Following this upheaval, Aaliyah changed record labels, hooked up with producers Jermaine Dupri and Missy 'Misdemeanor' Elliott and recorded her follow up, the successful and critically-lauded "One in a Million" (1996). The album introduced the singer's new, more mature sound and focused on her undeniable talent and range, fusing hip-hop beats with R&B grooves in a way that harkened back to a younger Mary J. Blige. Although Aaliyah was managed by her parents, the teen singer's videos and appearances were marked by a non-overt sexuality that she carried with easy confidence. Remarkably, her sensual image was altogether natural, where such attempts at more adult fare by contemporaries like Brandy smacked of forced Lolita-like precociousness. In 1997, Aaliyah contributed her vocals to the animated feature "Anastasia", singing the Oscar-nominated theme "Journey to the Past" over the end credits, and subsequently on the Academy Awards telecast in March 1998. Her performance of that same song on a 1997 episode of "The Rosie O'Donnell Show" so impressed producers of the then-developing Broadway musical "Aida" that she was invited to audition. While Aaliyah didn't land that stage role, film would continue to offer her hit-making opportunities; she scored with the Grammy-nominated "Are You That Somebody?" from the "Dr. Dolittle" soundtrack in 1998.

Aaliyah's next film project "Romeo Must Die" (2000) not only featured her hit song "Try Again", but marked the singer's film acting debut. She starred opposite Jet Li in this modern day multicultural crime world reworking of Shakespeare's tragic romance, playing Trish O'Day, daughter of an African-American crime lord (Delroy Lindo) at odds with a rival Chinese gang whose allies include the vengeance-bent Jet Li. Soon Aaliyah and Jet Li's characters fall in love, much to the disapproval of their warring families. Aaliyah brought a crucial toughness and quiet grace to her role, making an auspicious film debut in this music-infused actioner. Her relatively mysterious real-life persona (routinely dodging age questions and nearly always donning sunglasses) made her transition to the screen all the more seamless, allowing the public to readily believe her portrayals, where an artist with a more realized personality would be less credible.

Landing a starring role in the Anne Rice adaptation "The Queen of the Damned" (2002) as the eponymous vampire royalty proved her acting career wasn't just a fluke. Aaliyah was subsequently cast in the back-to-back sequels "The Matrix Reloaded" and "The Matrix 3", set to have a small role in the former which would expand to a co-starring role in the latter and was also picked to head up the cast of the remake "Sparkle". The release of her long-awaited self-titled third album in 2001 spawned the hit "We Need a Resolution" and debuted at number two on Billboards album charts. Tragically, after filming the music video for the follow-up single "Rock the Boat" in the Bahamas on August 25, 2001, Aaliyah and eight others were killed when their plane crashed just moments after take off, cutting short a most promising film and music career.