He only lived 25 years, but Tupac Shakur's output was prolific, and his impact on hip-hop remains unmatched, over 20 years since his death in Sept. 1996. His lyrics reflected the highs and lows of black life on the streets and in the family home, told though stories with indelible characters, as well as through introspection, turning the mirror on himself. All this he gave us, with the wisdom of one who packed two or three lifetimes' worth of experiences into a couple short decades.

To this day, he remains one of music's most complex figures, revered for his passion for the black and oppressed, and the vibrant, poetic way in which he showcased their humanity, even as it was actively being erased. Still, Pac struggled with his own demons, and after becoming famous, had numerous run-ins with the law; he also launched a war that would rock hip-hop to its very core, a war most agree was unnecessary, one that cost hip-hop two of its most visionary voices.

His mysticism, born largely from his constant musings on death, remains in tact after his untimely demise, overshadowed only by his lasting charisma. Tupac was more than an artist — he was a force, and his short life was full of twists and turns that shaped who he was as a man, and ultimately impacted the artists and listeners who followed.

We've compiled some of the most pivotal moments in his life — moments that illuminated who he was a man and artist, that shined a bright light on his failings, even those that led to his tragic death.