The 1990s saw a significant rise in female rappers, the kind that hip-hop had never seen before. From Missy Elliott to Lil Kim and Foxy Brown, the culture began to embrace women, and one of the most prevalent was the actor and rapper Queen Latifah.

Latifah has been a juggernaut in the entertainment industry since her arrival, and before the turn of the millennium, she worked with several legendary MCs, many of whom have since become cultural heroes. One icon she worked with in the 1990s was none other than Tupac Shakur.

Not only were Shakur and Latifah collaborators, but they were also good friends. They rose to fame at a very similar time and made their first breakthroughs in the early ’90s, although they were both somewhat present in the late ’80s.

In the late 1980s, Shakur was a part of the Oakland hip-collective Digital Underground, alongside rappers including Shock G, Chopmaster J, and Kenny-K. Their big hit, ‘The Humpty Dance,’ hit the charts in 1989 — the same year Latifah released her debut album, All Hail the Queen.

While Latifah was releasing Nature of a Sista’ and Black Reign for her female audience on the East Coast, Shakur was releasing 2Pacalypse Now and Strictly 4 My N.I.G.G.A.Z on the West Coast. However, during the late 1980s, they were on the same label.

During an appearance on the Hot Ones podcast with host Sean Evans, Latifah reflected on her friendship with the late emcee, recalling, “Me and 2Pac were pretty much labelmates. I was signed to Tommy Boy Records. Digital Underground was signed to Tommy Boy Records. Initially, I took Treach on the road as my roadie. Treach went on to head Naughty By Nature, and 2Pac was pretty much a roadie with Digital.”

Latifah continued, “He became a rapper in the group and made up the Humpty Dance, and they made the song ‘The Humpty Dance,’ which 2Pac created the dance too, and it became a smash hit.”

The Order in the Court creator then unveiled that she and Shakur went on a wild night out together in the Bay Area. Speaking about how Tommy Boy set up a joint tour, Latifah detailed, “We toured together, so we went all across the country! I was in San Francisco doing a show. It was my first show over $10,000, which was a New Year’s Eve show at this cool gay club in San Francisco. I was like, ‘Yo, I’m here!’ So 2Pac came to the club with me. I was like, ‘Yo, 2Pac is in the building!’”

She even spoke about how Shakur embraced it, adding, “They went crazy in there! They were like, ‘Take off your clothes!’ He took his shirt off anywhere. We had so much fun. But that was like my brother and he’s the type of person if he loved you, if he was cool with you, he’d lay his life down for you. I miss him, and I love him. Good times. And we were probably high.”