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In the early 1990s, The Notorious B.I.G. and Tupac Shakur were great friends who formed a quick bond shortly after meeting. The rappers‘ friendship transcended music, as they genuinely regarded each other as brothers; their relationship, however, would deteriorate by the mid-1990s.

The Notorious B.I.G., who once gifted Tupac Shakur flowers and a gun, posing with Tupac Shakur
The Notorious B.I.G. and Tupac Shakur | Al Pereira/Michael Ochs Archives/Getty Images

Biggie Smalls and Tupac Shakur were good friends in the early ’90s

Tupac Shakur burst onto the scene at the turn of the 1990s when West Coast rap was dominating the world of hip-hop. He released his debut album 2Pacalypse Now in 1991, and soon transitioned to the big screen, starring alongside fellow music star Janet Jackson in the 1993 film Poetic Justice.

At the same time, The Notorious B.I.G. was a young crack dealer on the streets of Brooklyn who had a reputation in the neighborhood for having rap skills when he got on the mic at parties. His 1993 song “Party & Bulls***” signaled that a new rapper was on the rise, and Tupac himself was a fan of the song. The two eventually met on the set of Poetic Justice and quickly hit it off.

The Notorious B.I.G. brought Tupac flowers and a gun, and Tupac gave the flowers to Madonna

The 2022 book It Was All a Dream: Biggie and the World That Made Him explored Biggie and Tupac’s friendship, which included crashing on each other’s couches when they were in each other’s respective cities. Once, when Tupac was in New York and staying in a hotel, Biggie took his friend and future Junior M.A.F.I.A. groupmate Chico Del Vec to pay Tupac a visit.

“Yo, Chic, let’s go meet this n**** Tupac,” Big said. “We gonna go uptown. He in this hotel. I gotta link up with him to do this song. Go get the thing and come back.”

After he returned with a gun for Tupac, Big had an even stranger request. “Yo,” he said, “let’s get a bouquet of flowers and let’s get on the train.” 

When they got to the hotel, Tupac was flattered that Big brought him a bouquet along with a gun. “Yo, Big, you brought me flowers, man?” Shakur asked, to which Big responded, “I brought the flowers for you, man.”

Tupac was just as happy when Del Vec handed him a gun. “Oh, n****, this for me?!” he asked. 

“Yeah, something to hold you down, playboy,” Biggie responded.

Moments later, Del Vec heard a knock at the door, which turned out to be pop superstar Madonna. Del Vec couldn’t contain himself.

“Big’s telling me to chill. But she’s just smiling and she gives ‘Pac a kiss on the cheek and he gives her flowers. I was like, ‘Ohhhh snap!'” Del Vec recounted. “She left out the room and ‘Pac sat back down. I’m just sitting there in shock.”

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Madonna and Tupac’s relationship

Madonna revealed the truth about her and Tupac’s secret relationship in a 2015 interview with Howard Stern. Tupac ended their relationship with a letter written from jail in January 1995, explaining that his status as a revered icon in the Black community would suffer as a result of him publicly dating a white woman.

“For you to be seen with a Black man wouldn’t in any way jeopardize your career. But for me, at least in my previous perception I felt due to my ‘image’ I would be letting down half of the people who made me what I thought I was,” he wrote, according to TMZ. “I never meant to hurt you.”