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AALIYAH—TRY AGAIN
With a rising musical career since she was a teenager, Aaliyah Haughton got her first major movie role in Romeo Must Die. Praised for its futuristic production by her mentor, Timbaland, “Try Again” reached number one on the Billboard charts on the week of June 17, 2000. It was the first song ever to take the number one spot on the Billboard Hot 100 based solely on the strength of its radio airplay. Unfortunately, her untimely death in 2002 put an end to the megastardom that awaited the beloved 22-year-old singer. 
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LISA LOEB – STAY (I MISSED YOU)
Lisa Loeb released “Stay (I Missed You)” in 1994 as the lead single to Reality Bites. Loeb’s neighbor and friend, actor Ethan Hawke, submitted “Stay” to cast member Ben Stiller, who was directing the film’s soundtrack—the single landed Loeb a major record deal. However, her career never surpassed her smash single, but we will forever revere her as one of the queens of Gen X.
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WHITNEY HOUSTON – I WILL ALWAYS LOVE YOU
It was a song that defined the 90’s. Originally written by Dolly Parton, Houston Whitney Houston adapted the song her first feature film, The Bodyguard. The single spent 14 weeks at number one on the Billboard Hot 100 chart and is one of the best-selling singles of all time. Out of all of her career hits, “I Will Always Love You” surpassed her previous record of three weeks at number one in 1986. The song remains as the longest-running number-one single from a soundtrack album