Aaliyah worked with record producers Timbaland and Missy Elliott for her second album, One in a Million; it sold three million copies in the United States and over eight million copies worldwide. In 2000, Aaliyah appeared in her first major film, Romeo Must Die. She contributed to the film's soundtrack, which spawned the single "Try Again". The song topped the Billboard Hot 100 solely on airplay, making Aaliyah the first artist in Billboard history to achieve this feat. "Try Again" earned Aaliyah a Grammy Award nomination for Best Female R&B Vocalist.

After completing Romeo Must Die, Aaliyah filmed her part in Queen of the Damned. She released her third and final album, Aaliyah, in 2001. On August 25, 2001, Aaliyah and eight others were killed in an airplane crash in The Bahamas after filming the music video for the single "Rock the Boat". The pilot, Luis Morales III, was unlicensed at the time of the accident and had traces of cocaine and alcohol in his system. Aaliyah's family later filed a wrongful death lawsuit against Blackhawk International Airways, which was settled out of court. Since then, Aaliyah's music has achieved commercial success with several posthumous releases. With album sales estimated to be between 24 to 32 million copies worldwide, Aaliyah has been credited for helping redefine R&B and hip hop, earning her the nickname "Princess of R&B".

Aaliyah Dana Haughton was born on January 16, 1979, in Brooklyn, New York. Born of African American and Native American descent, she was the second and youngest child of Diane and Michael Haughton. Enrolled at a young age for voice lessons by her mother, Aaliyah would perform at weddings, church choir and charity events. When she was five years old, her family moved to Detroit, Michigan, where she was raised along with her older brother, Rashad. She attended a Catholic school, Gesu Elementary, where she received a part in the stage play Annie in first grade. From then on, she was determined to become an entertainer. Aaliyah's mother was a vocalist, and her uncle, Barry Hankerson, was an entertainment lawyer who had been married to Gladys Knight. As a child, Aaliyah traveled with Knight and worked with an agent in New York to audition for commercials and television programs, including Family Matters; she went on to appear on Star Search at the age of nine. She then auditioned for several record labels and appeared in concerts alongside Knight at age 11.

After Hankerson signed a distribution deal with Jive Records, he signed Aaliyah to his Blackground Records label at the age of 12. Hankerson later introduced her to recording artist and producer R. Kelly, who became Aaliyah's mentor, as well as lead songwriter and producer of the album, which was recorded when she was 14. Released in June 1994, the album peaked at number 18 on the Billboard 200 and sold over three million copies in the United States. Aaliyah's debut single, "Back & Forth", topped the Billboard Hot R&B/Hip-Hop Songs chart for three weeks and was certified Gold by the RIAA. The second single, a cover of The Isley Brothers' "At Your Best (You Are Love)", peaked at number six on the Billboard Hot 100 and was also certified Gold by the RIAA. The title track, "Age Ain't Nothing but a Number", peaked at number 75 on the Hot 100. Additionally, she released "The Thing I Like" as part of the soundtrack to the 1994 film A Low Down Dirty Shame.

With the release of Age Ain't Nothing but a Number, rumors circulated of a relationship between Aaliyah and Kelly. Shortly after, there was speculation about a secret marriage with the release of "Age Ain't Nothing but a Number" and the adult content that Kelly had written for Aaliyah. Vibe magazine later revealed a marriage certificate that listed the couple allegedly married on August 31, 1994, in Sheraton Gateway Suites in Rosemont, Illinois. Aaliyah, who was 15 at the time, was listed as 18 on the certificate; the illegal marriage was reportedly annulled in February 1995 by her parents. The pair continued to deny marriage allegations, stating that neither was married.

In 1996, Aaliyah left Jive Records and signed to Atlantic Records. She worked with record producers Timbaland and Missy Elliott, who contributed to her second studio album, One in a Million. The album yielded the single "If Your Girl Only Knew", which topped the Billboard Hot R&B/Hip-Hop Songs for two weeks. It also generated the singles "Hot like Fire" and "4 Page Letter". The following year, Aaliyah was featured on Timbaland & Magoo's debut single, "Up Jumps da Boogie". One in a Million peaked at number 18 on the Billboard 200, selling over three million copies in the United States and over eight million copies worldwide.

Aaliyah attended the Detroit High School for the Performing Arts, where she majored in drama and graduated in 1997 with a 4.0 grade point average. Aaliyah began her acting career that same year; she played herself in the police drama television series New York Undercover. During this time, Aaliyah participated the Children's Benefit Concert, a charity concert that took place at the Beacon Theatre in New York. She contributed on the soundtrack album for the Fox Animation Studios animated feature Anastasia, performing a cover version of "Journey to the Past" which earned songwriters Lynn Ahrens and Stephen Flaherty a nomination for the Academy Award for Best Original Song. Aaliyah performed the song at the 1998 Academy Awards ceremony and became the youngest singer to perform at the event.

In 2000, Aaliyah landed her first major movie role in Romeo Must Die. A loose adaptation of William Shakespeare's Romeo and Juliet, Aaliyah starred opposite martial artist Jet Li, playing a couple who fall in love amid their warring families. It grossed $18.6 million in its first weekend, ranking number two at the box office. In addition to acting, Aaliyah served as an executive producer of the film soundtrack, where she contributed four songs. "Try Again" was released as a single from the soundtrack; the song topped the Billboard Hot 100, making Aaliyah the first artist to top the chart based solely on airplay; this led the song to be released in a 12" vinyl and 7" single. The music video won the Best Female Video and Best Video from a Film awards at the 2000 MTV Video Music Awards. It also earned her a Grammy Award nomination for Best Female R&B Vocalist. The soundtrack went on to sell 1.5 million copies in the United States.

After completing Romeo Must Die, Aaliyah began to work on her second film, Queen of the Damned. She played the role of an ancient vampire, Queen Akasha, which she described as a "manipulative, crazy, sexual being". She was scheduled to film for the sequels of The Matrix as the character Zee. Aaliyah went on to release her eponymous album, Aaliyah, in July 2001. Produced primarily by Timbaland, the album debuted at number two on the Billboard 200, selling 187,000 copies in its first week. The first single from the album, "We Need a Resolution", peaked at number 59 on the Billboard Hot 100.

On August 25, 2001, at 6:45 pm (EST), Aaliyah and various members of the record company boarded a twin engine Cessna 402B (N8097W) at Marsh Harbour, Abaco Islands, The Bahamas, to travel to the airport in Opa-locka, Florida, after they completed filming the music video for "Rock the Boat". They had a flight scheduled the following day, but with filming finishing early, Aaliyah and her entourage were eager to return to the United States. They made the decision to leave immediately. Against the advice of baggage handlers and the pilot, all the equipment from the shoot was loaded on to the plane. The group was unaware that the plane was unable to hold all the equipment of the Cessna 404 they had initially flown in by. Therefore, the aircraft exceeded the standard weight and balance tolerance limit provided by Cessna. The plane crashed shortly after takeoff, about 200 feet (60 m) from the runway. Aaliyah, pilot Luis Morales III, hair stylist Eric Forman, Anthony Dodd, security guard Scott Gallin, video producer Douglas Kratz, stylist Christopher Maldonado, and Blackground Records employees Keith Wallace and Gina Smith were killed.