Like many people, you wish the first time had been a little different. You can't choose much in this life: your future favorite song comes on in an elevator while you're with three fat strangers and nobody you love, and that's what goes down in history.

Or you're crying on the curb outside a Wendy's on your very worst day of that whole year, while some methed-out lost cause from high school rolls by again and again, cruising the loop and making you hear every other thirty seconds of “Hypnotize.” And whichever boy it was that made you hurt and sent you running to the fast food parking lot will be lost to the sands of time, but the most kickass rapper in human history will be marked with and followed by that mood, like a pirate curse or invisible ink. It's like your stupid little sister always said—it's so random, and you'll never get another shot at discovering Biggie again.

For the rest of your life—when you're at the dentist, or too boozed up to drift off, or hitting every red light on the way to get your daughter from daycare—you’ll think about how you would have scripted it differently.

You could have learned Life After Death so many other, lovelier ways. Like lying on your bellies in your torn t-shirts sniffing Aidan's model railroad glue. Like parking by the river with Hailey Gunn and being gangster in the middle of a thunderstorm. So many gorgeous un-had moments. So many wasted, pissed-away, potentially perfect afternoons.

Instead, a week after you hear half of the one song, Daniel, your biology partner—all assholery and shiny acne—plays you the whole thing on his boom box while ignoring your DNA model and trying so hard to accidentally touch your ass. Oh, you don't know this shit yet? It's so boss. Let me lay some knowledge on you, baby girl.

You will always regret some things. The people who say they don’t are smug idiots, lying at least a little. You have begun to make peace with some of the things you know you couldn't or wouldn't have changed, like the neck tattoo that got you noticed but broke your mother’s heart. But you will never stop wishing you'd stood up off the curb and wiped your snot-face and run out and bought the album, taken it home that same day and read the glossy booklet while you ate Twizzlers (Cherry Twists) and nestled your head into the deep green carpet of your bedroom floor, drunk in each word, bass thump, and mic spit, everything sounding like the birth of the whole dirty old world.

Your favorite song from the album will continue to revolve over the years, of course, as it must, just like your favorite liquor and who you love—these things should not be static. “Hypnotize” to “Kick in the Door” to “Nasty Boy” to “Sky's the Limit.” You had your “Mo Money, Mo Problems” phase, certainly, but have come to believe it's a touch overrated. These days it warms your belly to dote on the looked-over tracks, the deep cuts and little-respected gems. Your therapist would have something to say about that, no doubt. You’re a sucker for a slow starter that grows on you with each listen.

For now, you believe with all your being that there's no better Biggie song than the twenty-first track from the worst disc of his best work. Lyrically, it's sort of a hateful thing, if you're honest with yourself. Puff Daddy guests, and he says he dates 'em like he hates 'em and treats 'em like he beats 'em, but it's so confusingly smooth. That melody carries a whole lot of sweetness inside it, hides a lot of the horror and hurt.

And you can't help but love that the first line of the song is the world is filled with pimps and hoes, but the title is just “The World is Filled . . .”

You take a bath. You take a lot of baths, let your mind wander, shave your legs with expensive cream. You have daydreamed that Daniel will die before you. Not that you want him gone—he's not a bad guy, but you could have done so much better and didn’t and won’t. You’ve dreamed that he'll go first and you'll spend the days after that with your music and the memories it drags along behind like tin cans trailing behind the getaway car squealing away from the wedding.

You can remember exactly where you were when the first plane hit the building, and also that you were listening to Tom Petty. Not Tom Petty and the Heartbreakers, just Tom all on his own. When you first heard “In Bloom” you were washing the dog, and you listened to all of In Utero—ten years too late—while chain-smoking menthol Basics and driving North to Seattle: how perfectly goddamn perfect. You've made love thirteen times while listening to The Wall, three of those on shuffle.

When you found out that Biggie died two weeks before Life After Death came out, you were standing in the grocery store trying to decide whether or not to steal a box of Ritz crackers while two girls gossiped the next aisle over. They thought the irony was hilarious, but you did not at all. Ha ha ha ha, one of them said, like an ugly horse, the last song on the album is called “You're Nobody (Til Somebody Kills You).” You have not forgiven those girls and you don't intend to.

You might have heard your favorite song for the first time in your best friend's basement, her hand darting out to flick the volume knob down every time her mom came down to change out the laundry just as a swear was coming. That might have been a good way, a good thing to be able to remember it by—really nice, but not sentimental or over-extravagant.

They never did make a video for that one, which makes you a little sad. So you just put on one of the others and mute it, soundtrack the thing yourself. The words don't match his mouth, of course, but so what? Whose do? The images still work. He's in a speedboat in the Florida Keys, where you always wanted to go and always didn't. He's at the barbershop, he's in a jail cell, his friend cannonballs into his private pool. It sure is, Biggie, you think. This world is so fucking filled.

—Eric Thompson