Tupac's Most Iconic Moments

Image via Columbia

Before Tupac was a world famous artist in his own right, he was hauling gear and wearing lycra as a roadie and backup dancer for Digital Underground. After the Oakland group’s celebrated Sex Packets album, they were asked to contribute a song to the soundtrack for the Chevy Chase-starring film Nothing But Trouble. That track, “Same Song,” would mark Pac’s introduction to the world. Even at the earliest stages of his development, he was magnetic.

For most of his first two solo albums, Tupac concerned himself with the acute and structural forces that conspire against Black Americans. But where some of his subject matter—police brutality, racist housing policy—fell on deaf ears in the white mainstream, “Brenda’s Got a Baby” cut through. The song tells the gut-wrenching tale of a 12-year-old girl who finds herself pregnant and without any prospects, showcasing Pac’s skill as a linear, empathetic storyteller.

Tupac’s first starring role in a feature film is, without question, the movie’s most divisive character. Omar Epps stars opposite Pac as Juice’s emotional center, with Pac pushing the coterie of friends closer and closer to the brink of criminality, then fully over the edge. Much of Pac’s music is about wrestling with these sorts of competing impulses, and his ability to bring the proverbial devil on the shoulder to life so effectively underscores how deeply he understood each side of the argument.

Tupac’s second album, Strictly 4 My N.I.G.G.A.Z., was released after the rapper had come under fire from Vice President Dan Quayle. (You can hear Quayle on the album’s second track, saying of 2Pacalypse Now, “There is absolutely no reason for a record like this to be published. It has no place in our society.”) But “Keep Ya Head Up” rises above the political fracas, surviving as a beautiful treatise on feminism, race, and poverty. At just 21 years old, Pac was untangling the threads that made his neighborhoods feel so hopeless and providing a road map for the years to come.

Playing opposite Janet Jackson, Tupac spends Poetic Justice showing the verve and tenderness that lives even in those who have seen life’s grimmest moments. Where Juice was gothic and bludgeoning, Poetic Justice was soft and subtle, a strong argument for Pac’s more sensitive side.  

In November 1994, 2Pac was robbed and shot in the lobby of a Manhattan recording studio. He was rushed to the hospital to undergo emergency surgery; only three hours later, and against doctor’s orders, Pac checked himself out of the hospital, only to show up in a wheelchair for a court appearance the following day.

2Pac’s performance as Birdie in Above the Rim reveals what made him such a great artist: his empathy for and nuanced understanding of humans in every walk of life. Where songs like “Brenda’s Got a Baby” and “Keep Ya Head Up” profile those who have been made vulnerable, Birdie in the hands of another actor would be contemptible to the point where he detracted from the film. But Pac finds the angles to make him immensely watchable and, at some points, even sympathetic.

In the aftermath of the Reagan era and the crack epidemic, drug addicts populated plenty of artistic work. Of course, most of these figures were crudely-drawn stereotypes. On “Dear Mama,” the heartfelt ode from his third album Me Against the World, Pac renders his mom in all her complex beauty: a revolutionary, a caretaker, a mentor, a saint. Me Against the World was Pac’s most personal album to date, and became the first record to top Billboard while its author was behind bars.

The clear dividing line in Tupac’s career is the eight-month prison sentence he served in 1995. Upon his release, which was bankrolled by Suge Knight, Pac got to work for Death Row. “California Love,” which featured not only new Death Row label mate Dr. Dre, but the legendary Roger Troutman, came complete with a blockbuster music video. Directed by Hype Williams, it was shot on the set of Mad Max Beyond Thunderdome and borrows much of its imagery. It stands as one of the most celebrated videos in all of hip-hop history.

Those who worked with Tupac after his release from prison often note that he would demand that an artist’s first take is what would make the final cut. Never was that ethos more fully captured than on The Don Killuminati: The 7 Day Theory. Released posthumously in November 1996, Pac’s final album is a an hour-long frenzy of defiance, paranoia, soul, and boundless energy, the kind which can only be captured for a few fleeting seconds. Though there’s no way Pac could have predicted the time and place of his demise, he understood that life is brief and precious and knew how to immortalize himself in each moment.