Comparisons have been made between Aaliyah and Rihanna ever since the latter debuted with her debut album Music of the Sun in 2005. Rihanna has listed Aaliyah as an inspiration and it has been said that her fashion style was inspired by Aaliyah alongside Tupac Shakur and Bob Marley. In August 2014, Rihanna was seen in an ensemble that was believed to have been inspired by Aaliyah.
It was rumored in 2014 that Rihanna would play Aaliyah in her Lifetime biopic Aaliyah: The Princess of R&B after Zendaya dropped out of the film. During promotion of the film, Wendy Williams claimed that Aaliyah was a predecessor for both Rihanna and Beyoncé.