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Old School Archives

When Tupac Shakur and Biggie Smalls freestyled on stage together

There isn’t much left to tell about the tragic feud of Tupac Shakur and The notorious B.I.G. It was a pivotal battle in the world of hip hop that left both men dead and a music scene without their driving creative forces. To make matters worse, the beef shared between the two men had originally been a scene of the two rappers breaking bread with one another.

While it seems inconceivable that these perceived arch-enemies were confidantes, once upon a time, they were as thick as thieves. Pac was one of Biggie’s most trusted allies and someone whose opinion he held in the highest regard, even wanting to leave him in charge of his entire career. If it wasn’t for Tupac declining his request, then things could have ended up very differently. There’s no better assertion of this friendship than when the dup shared the stage with one another in Big’s hometown of New York City.

Taking place on October 24th, 1993, at the Budweiser Superfest in Madison Square Garden, Tupac Shakur and Biggie would share the stage and deliver a fiery freestyle battle. It would not only provide us with a nostalgic tableau of what could have been but also give the Brooklynite Biggie a taste of stadium-sized fame.

By 1993, Tupac was already becoming a name in hip hop. The naturally charismatic figure had been trying to inch his way into the music business ever since he could remember and was starting to reap the rewards of his hard work. Given the opportunity of a huge stage like MSG, Shakur made sure to open up the chance at such a large crowd to his nearest and dearest, including Big.

The duo had met earlier in the year while Shakur was filming Poetic Justice. While on the set, Biggie had heard Shakur playing his current hit ‘Party & Bullshit’ on repeat and was touched by his admiration. Tupac invited the NYC native to a party at his house and they instantly bonded. They would each stay at the other’s house when on the opposite coast and they appeared to be firm friends.

At the end of that year they cemented their friendship with this mega performance for Biggie’s home crowd. Via the audio below, we can tell just how much this meant to both men as they deliver fearsome freestyles. However, there can be no doubt that it is Biggie Smalls who not only wins the battle but arguably the crowd in its entirety too.

Only a year later the two men would be pitted against one another in an apparent attempt to kill the rap careers of each coast of America. It would be a beef that would cause casualties on both sides and, eventually, lead to both icons passing far too soon. Below, however, we get to witness a more serene moment, when they shared the stage, the mic and friendship.