Biggie Smalls is the illest. It’s hard to believe 20 years have passed since The Notorious B.I.G. was gunned down in the streets of Los Angeles. While his murder remains officially unsolved, the presence and influence of the man born Christopher Wallace still looms large over hip-hop.

The game has changed significantly since Big’s passing. His career was born in a largely offline world. There was no blog game to build him up and later tear him down, no social networks to annoyingly promote his material—or let him embarrass himself. Big did it the old-fashioned way: word of mouth, radio spins, flossy videos, and a whole lot of talent.

Rising rapidly to the top of hip-hop’s food chain, he was multi-platinum by the time most rappers today are getting their first blog posts. Looking back, Big was incredibly mature and successful for a young 20-something who’d spent such a short time in the limelight.

While his talent and legacy are largely overshadowed by his insanely public beef with you-know-who, Big was arguably the best to ever do it. An astonishingly gifted and well-rounded MC, Biggie was the personification of the American dream. Overcoming the crack-filled streets of Brooklyn to become the undisputed King of New York (and quite possibly an entire genre of music), B.I.G. was a rapper who appealed to everyone. He could make us dance. He could make us laugh. He could make us want to rob someone. He was even a bit of a sex symbol.

But while he was a comedic genius and an impeccable storyteller, there was also a darker side to Christopher Wallace. A side trapped in a cloud of paranoia and preoccupied with death. In fact, much of his material was centered around dying young, violently and in a blaze of glory. Was his tragic death a self-fulfilling prophecy? We’ll leave that for others to debate.

Unfortunately, Big doesn’t have the extensive catalog that many of his revered peers boast; but he did leave us with two near perfect albums, a bevy of freestyles, and countless classic guest appearances. Oh, and a couple of posthumous hits too.

As we approach the 20th anniversary of Big’s death, Complex celebrates the music that was the crowning achievement of his life. We’ve dug deep to pull together the 50 Best Biggie Songs because we’ll always love Big Poppa, and you should too.

Written by Andrew Barber (@FakeShoreDrive)