Imagine Biggie Smalls if he were alive today, if that one bullet had whizzed by six inches from where it hit. It’s shockingly easy. Biggie would be 44 — younger than Jay Z, only a couple of years older than both members of Run The Jewels. He would almost certainly still be making music, though he probably wouldn’t be as prolific anymore. He would’ve absolutely had a reality show at one point, one that ran for a season or two on some cable network. He would have the same intricate web of friendships and resentments that every aging New York rapper has. He might’ve fallen out with Puffy at some point, but he would’ve patched things up after a while; everyone does. Maybe he would’ve dropped a bunch of weight and then gained most of it back. Maybe Busta Rhymes would’ve gotten him really into weightlifting around 2005. He probably wouldn’t have gone the mogul route that Jay did. He probably would’ve just kept rapping, the way Nas did. I picture him making a series of chart-dominating megahits up until, say, 2004 and then slowly fading from popularity after that. I picture him making a really good back-to-basics album at some point. I picture him being pretty funny on Twitter but also retweeting compliments too often. I picture him owning at least three leather baseball caps. I picture him being great, still, now.

Biggie Smalls, who was murdered 20 years ago today, is the greatest musical loss of his generation. I firmly believe this. There were peers who were arguably his artistic equals, people like Kurt Cobain and Tupac Shakur, but they were machines of self-destruction, and that impulse helped to fuel their artistry. It’s harder to imagine either of them getting their lives together and surviving. Biggie was destructive, certainly, and if he hadn’t gotten himself embroiled in that headline-dominating ’90s geographical rap feud, maybe he wouldn’t have been shot. And, sure, Biggie made “Suicidal Thoughts.” But for the most part, his music was about surviving and thriving when all the odds are against you. Other ’90s losses, people like Eazy-E or Brad Nowell or Jeff Buckley or Selena, would’ve done big things, but I can’t imagine them leaving the same impact that Biggie left in his few years in the spotlight.

Biggie was 24 when he died, and he was the best rapper on the planet. He might’ve been the best rapper who had ever lived. He might still be the best rapper who has ever lived. This is discussed all the time, and it still isn’t discussed enough. Think about when you were 24. (If you’re not 24 yet, imagine being just as incompetent and confused as you are today, but also imagine the rest of the world expecting you to have your shit together by now.) (If you are currently 24, look at your fucking self.) When I was 24, I got into a shouting match with my neighbors because I refused to stop letting my dog piss on their flowers. I ate fries for lunch every single day. I sometimes looked at Suicide Girls on my work computer until I got caught. I was a fucking idiot. And at the same age that I was out there blundering through the world, Biggie Smalls was the greatest rapper on the planet. And then he was dead.

And it’s not just that Biggie was a great rapper. He also changed the course of the genre. He changed what great rappers were expected to do. That combination of bone-hard street talk, larger-than-life money talk, movie-star charisma, canny pop instincts, and indisputable technical skill — nobody had even attempted that by the time Biggie mastered it. Jay-Z, once a sort of junior Biggie collaborator, rode that exact same combination to levels of fame that transcended rap, and he was never as good at it as Biggie was on his first album. Biggie would’ve made his Blueprint before Jay did. He would’ve made his Black Album before Jay did. He would’ve made his Vol. 3 before Jay did. Hell, maybe he did make his Vol. 3.

Life After Death, the Biggie album that came out after his death, isn’t as good as Ready To Die, the one that came out before he died. But it does suggest a talent that’s growing and adapting to a changing rap landscape. For me, the most intriguing glimpse into what could’ve been was “Notorious Thugs.” On that track, of course, Biggie teamed up with the surging Bone Thugs-N-Harmony, whose melodically tourettic flow was like nothing anyone had ever heard before. In 1997, it was like Bone Thugs were from another planet. (Three 6 Mafia had accused them of biting, but those early Three 6 records, great as they are, don’t sound like that.) Biggie didn’t do a Bone Thugs flow on “Notorious Thugs,” but he did adjust his flow, switching up his cadence so that it would wrap around the beat in a similar way. No other New York rappers were attempting anything like that at the time. None of the city’s rappers were looking at the music emerging from the middle of the country and attempting to reckon with it. Biggie was alone in that, and he made a great track out of that.

In the years after, the South and Midwest would play increasingly important roles in rap. And based on “Notorious Thugs,” I expect that Biggie would’ve been able to adjust to all of it. He would’ve been able to record songs with all the stars who emerged in the next few years, and it wouldn’t have sounded forced — the way it did when, say, Nas made “Quick To Back Down” with Lil Jon. (It’s a fucking travesty that we never got to hear Biggie on a Lil Jon beat. He would’ve done unspeakable things.) Part of the reason Jay stood out was that he adjusted, making music with people like Timabaland and figuring out non-boom-bap ways to put songs together. Biggie beat him to that. He beat everyone to that.

There is every possibility that, if Biggie were alive today, he’d still be making great music. (This also leads us into all sorts of Marvel Comics What If? thoughtstreams: Does Puffy become a star himself if he doesn’t dominate summer 1997 with a Biggie eulogy? Does the shiny suit era ever happen? Does a DMX emerge in rebuke? Does Jay ever become a megastar if he never gets a chance to fill the vacuum that Biggie left? Does Biggie, through sheer force of personality, keep New York rap on top for a few more years?) And today, the 20th anniversary of Biggie’s murder, seems like a good time to think about all that great music that we never got. It also seems like a good time to go back and listen to the great music that we did get.