1997: Death of The Notorious B.I.G.

• Diddy was a close associate of Biggie Smalls, who was murdered in a drive-by shooting in Los Angeles. The event marked a pivotal moment in hip-hop history and led to intense media scrutiny and speculation about the East Coast-West Coast rivalry. Diddy faced questions regarding his involvement in the surrounding tensions.

1999: Club Shooting Incident

• Diddy, alongside Jennifer Lopez, was involved in a shooting at a New York City nightclub. They were arrested after fleeing the scene. Diddy faced serious charges but was later cleared, although the incident tarnished his public image.

2001: Legal Issues with Bad Boy Records

• Several artists associated with Bad Boy Records, including Ma$e, The Lox, and Faith Evans, publicly criticized Diddy over contract disputes and issues regarding artist treatment. This led to a perception of Diddy as exploitative, with former artists discussing their struggles in interviews and documentaries.

2004: Lawsuit by a Former Employee

• A former employee of Diddy filed a lawsuit alleging wrongful termination and harassment. The details of the lawsuit painted a less-than-flattering picture of Diddy’s management style. The case was settled out of court, but it raised questions about workplace conduct within his organization.

2005: "Making the Band" Controversy

• The reality show "Making the Band," which Diddy produced, garnered both attention and criticism. Contestants often faced grueling challenges, and Diddy was known for his tough love approach. His infamous demand that contestants walk across the Brooklyn Bridge to fetch him cheesecake became a cultural reference point, but many questioned the ethics of his treatment of aspiring artists.

2015: Arrest During UCLA Incident

• Diddy was arrested after a confrontation with a football coach at UCLA, where his son was playing. Allegedly, he attacked the coach with a kettlebell. The incident was widely reported, and Diddy faced charges of assault and making terrorist threats. He later reached a plea deal with the authorities, but the incident added to his controversial reputation.

2016: Diddy's MTV VMA Speech

• During the MTV Video Music Awards, Diddy made a speech that was seen by some as tone-deaf. He attempted to unify hip-hop but faced backlash for not addressing issues of social justice more directly during a time of heightened awareness regarding racial tensions in the U.S.

2018: Allegations of Abuse by Cassie Ventura

• After Diddy and his longtime girlfriend Cassie Ventura ended their relationship, she publicly accused him of emotional abuse. The allegations included instances of controlling behavior and manipulation. Diddy denied these claims, but they added to the scrutiny of his personal life.

2019: Controversy Over Black Lives Matter

• Diddy faced criticism regarding his involvement with the Black Lives Matter movement. Some activists felt that his contributions were more performative than substantive, leading to debates about celebrity activism and accountability within the movement. Diddy later expressed a desire to do more but was still scrutinized for his past actions.

2021: Business Ventures and Accusations of Exploitation

• Diddy launched various business ventures, including a new vodka brand. However, he faced accusations of exploiting Black culture through his marketing strategies. Some critics argued that his businesses did not adequately support the communities they originated from, reigniting conversations about cultural appropriation and responsibility.

2022: Personal Life Turmoil

• Diddy’s personal life continued to be a source of media attention, particularly regarding his relationships and family dynamics. Rumors and speculation about his relationships often overshadowed his professional achievements, leading to discussions about his impact on the industry and the scrutiny faced by Black men in the public eye.

2024: Diddy Enterprise

• Diddy was indicted by the U.S. attorney for the Southern District of New York on charges of Racketeering Conspiracy,  Sex Trafficking by Force, Fraud, or Coercion, and Transportation to Engage in Prostitution. He is currently in jail and awaiting Trial.