The Insane True Story of Diddy and Tupac EXPLAINED
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VOICE OVER: Rebecca Brayton
WRITTEN BY: Nick Spake
It's time for a deep dive into this infamously contentious celeb relationship. Welcome to WatchMojo, and today we're exploring the history between Sean 'Diddy' Combs and Tupac Amaru Shakur. Our breakdown includes Part One: A Tale of Two Coasts, Part Two: Changes, and Part Three: Who Shot Ya?
The Insane True Story of Diddy & Tupac Explained
Welcome to WatchMojo, and today we’re exploring the history between Sean ‘Diddy’ Combs and Tupac Amaru[a] Shakur.
Part One: A Tale of Two Coasts
Before Diddy and Tupac were household names, there was already a longstanding feud between the East Coast and West Coast hip-hop scenes. Hip-hop can be traced back to the early 70s when it emerged from block parties in the Bronx. With the music genre rooted in New York, the East Coast scene prided itself on being the top dog. As the 80s transitioned to the 90s, though, the West Coast started to find its voice, becoming a formidable contender to the East Coast’s crown. Despite this growing rivalry, some called for unity. Near the turn of the decade, songs like “Stop the Violence” came from the East Coast while the West Coast echoed with “We’re All in the Same Gang.”
Tensions began to escalate in 1991 when Suge Knight, Dr. Dre, Dick Griffey[b], and D.O.C. founded the West Coast label, Death Row Records. With hit albums like “The Chronic” and “Doggystyle,” the West Coast was gaining the respect it had sought for so long. As the West Coast reached a turning point, so did the East Coast as Sean ‘Puffy’ Combs founded Bad Boy Records. Having recently been fired from Uptown Records, the artist who would soon be known as Diddy established himself as a music mogul, bringing on talent like Christopher ‘Biggie Smalls’ Wallace, aka The Notorious B.I.G. Despite being born in New York, Biggie spent some time in Los Angeles where he befriended another rising rapper named Tupac Shakur.
Introduced through a drug dealer, Biggie would crash on Shakur’s couch in California. Shakur also visited Biggie in New York. At one point, Biggie asked Shakur to be his manager. Shakur suggested he stick with Diddy, saying, “He will make you a star.” Regardless, their friendship wouldn’t survive the East-West rivalry. While in New York on November 30, 1994, Shakur dropped by Quad Studios with an entourage, including rapper Randy “Stretch” Walker. Confronted by three men in the lobby, Shakur was shot multiple times. Although it seemed like a robbery, Shakur grew suspicious when Diddy and Biggie arrived on the scene with James “Jimmy Henchman” Rosemond[c], the latter of whom had called him to Quad. Shakur became convinced that Bad Boy had set him up.
Following the shooting, Shakur was sent to prison for sexual abuse in early 1995. Diddy visited Shakur during his incarceration, claiming Bad Boy wasn’t behind the shooting. This did little to ease Shakur’s suspicions. The beef reached a boiling point in August 1995. After seeing Shakur in prison, Suge Knight headed to the Source Awards. Accepting Motion Picture Soundtrack of the Year, Knight threw shade at Diddy, who seemingly took the high road in another speech. Only a month after Knight received boos at the Source Awards, his friend Jai ‘Big Jake’ Robles [d]was murdered while leaving a birthday party. Knight blamed Diddy, who was also in attendance. After Knight secured his release from Rikers Island, Shakur officially joined the Death Row family.
Part Two: Changes
Whether or not Bad Boy was behind Shakur’s shooting, he was now the enemy. Shakur fired lyrical shots at Diddy, Biggie, and Bad Boy with his diss track, “Hit 'Em Up.” Some theorized that Biggie referenced Shakur in the song “Long Kiss Goodnight.” While war had been declared, Shakur didn’t come off as fazed. Having survived multiple shootings and incarcerations, a part of Tupac seemed to think he was invincible. Shakur’s luck ran out in Las Vegas on September 7, 1996. After getting into a fight with gang member Orlando ‘Baby Lane’ Anderson at the MGM Grand, Shakur headed to a nightclub with Suge Knight. At a stoplight, a Cadillac pulled up to their vehicle. Shots were fired with Shakur getting hit four times.
Six days later, Shakur died in the hospital. In February 1997, Diddy and Snoop Dogg - himself a West Coast artist - appeared on “The Steve Harvey Show” together. Both also held a press conference, pleading to end the rivalry between the East and West Coasts. Snoop said, “I don’t want to talk about yesterday. I want to talk about tomorrow. We’ve got to come together, shake hands, call for peace and move forward.” The violence didn’t stop, however. On March 9 that same year, Biggie was fatally gunned down in Los Angeles. With many believing Bad Boy assassinated Shakur, Biggie’s shooting was seen as retaliation. Tupac and Biggie’s deaths were the climax of the East-West rivalry with more artists calling for peace over the following years.
Part Three: Who Shot Ya?
Animosity between the East and West Coasts has died down since the 90s. With Tupac and Biggie’s murders going unsolved for years, though, a shadow of doubt continued to loom over both coasts. In a 2002 Los Angeles Times article entitled “Who Killed Tupac Shakur?,” investigative reporter Chuck Philips suggested that the shooter was Orlando Anderson, who died in 1998. Philips also implied that Biggie put a $1 million hit on Shakur, supplying the murder weapon. While Anderson and Biggie had denied involvement, the article renewed interest in the case. The LA Times retracted the article in 2008 after Diddy accused the outlet of falsely connecting him to Shakur’s death. Diddy stated, “It is beyond ridiculous and completely false,” calling the Times “irresponsible.”
Philips nonetheless stood by his statements until his death in January 2024. A year before Philips’ passing, the authorities seemingly reached a breakthrough in Shakur’s murder. On September 29, 2023, the Las Vegas Police arrested Duane ‘Keefe D’ Davis[e], Anderson’s uncle. It wasn’t the first time Davis’ name had come up in Shakur’s case. In 2011, LAPD detective Greg Kading, who had investigated Biggie’s murder, published a book alleging that Diddy offered Davis a cool million to take out Shakur and Suge Knight. While Davis had been on the authorities’ radar, the gang leader managed to avoid incarceration until he started openly talking about Shakur’s death. This included a 2019 tell-all memoir, which paved the path to his eventual arrest.
Davis’ trial is set to commence in March 2025. Despite Davis’ past claims that Diddy was involved, the Las Vegas Police have never considered him a suspect. Many doubt Diddy’s connection given the lack of evidence. Davis isn’t the most reliable or consistent witness either. Likewise, it’s difficult to back up the theories that Suge Knight ordered Biggie’s assassination. In any case, Diddy and Knight haven’t wiped their hands of any legal trouble. Following a hit-and-run in 2015, Knight was sentenced to 28 years in prison. Parole won’t be on the table until October 2034. Meanwhile, Diddy was arrested in September 2024 amid widespread accusations of abuse and sex trafficking. Over 100 have taken legal action against Diddy.
While Diddy is facing charges for his alleged history of sexual misconduct, that doesn’t mean people have forgotten about the Tupac conspiracy theories. Fellow rappers like Eminem, JID, and 50 Cent continue to point fingers at Diddy. Crime scene investigator Sheryl McCollum[f], who worked on Shakur’s case, also believes Diddy played a role. Tupac’s family has pushed to reopen the case, although his stepbrother Mopreme Shakur says “It’s not about [Diddy] specifically, it’s about justice for my brother.” That said, Mopreme doubted Diddy was “100 percent honest” when he denied involvement. Whatever future investigations uncover, Diddy survived longer than Tupac or Biggie. In this business, though, sometimes you either die a legend or live long enough to see yourself become the villain.
What are your thoughts on Diddy and Tupac’s history? Let us know in the comments.
[a]https://youtu.be/apj5WEfculw?si=vwWuhOuKQknuzvVf&t=21
[b]GRIFF-ee https://youtu.be/lEf8mAD1Pcg?si=TZ1u7nL-WK2p5YsL&t=26
dee oh see https://youtu.be/NyZLlngwHLw?si=tL8VRqeIDwPhLOV3&t=3308
[c]https://youtu.be/iyz6eoBneRI?si=HpYntMpucFNr1slB&t=22
[d]jye ROBE-lace @ 00:32:02 https://slate.com/culture/2020/02/transcript-of-slow-burn-season-3-episode-3.html
[e]keefy dee https://youtu.be/ExYhiNm9jvs?si=jTrAu23oknh4vS9M&t=99
KAY-ding
https://youtu.be/df56uM7Xvzk?si=vJrAJR431raMD0-A&t=16
[f]SHARE-ull muh-CALL-um https://open.spotify.com/episode/2OtAW0Ogpv1SrMdEDUldBL?si=43dbc1f1b35a4259
MOH-preem https://youtu.be/j8G-iISiNl0?si=x1V9mhrJKKryvHPv&t=148
Welcome to WatchMojo, and today we’re exploring the history between Sean ‘Diddy’ Combs and Tupac Amaru[a] Shakur.
Part One: A Tale of Two Coasts
Before Diddy and Tupac were household names, there was already a longstanding feud between the East Coast and West Coast hip-hop scenes. Hip-hop can be traced back to the early 70s when it emerged from block parties in the Bronx. With the music genre rooted in New York, the East Coast scene prided itself on being the top dog. As the 80s transitioned to the 90s, though, the West Coast started to find its voice, becoming a formidable contender to the East Coast’s crown. Despite this growing rivalry, some called for unity. Near the turn of the decade, songs like “Stop the Violence” came from the East Coast while the West Coast echoed with “We’re All in the Same Gang.”
Tensions began to escalate in 1991 when Suge Knight, Dr. Dre, Dick Griffey[b], and D.O.C. founded the West Coast label, Death Row Records. With hit albums like “The Chronic” and “Doggystyle,” the West Coast was gaining the respect it had sought for so long. As the West Coast reached a turning point, so did the East Coast as Sean ‘Puffy’ Combs founded Bad Boy Records. Having recently been fired from Uptown Records, the artist who would soon be known as Diddy established himself as a music mogul, bringing on talent like Christopher ‘Biggie Smalls’ Wallace, aka The Notorious B.I.G. Despite being born in New York, Biggie spent some time in Los Angeles where he befriended another rising rapper named Tupac Shakur.
Introduced through a drug dealer, Biggie would crash on Shakur’s couch in California. Shakur also visited Biggie in New York. At one point, Biggie asked Shakur to be his manager. Shakur suggested he stick with Diddy, saying, “He will make you a star.” Regardless, their friendship wouldn’t survive the East-West rivalry. While in New York on November 30, 1994, Shakur dropped by Quad Studios with an entourage, including rapper Randy “Stretch” Walker. Confronted by three men in the lobby, Shakur was shot multiple times. Although it seemed like a robbery, Shakur grew suspicious when Diddy and Biggie arrived on the scene with James “Jimmy Henchman” Rosemond[c], the latter of whom had called him to Quad. Shakur became convinced that Bad Boy had set him up.
Following the shooting, Shakur was sent to prison for sexual abuse in early 1995. Diddy visited Shakur during his incarceration, claiming Bad Boy wasn’t behind the shooting. This did little to ease Shakur’s suspicions. The beef reached a boiling point in August 1995. After seeing Shakur in prison, Suge Knight headed to the Source Awards. Accepting Motion Picture Soundtrack of the Year, Knight threw shade at Diddy, who seemingly took the high road in another speech. Only a month after Knight received boos at the Source Awards, his friend Jai ‘Big Jake’ Robles [d]was murdered while leaving a birthday party. Knight blamed Diddy, who was also in attendance. After Knight secured his release from Rikers Island, Shakur officially joined the Death Row family.
Part Two: Changes
Whether or not Bad Boy was behind Shakur’s shooting, he was now the enemy. Shakur fired lyrical shots at Diddy, Biggie, and Bad Boy with his diss track, “Hit 'Em Up.” Some theorized that Biggie referenced Shakur in the song “Long Kiss Goodnight.” While war had been declared, Shakur didn’t come off as fazed. Having survived multiple shootings and incarcerations, a part of Tupac seemed to think he was invincible. Shakur’s luck ran out in Las Vegas on September 7, 1996. After getting into a fight with gang member Orlando ‘Baby Lane’ Anderson at the MGM Grand, Shakur headed to a nightclub with Suge Knight. At a stoplight, a Cadillac pulled up to their vehicle. Shots were fired with Shakur getting hit four times.
Six days later, Shakur died in the hospital. In February 1997, Diddy and Snoop Dogg - himself a West Coast artist - appeared on “The Steve Harvey Show” together. Both also held a press conference, pleading to end the rivalry between the East and West Coasts. Snoop said, “I don’t want to talk about yesterday. I want to talk about tomorrow. We’ve got to come together, shake hands, call for peace and move forward.” The violence didn’t stop, however. On March 9 that same year, Biggie was fatally gunned down in Los Angeles. With many believing Bad Boy assassinated Shakur, Biggie’s shooting was seen as retaliation. Tupac and Biggie’s deaths were the climax of the East-West rivalry with more artists calling for peace over the following years.
Part Three: Who Shot Ya?
Animosity between the East and West Coasts has died down since the 90s. With Tupac and Biggie’s murders going unsolved for years, though, a shadow of doubt continued to loom over both coasts. In a 2002 Los Angeles Times article entitled “Who Killed Tupac Shakur?,” investigative reporter Chuck Philips suggested that the shooter was Orlando Anderson, who died in 1998. Philips also implied that Biggie put a $1 million hit on Shakur, supplying the murder weapon. While Anderson and Biggie had denied involvement, the article renewed interest in the case. The LA Times retracted the article in 2008 after Diddy accused the outlet of falsely connecting him to Shakur’s death. Diddy stated, “It is beyond ridiculous and completely false,” calling the Times “irresponsible.”
Philips nonetheless stood by his statements until his death in January 2024. A year before Philips’ passing, the authorities seemingly reached a breakthrough in Shakur’s murder. On September 29, 2023, the Las Vegas Police arrested Duane ‘Keefe D’ Davis[e], Anderson’s uncle. It wasn’t the first time Davis’ name had come up in Shakur’s case. In 2011, LAPD detective Greg Kading, who had investigated Biggie’s murder, published a book alleging that Diddy offered Davis a cool million to take out Shakur and Suge Knight. While Davis had been on the authorities’ radar, the gang leader managed to avoid incarceration until he started openly talking about Shakur’s death. This included a 2019 tell-all memoir, which paved the path to his eventual arrest.
Davis’ trial is set to commence in March 2025. Despite Davis’ past claims that Diddy was involved, the Las Vegas Police have never considered him a suspect. Many doubt Diddy’s connection given the lack of evidence. Davis isn’t the most reliable or consistent witness either. Likewise, it’s difficult to back up the theories that Suge Knight ordered Biggie’s assassination. In any case, Diddy and Knight haven’t wiped their hands of any legal trouble. Following a hit-and-run in 2015, Knight was sentenced to 28 years in prison. Parole won’t be on the table until October 2034. Meanwhile, Diddy was arrested in September 2024 amid widespread accusations of abuse and sex trafficking. Over 100 have taken legal action against Diddy.
While Diddy is facing charges for his alleged history of sexual misconduct, that doesn’t mean people have forgotten about the Tupac conspiracy theories. Fellow rappers like Eminem, JID, and 50 Cent continue to point fingers at Diddy. Crime scene investigator Sheryl McCollum[f], who worked on Shakur’s case, also believes Diddy played a role. Tupac’s family has pushed to reopen the case, although his stepbrother Mopreme Shakur says “It’s not about [Diddy] specifically, it’s about justice for my brother.” That said, Mopreme doubted Diddy was “100 percent honest” when he denied involvement. Whatever future investigations uncover, Diddy survived longer than Tupac or Biggie. In this business, though, sometimes you either die a legend or live long enough to see yourself become the villain.
What are your thoughts on Diddy and Tupac’s history? Let us know in the comments.
[a]https://youtu.be/apj5WEfculw?si=vwWuhOuKQknuzvVf&t=21
[b]GRIFF-ee https://youtu.be/lEf8mAD1Pcg?si=TZ1u7nL-WK2p5YsL&t=26
dee oh see https://youtu.be/NyZLlngwHLw?si=tL8VRqeIDwPhLOV3&t=3308
[c]https://youtu.be/iyz6eoBneRI?si=HpYntMpucFNr1slB&t=22
[d]jye ROBE-lace @ 00:32:02 https://slate.com/culture/2020/02/transcript-of-slow-burn-season-3-episode-3.html
[e]keefy dee https://youtu.be/ExYhiNm9jvs?si=jTrAu23oknh4vS9M&t=99
KAY-ding
https://youtu.be/df56uM7Xvzk?si=vJrAJR431raMD0-A&t=16
[f]SHARE-ull muh-CALL-um https://open.spotify.com/episode/2OtAW0Ogpv1SrMdEDUldBL?si=43dbc1f1b35a4259
MOH-preem https://youtu.be/j8G-iISiNl0?si=x1V9mhrJKKryvHPv&t=148
