20 years ago on Sept 7, 1996, something happened that would change music forever. Tupac Amaru Shakur was on top of the world at 25 years old. He was fresh out of jail, with a multi-platinum double CD (including two Billboard Hot 100 number one hits) and an aspiring movie career.

Tupac and his manager Suge Knight, CEO of Tupac’s label, Death Row Records were riding on the Las Vegas Strip after watching the Mike Tyson-Bruce Seldon fight. At one corner of the strip, a white cadillac pulled up and fired several shots at the car. Tupac was hit four times, and was taken to the University Medical Center in Las Vegas. He remained in a coma for six days until his death on September 13.

Five years later on August 25, 2001, Aaliyah Dana Haughton was also on top of the world at 22 years old. She had released a new self-titled album and had an aspiring movie career. She was growing into a superstar.

Aaliyah and her team were filming a music video for her song “Rock the Boat” in the Bahamas. They decided to leave a day early. A small plane picked them up. The plane takes off, but crashes a few minutes later. All people on board, including Aaliyah, were killed in the crash.

In the years that followed since the deaths of these iconic figures in music, it has been asked, what would they do if they were still alive today?

Would Tupac be working on music with fellow rappers such as Eminem and Kendrick Lamar?

Would Aaliyah be doing a collaboration album with Beyonce?

One thing that both Tupac and Aaliyah have in common was that they both shaped the music industry.

Tupac made it possible for rappers to get personal with their lives in their music with songs like “Dear Mama.” Aaliyah, despite being in her teens, showed us that age really is just a number, and paved the way for other singers such as Brandy, Monica, Beyonce and Rihanna.

It seems like a moment ago since both artists left us. They were in their prime, and it’s hard to say what would have happened if they were still alive today.   

Both artists were rising stars in the music industry. Tupac had several albums released before he died such as his controversial debut “2pacalypse Now “ His album “Me Against the World” debuted at number one on the Billboard 200, making him the first artist to have an album top the charts while incarcerated.

Tupac had several songs dealing with issues of black inner city youth such as “Brenda’s Got a Baby.” He also had several personal songs such as “Dear Mama” and “I Ain’t Mad at Cha.” He would also have several posthumous releases such as “Until the End of Time.” Aaliyah meanwhile, took the world by storm with her hit debut “Age Ain’t Nothing but a Number,” released when she was only 15 years old. Her sophomore hit “One In a Million”, took her to a whole new level, as she helped introduce a new sound in the music world.

Aaliyah also became the youngest female performer ever to perform at the Academy Awards in 1998, when she performed the song “Journey to the Past,” off the animated film “Anastasia”. Her hit single, “Are You That Somebody”, helped the “Dr. Dolittle” soundtrack go multi platinum. Her song “Try Again”, off the “Romeo Must Die” soundtrack, peaked at number one on the Billboard hot 100 based solely off radio airplay.

Both Tupac and Aaliyah were also rising stars in the film industry.

Tupac had three hit films: the classic hood drama “Juice” with Omar Epps, the street romance film “Poetic Justice” with Janet Jackson and the basketball film “Above the Rim” with Marlon Wayans.

By the time he died he had already finished three other movies: “Bullet” with Mickey Rourke, “Gridlock’d” with Tim Roth, and “Gang Related” with Jim Belushi. According to a 2014 Rolling Stone article, Tupac auditioned for the role of Mace Windu in the “Star Wars” prequels.

Meanwhile Aaliyah had a hit film, “Romeo Must Die,” with Jet Li. After that was completed she was filming the vampire movie “Queen of the Damned” which was released a few months after her death. She was also offered roles in the “Matrix” sequels, and even Whitney Houston offered her the lead role in the movie “Sparkle,” which was postponed mainly because of her death.

I can not say what both Tupac and Aaliyah would be doing today if they were still alive. My guess is they would be bigger stars than they were before. I believe Aaliyah would have been as big as Beyonce, possibly making music with her.

I also believe Tupac would have worked with artists like Kendrick Lamar, and perhaps would have reconciled with the Notorious B.I.G., if he were still alive. Both would also be A-List actors in mega blockbuster films. It’s possible that Tupac and Aaliyah could have starred in the “Barbershop” film series. Unfortunately, we will never know what they might have done. All we can do is honor their legacies, because legends never die.