At the end of the 1990s, the music world was shaken when rap superstars Tupac Shakur and Biggie Smalls (commonly known as Notorious B.I.G. or simply Biggie) were gunned down approximately six months apart.

Both rappers were top artists for their respective record labels. Tupac Shakur led the sales charts for Death Row, while Biggie Smalls achieved similar success at Bad Boy. The murders coincided with the height of competition between the music brands they represented. To this day, numerous theories surround the cases, and the question “Who killed these two rappers?” remains a mystery.

Two Talented Black Artists

Tupac Shakur was of African American descent. His birth name was Lesane Parish Crooks, but in 1972, his parents decided to rename him after Tupac Amaru II, a Peruvian revolutionary executed by Spanish colonialists for leading an 18th-century uprising. His mother, Afeni, married his father, Billy Garland, an active member of the Black Panther Party in New York during the late 1960s and early 1970s.

Tupac Shakur was born into a family facing hundreds of charges related to “conspiracy against the U.S. government.” After his parents were imprisoned, Shakur struggled to support himself. He began studying acting, poetry, jazz, and ballet at the Baltimore School for the Arts. His talent emerged as he won several rap and beatbox awards and gained popularity at school for his humor and ability to connect with others.

Tupac Shakur, also known by his stage names 2Pac or Pac, quickly became a central figure in the competition for dominance in the West Coast rap scene during the 1990s. Notably, Shakur started his career as a backup dancer and MC for Digital Underground, a relatively obscure band at the time. He later gained fame as a revolutionary American rapper, musician, and actor, advocating against racial discrimination and violence.

Tupac became a “hit-making machine” for Interscope Records, producing numerous albums and songs that topped the charts. Tracks like “I Get Around,” “Keep Ya Head Up,” “2 of Americaz Most Wanted,” “God Bless the Dead,” and “Hail Mary” still resonate with young audiences. Albums such as All Eyez on Me (1996) and Greatest Hits (1998) established him as one of the best-selling music artists of his time.

By 2007, Tupac Shakur had sold over 75 million albums worldwide. Rolling Stone magazine ranked him 86th on its list of the greatest artists of all time. In April 2017, he was inducted into the Rock and Roll Hall of Fame. As for Biggie Smalls, he was born on May 21, 1972, and grew up in Bedford-Stuyvesant. His mother, Voletta Wallace, a Jamaican immigrant and teacher, raised him after his father abandoned the family when Biggie was young.

At age 12, the chubby young man began selling crack to street hustlers in his neighborhood. A few years later, he enrolled at Bishop Loughlin Memorial High School but, finding academics unappealing, turned to vocational training and eventually pursued drug dealing. At 17, he was imprisoned for nine months in North Carolina for trafficking crack.

In the late 1980s, Biggie’s life took a new turn when his exceptional rapping skills caught attention. He adopted the stage name Biggie Smalls, inspired by a character in the film Let’s Do It Again. Standing nearly 6 feet tall and weighing 140 kg, the name seemed fitting. At the time, his poetic style endeared him to many listeners.

To avoid legal entanglements, Biggie later changed his stage name to The Notorious B.I.G. He collaborated with the Bad Boy group 112 and pop icon Michael Jackson on the 1995 album History. Biggie also won numerous awards, including Rap Artist of the Year on the prestigious Billboard charts.

The Mysterious Deaths

It’s known that since 1993, Biggie met and befriended Tupac Shakur in Los Angeles, despite the fierce East Coast-West Coast rap rivalry. The two stars once signed contracts with Bad Boy. However, their friendship faded after Tupac was imprisoned for rape, while Biggie continued to rise in his career.

Tupac later joined Death Row. The rivalry between Death Row and Bad Boy escalated into a dangerous cycle of verbal feuds, physical altercations, and murder within a short period. This East Coast-West Coast hip-hop conflict spanned from 1991 to 1997.

The talents of Tupac Shakur and Biggie Smalls made them the opposing figureheads of their respective regions. When Tupac released songs with lyrics hinting at or threatening Biggie and Bad Boy, such as “Against All Odds” and “Bomb First,” Biggie retaliated with tracks like “Long Kiss Goodnight.”

The two were frequently compared in the media, and their fans engaged in heated debates for years. Then, unexpectedly, on September 7, 1996, at 11:15 local time, after leaving a Mike Tyson fight, Tupac’s car was stopped at a red light on East Flamingo Road and Koval Lane when an assassin in another vehicle fired four shots from a Glock into his chest, arm, and thigh.

He was rushed to the University of Southern Nevada hospital but succumbed to respiratory failure and cardiac arrest a few days later due to severe injuries. Shakur was only 25. Six months later, Christopher Wallace met a similar fate. After attending the 11th Soul Train Music Awards in Los Angeles, Biggie’s car stopped at a red light at the intersection of Wilshire Boulevard and South Fairfax when four shots were fired at him. The assailant was a Black man in a suit and tie driving a Chevy Impala. Despite immediate medical attention, Biggie died that night at age 24. However, a 2012 autopsy revealed he died from a single bullet that entered his right hip, pierced his organs, and lodged in his left shoulder.

“He cried a lot and was quite shocked after Tupac’s death. He might have feared he’d be the next target. Ultimately, he died a few months later,” his wife shared. The two deaths shared eerie similarities: both were shot by a Black man in a passing car, and both were key figures in the rival hip-hop factions with a longstanding feud.

Numerous Theories

More than two decades have passed, yet the identities of Tupac Shakur and Biggie Smalls’ killers remain unsolved. However, one thing is certain: these deaths are believed to be connected. Both were gunned down in cars, and at the time, Tupac and Biggie were embroiled in a showbiz rivalry. Several theories about the perpetrators have emerged.

One theory suggests Tupac and Biggie were unintended victims, with the real targets being the CEOs of their record labels. After Tupac’s death, police initially focused on Biggie Smalls as a suspect. But after Biggie was hit with four shots from a 9mm automatic, investigators turned to finding the shooter, suspecting that Death Row’s Suge Knight and Bad Boy’s Puffy Combs knew the culprit. Suge Knight, CEO of Death Row—where Tupac was signed at the time—was implicated in both cases. He appeared to have the strongest motive, with reports indicating he owed Tupac approximately $3 million.

On the night of Shakur’s murder, Suge Knight clashed with members of the Southside Crips gang at the MGM Grand casino. During the brawl, Tupac punched Orlando Anderson, a Southside Crips member. Rather than intervening, Knight made a suspicious phone call and insisted Tupac ride with him. First responders noted that both Shakur and Knight seemed to recognize their attacker.

Suspicion increasingly fell on Suge Knight, who had the most reasons to harm Tupac. However, since Knight was also injured in the shooting, police temporarily shelved their investigation into him. Six months after Tupac’s death, Suge Knight’s name resurfaced, with a theory that he colluded with corrupt police to kill Biggie in revenge. Russell Poole, a former Los Angeles police officer, proposed this idea, implicating corrupt officer David Anthony Mack, a former bodyguard for Suge Knight.

When Poole presented his theories to the police department, he was ordered to stop investigating, which only strengthened the speculations. Another conspiracy theory suggests that members of the record labels orchestrated the assassinations, believing that the deaths—especially of rappers entangled in legal and financial disputes with their companies—would generate more profit than if they remained alive.

More than 20 years later, these cases remain unsolved. Fans continue to mourn Tupac Shakur and Biggie Smalls, two extraordinarily talented individuals who left us too soon.