Lost 1999 Song Finally Cracks the Billboard Hot 100 27 Years Later

Nearly three decades after it was recorded, a long-shelved Michael Jackson song has finally become a Billboard Hot 100 hit.

For the Billboard Hot 100 for the week ending in June 6, Jackson’s “Chicago” debuts at No. 30, marking the first time the track has ever appeared on the chart. The achievement gives the King of Pop his 47th career Hot 100 entry and adds another unexpected chapter to the renewed commercial success sparked by the blockbuster Michael biopic.

What makes the chart debut particularly remarkable is the song’s unusual history. Although fans are only now embracing “Chicago” as a hit, Jackson actually recorded the track in 1999 during sessions for what would eventually become his 2001 album Invincible.

Originally titled “She Was Loving Me,” the song was written by Cory Rooney, who later recalled to biographer Damien Shields that Jackson loved the track immediately after hearing a rough demo.

According to Rooney, Jackson recorded the song at New York City’s Hit Factory during sessions that stretched across several weeks in the spring of 1999. The singer reportedly became so attached to the track that he meticulously worked through multiple vocal takes and personally assembled the final vocal performance.

Despite the enthusiasm surrounding the recording, “She Was Loving Me” never made the final track list for Invincible. Instead, the song remained unheard by the public for more than a decade.

Following Jackson’s death in 2009, Rooney revisited the recording, and the track underwent several revisions before producer Timbaland reworked it for Jackson’s 2014 posthumous album Xscape. By then, the song had been renamed “Chicago,” after its memorable opening lyric: “I met her on my way to Chicago.”

Even with the push surrounding Xscape, the song never reached the Billboard Hot 100 during its original release cycle. Its chart success has come 12 years later, fueled by a massive resurgence in interest surrounding Jackson’s catalog.

The renewed attention has been driven largely by Michael, the hit biopic chronicling Jackson’s life and career. Since the film’s release, multiple Jackson classics have surged across streaming platforms and charts worldwide, with songs like “Billie Jean,” “Human Nature,” “Beat It” and “Don’t Stop ‘Til You Get Enough” all returning to the Billboard Hot 100 earlier this year.

Now, one of the most surprising beneficiaries of that renewed interest is a song that fans never even heard during Jackson’s lifetime.

For a track recorded in 1999, shelved for years, released posthumously in 2014 and overlooked by the Hot 100 at the time, finally reaching the chart in 2026 is an extraordinarily rare feat.

Nearly 27 years after Jackson first stepped into the studio to record it, “Chicago” has finally become a bona fide Billboard Hot 100 hit.

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