Remember the Free iTunes Song of the Week? In the days before streaming, Apple would make one song a week available as a free download, and often, they became hits. Fifteen years ago today, the iTunes Free Song of the Week was a song that never hit number one but still ended up launching an award-winning career: “Love Song” by Sara Bareilles.

Ironically, Sara wrote the song after becoming frustrated with her record label, who kept on telling her they needed her to write a commercial hit. Speaking to Glamour, Sara said, “I felt invisible and unimportant and manipulated and all the things.”

“This song was my little stubborn ‘f**k you’…but [it] ended up opening all these doors for me,” she noted.

“Love Song” didn’t enter the Billboard Hot 100 until several months later, but after Sara and the song appeared in an ad for the music streaming service Rhapsody, it shot up the charts, eventually peaking at number four and spending 19 weeks in the top 10.

“Love Song” also earned Sara her first Grammy nominations, for Song of the Year and Best Female Pop Vocal Performance, on its way to selling four million copies.

While “Love Song” remains Sara’s biggest hit, it set her up for a career that’s taken some unexpected turns. In addition to being nominated for multiple Grammys — with one win — she’s also been nominated for Emmy awards for both acting and writing music for TV, not to mention multiple Tony Awards, including several for the Broadway musical she co-wrote and occasionally starred in: Waitress.

Today, Sara is starring in the second season of her Peacock comedy, Girls5Eva, for which she occasionally writes music, and is also appearing on Broadway in a revival of the musical Into the Woods.

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