Abe Beame does the blunts and brews thing, knocking that Wu-Tang.

My favorite moment on Ready to Die comes at the end of the “Fuck Me” interlude. Biggie and Lil Kim simulate sex on a chair in the studio. As the skit reaches its climax, Kim intentionally or unintentionally falls off. Biggie immediately apologizes, and the listener is struck by his sincerity and concern. A brief heartfelt exchange follows, and I’m confident the words “fuck you bitch” will never again be delivered with such affection.

This has nothing to do with cadence or an ear for beats. It has everything to do with why Biggie was the greatest of all time. It was about how he allowed brief glimpses of humanity, letting us see his true character without resorting to cheap emo bitching.

Of course, there are the ways to enumerate why Chris Wallace was the greatest, but I think it’s really about his intangibles. He was a natural, the type of phenom you hear about in other musical genres: one who came out the womb playing a coronet solo or riffing on an electric guitar—a talent we’ll never see again.

“Friend of Mine” is one of Biggie’s most subtle and brilliant songs. Whenever I’m getting into GOAT conversation, I inevitably ask people to name the five best and five worst Biggie songs. You’ll get an incredibly varied range of answers, and sometimes some people’s favorites are other’s least preferable. His catalogue is simply that tight.

But “Friend of Mine” is in the vicinity of the worst more often than not, dismissed by some as rare filler on “Ready to Die.”

“Friend of Mine” opens with three different subjects layered on top of one another. What sounds like a blowjob is interspersed with Lil Kim putting dudes on blast. Meanwhile, Biggie espouses his callous philosophy on fidelity. It’s brilliant in a perverse way. You could argue the blowjob — raw sexuality—is the subject that Big and Kim fight out in court. Both sides prosecute.

Big kicks it off with blistering energy. Frank White was great at phrasing, but he was better at intros –as Jay-Z can attest, every verse begins perfectly. And there are few better than, “When I’m fucking off gin/I’m invincible,” for a song in which he is selling his invincibility.

It’s Biggie at his most polished and indurate, world weary and suspicious, unable to let his guard down. The verse is cluttered with gangster posturing and accusing women of malicious internet, but we’re given an explanation in his last couplet: “Thug n**** till the end tell a friend bitch/Cuz when I like ya then you go and fuck my friend, bitch.”

Following a brief preamble reiterating his lack of love for the opposite sex, Big launches into a short fable which carries the rest of the song. Displaying a startling economy of words, Big pulls a chick on the corner alongside his friend, D out the window of a Mazda MPV. In no time at all, he has fucked the girl. Shortly thereafter, the girl is fucking with D. The part that gets me every time is when he says: “That’s my n**** D, damn he got G.”

It’s delivered as admiration, but there’s no question that a note of envy and hurt lingers. As if the girl asks him why he won’t commit, Big punctuates his point: “Now she’s fucking him and fucking me, see?” Biggie was quick to discuss his flawed physical appearance, his weight, his lazy eye. It always struck me as that classic defense mechanism: I’ll make fun of me before you can.

In the final verse, the tale turns cautionary, as Big beautifully sneaks in: “now I play her far like a moon play a star.” His fears and insecurities have been confirmed, and his response is to withdraw, smutting her out and practicing nihilism in his steady rotation of females and taunts. He even fucks her sister.

But Big really betrays himself with the constant need to justify his behavior. If he was truly the cold asshole he’s advertising, no explanation would be necessary, and “Friend of Mine” would sound like every other ode to promiscuity. It shows his heart; he’s not a bad guy but conducts himself in this manner out of necessity. It’s his reaction to a fucked up system.

I’m sure there are plenty of rappers who are cool off the mic, but for my money, none have lyrically conveyed the depth of their personality like Biggie. The omnipresent dash of humility, the distinctly human doubt, the uncertainty brought to a field dominated by aggression and pomp. When you listen to Christopher Wallace’s music, you feel like you know him. More importantly, you feel that he’s someone worth knowing. “Friend of Mine” is a song about experience, how it makes it’s mark on us and how we carry those scars with us throughout life. It’s sad, it’s honest, it’s Wallace at his best.

Download:
MP3: The Notorious B.I.G.-”Friend of Mine”