Pac was shot and killed in 1996. It features my favorite verse from any 2Pac song.
“Bury me smiling with G's in my pocket. Have a party at my funeral, let every rapper rock it. Let the hoes that I used to know from way before kiss me from my head to my toe. Give me a paper and a pen so I can write about my life of sin, a couple bottles of gin in case I don't get in. Tell all my people I'm a Ridah. Nobody cries when we die, we Outlawz, let me ride...”
Between the bombastic street verbiage and scene setting, you get these raw, universal concepts from 2Pac. “I’d be a liar if I told you that I never thought of death.” He could be equally specific and broad at once, and with one of the best flows and delivery in the industry.
“Life goes on” for all of us. This is Tupac dealing with death, and soon the world would have to deal with his.

#049/420 - 2Pac, “Old School”

I don’t think you get a more excited sounding 2Pac anywhere else in his discography. Nothing too heavy, nothing too emotional, nothing too crazy, just 2Pac nerding out over hip hop and growing up in New York. It’s a real treat to hear this self-proclaimed thug get giddy over stick ball and coconut flavored Italian ices.
“Remember popping and locking to Kurtis Blow, the name belts and Scott LaRock the Super Ho back in Latin Quarters? When Slick Rick was spittin La Di Da Di, gaming the hoochies at the neighborhood block parties. I remember, breakdancing to Melle Mel, Jekyll and Hyde, LL when he Rocks the Bells. Forget the TV, I'd rather hit the streets and do graffiti. Be careful, don't let the transit cops see me. It ain't nothing like the old school.”
It’s gotta be my favorite from 2Pac, with my favorite hook and beat from any of his songs as well. And what was once remembering nostalgia, has become nostalgia itself. It reminds me of afternoons in my Chicago apartment looking out at Lake Michigan and Comiskey Park playing 2Pac albums on my old iMac.
2Pac was a phenomenon. If you have never seen the movie Tupac Resurrection, I also recommend it. It’s the only documentary I can think of about a deceased person that is narrated by the deceased person throughout the film as if he knew he was going to die. Had he lived longer, I could easily have seen him becoming an equivalent in rap to Bob Dylan. Maybe he was already with only 25 years to his life. Undoubtably a poet with many sides, “I came through the door, said it before. That was the SHIT!”
Next week, it’s someone rarely played back-to-back with Tupac. He’s known as the piano man and my dad was once confused for him at a hotel, it’s the one and only, William Joel.
420 to 30: A Music Retrospective
Week 2: The Jackson 5/The Jacksons
Week 3: A Tribe Called Quest
Week 4: Weezer
Week 5: Bob Dylan
Week 6: Led Zeppelin
View the full list of "420 Songs" here: https://tinyurl.com/y8fboudu (Google spreadsheet link)