‘I Guess’ is Kathy Iandoli’s battle cry of #shruglife. It’s everything that impresses us and unimpresses us—which could be one in the same given the day.

Full disclosure: I’m a cross-generational nightmare. I’m what you call a “Xennial,” which means I’m a displaced era wedged between Generation X and the older side of Millennials. So all of the cool ’90s shit that everyone currently sweats (or “jocks” as they said in my day), I was old enough to actually experience in real time. But I’m not so far detached from today that I think young people are trash. So I speak from a partial place of authority when I discuss this conversation topic. This photoshopped image is not only presumptuous, but is also pretty trash:

So, for anyone unaware of who’s who in this photo, we have Tupac Shakur with his arms around XXXTentacion and Lil Peep. Tupac was shot on September 7, 1996 in Las Vegas and died a week later on September 13, 1996 at the age of 25. Lil Peep died from a reportedly accidental drug overdose on November 15, 2017 at the age of 21. XXXTentacion was gunned down in his car on June 18, 2018 at the age of 20.

As I sit here and stare at the ages of all three of these young men who senselessly died in their twenties, I can’t help but marvel at how young ‘Pac was. Twenty-five. He’s considered by many—myself included—to be one of the most prolific rappers who ever lived. And while I was aware of his age at the time of his death, mentally (to me) he was, like, 47—the age he would actually have been had he lived to see today). And there’s the part of old lady me that wants to point my cane and be all, “These other two guys couldn’t hold a candle to ‘Pac!” But X and perhaps even Peep were “Tupac” to some kids, so I’m not going to comment with some bar-by-bar comparison. What I am going to comment on is the assumption that Tupac would’ve welcomed X and Peep to the “Pearly Gates.” Nah.

When Tupac once mused “I wonder if heaven got a ghetto…,” he was questioning where he would fit in the afterlife. It was a recurring theme throughout his work, which is why so many—once again, myself included—believed for so long that he faked his death and was in Cuba chillin’ with Assata. I’ve since ditched that theory. Sort of. Anyway, he had a fascination with death—something XXXTentacion and Lil Peep both share with him. However, there’s one key ingredient that was always seemingly missing from Tupac’s work: emotion. Chalk it up to toxic masculinity or living in an age where rappers had to be “hard,” but Tupac created lyrically poignant works that were devoid of any feelings, unless he was discussing his mother. Meanwhile, X and Peep crafted music that was drenched in the feels. You could take their songs and literally wring out the tears.

This is where the cosign collision would’ve happened.

Hip-hop artists who skew older struggle enough with acknowledging the new guard, just as much as the new guard struggles with finding any commonality with their OGs. It’s a combination of feeling rejected for their abstract identities that contradict everything that their predecessors stood for, coupled with the fact that they simply don’t identify with older rappers. They spend more time listening to rock music, hence the extension of that “modern-day rockstar” narrative that they all seem to have adopted. Rappers reflective of the Golden Era view hip-hop through a singular lens and argue that the new generation has diluted the art form entirely.

So to assume that Tupac—theoretically the paragon of what rap’s yesteryears entailed—would ever take two prime examples of today’s musical landscape under his wing is a disrespect to everyone involved. And I can see the fantasy scenario:

Peep and X walk up to the gates (maybe it took Peep a little while longer to get there, or he was waiting for X or something), and Pac is there smoking a Newport on the other side. He flicks it into a cloud and opens up the gates. “C’mon in,” he says in his gruff yet authoritative voice. And then he goes and introduces them to Biggie and probably Aretha since you know that woman was an angel on Earth and made a beeline straight to heaven. Then he puts his arms around them and shows them the ropes. BULL. SHIT.

You want accuracy? Here’s the real story:

X and Peep get to the gates, and there stands Kurt Cobain on the other side. He gently nudges the gates open with the toe of his dusty Converse Chuck Taylors. Peep’s eyes are like saucers and X has his head bowed with tears puddling into a cloud. Kurt puts his arms around them and they all walk away. And then, off to the side, we have Biggie and ‘Pac there side-eyeing them. See, in my dream, ‘Pac and B.I.G. made their peace, so when they see these two come in, they look at each other and ‘Pac whispers to Biggie, “Tight pants?” Biggie turns to ‘Pac, “Multicolored hair?” Then they laugh and walk back over to Big L and Prodigy and continue their game of cards while Freaky Tah and ODB make jokes and Sean Price talks shit.

Throw this whole photo away of ‘Pac with one arm around Peep as he mixes his Lean and one arm around X as he’s too busy checking his phone. This would’ve never happened on Earth and it never happened in heaven.

This is my Xennial story, and I’m sticking to it.

More by Kathy Iandoli: