In 1991, Michael Jackson made a surprise appearance at the Rose Bowl show in Pasadena, CA with a roster of talent that included Aretha Franklin, Stevie Wonder, and Luther Vandross.

Two years later, as Hip-Hop began to be accepted as mainstream by corporate entities across the world, the 1993 Superfest infused MC's with their traditionally R&B-laden roster of talent. Headliners included Bell Biv DeVoe (BBD), Sisters With Voices (SWV) and Silk, while acts like Shai, Gerald Levert, Big Daddy Kane, Tag Team, and MC Lyte were also featured in select cities.

During the tour's October 24, 1993 stop at Madison Square Garden, the Superfest became the site of one of the most iconic cyphers ever recorded. Featuring verses from The Notorious B.I.G., 2Pac, Big Daddy Kane, and Shyheim, the session was famously immortalized on Funkmaster Flex and Big Kapp's album, The Tunnel.

The Superfest was promoted by Al Haymon, who before transitioning to becoming a major power broker in boxing, controlled a large promotion of what at the time was referred to as, "urban programming." Whether it was pure instinct, or a realization that the tour was stopping in the birthplace of Hip-Hop, Haymon decided to make Big Daddy Kane more prominent on the bill.

"Al Haymon decided to switch it and make me the headliner for those last two shows," Big Daddy Kane recalls. "I had Shyheim on the road with me even though he was underage [and] Budweiser is an alcohol. Shaheem was 15 years old. I had to keep him in the dressing room. I couldn't let him wander around backstage."

Kane's DJ, DJ Mister Cee, told Kane that The Notorious B.I.G. wanted to come to the show, and he wanted to bring 2Pac along as he was in town shooting a movie.

Big mentioned to Kane that he wanted to get on stage. Halfway through the show, Kane called him up.

"I'm an MC," Kane says. "So at the moment, only thing on my mind was, 'Okay, what verse am I'm going to say to tear they ass up?' That was really the only thing that was on my mind at the moment. But afterwards, I thought, 'Hey man, it was beautiful.' I knew that Big was a dope MC, a good dude, and always showed Mister Cee love, so I wanted the best for him. And Pac was my man. When I saw him winning and now he's doing movies, I was so proud of him. I feel like I was blessed to have them two brothers on the stage with me."

Fat Joe, who had released his debut album, Represent, only months earlier, was in attendance, and hungry to be a part of history.

"I was in the front row … and all of a sudden, you see the whole crowd turn back looking at the entrance, like the tunnel, and it was ‘Pac and Big — and this was Juice ‘Pac,” Joe later told Angie Martinez in 2023.

Joe recalled being invited on stage, but due to time constraints, he never got to spit a verse.

"Big Daddy Kane might have saved me ’cause I would’ve did some bullshit," he said.

Without Mister Cee's decision to record the performance, the cypher would have surely become something of a folktale amongst Hip-Hop heads — especially when the souring of Biggie and 2Pac's friendship played out so publicly.

"I recorded that on cassette, then it eventually got transferred to vinyl and became probably one of the illest live Hip-Hop performances of all time," Mister Cee later recalled.

Be sure to check out Big Daddy Kane and special guest Funkmaster Flex on February 1 at City Winery in New York City. Buy tickets here.