It’s been over 20 years since Tupac Amaru Shakur passed away. While the New York-bred rapper, who came of age in the San Francisco Bay Area and is forever associated with his beloved Los Angeles, only lived to be 25 years old, the breadth of his creative work was staggering. When combined with his unique place in American pop culture—as a punching bag for politicians and, conversely, a revolutionary figure for those who felt in some way disenfranchised—that work has taken on a life of its own. The ripple effect of 2Pac’s life and career are still being felt and will likely help to shape hip-hop for decades to come.

As with any celebrity of his stature, there’s something innate and indescribable about what he meant and still means to people despite his short time in the music business. It can be difficult to pinpoint clear causes and effects for how a young man came to be such a Rorschach test for Americans in the 1990s and beyond. And given the consistency and sheer volume of his output, organizing Pac’s work into ‘best-of’ lists seems a futile task, unlikely to yield anything comprehensive or compelling, or anything that hasn’t been said before.

There are, however, other ways to consider his legacy, and to begin to explain just how and why he looms so large over our culture today, still making regular, plentiful appearances on T-shirts, city murals, and mixtapes around the world. What follows is a list of ten moments that helped cement Tupac as an icon. They span from 1991 until his death in 1996, and include songs, videos, guest appearances, movie roles, and even newspaper headlines. They’re the snapshots that come together to form the fuller picture we have of Tupac as a man and as an artist, a multi-talented prodigy who stood for something bigger than himself.