Michael Jackson Extends Hot 100 Presence into Sixth Decade with Posthumous Hit 'Chicago'

Michael Jackson has now charted a new song on the Billboard Hot 100 in every decade since the 1970s — a record no other artist has ever achieved. The milestone came when "Chicago," a track from his 2014 posthumous album *Xscape*, debuted at No. 30 on the chart dated June 6, 2026, according to KIRO 7.
The song racked up 10.7 million U.S. streams in a single week, a 30% jump from the week before, per Action News JAX. It marks Jackson's 52nd solo Hot 100 entry — spanning six consecutive decades.
Jackson first appeared on the Hot 100 in the 1970s. He then landed new entries in every following decade: 20 songs in the 1980s, 12 in the 1990s, 4 in the 2000s, and 4 in the 2010s. "Chicago" is his sole 2020s entry so far, according to WPXI. No other artist has pulled off this run of new chart entries across six straight decades.
The record is specific to *new* entries, not re-entries of old holiday hits. That makes it far harder to achieve. Many songs Jackson recorded decades ago had never previously charted, per WOKV. "Chicago" itself was recorded in 1999 but sat in the vault for years before its 2014 release.
Jackson recorded "Chicago" — originally called "She Was Lovin' Me" — at The Hit Factory in New York in 1999. Producer Timbaland later reworked it for the *Xscape* album in 2014. The song was never pushed as a single. It was a deep cut, quietly sitting in the catalog for years.
Then the 2026 biopic *Michael*, directed by Antoine Fuqua and starring Jackson's nephew Jaafar Jackson, hit theaters on April 24. The film has earned nearly $850 million worldwide, per Boston 25 News. Streams of Jackson's full catalog surged 146% globally. "Chicago" caught fire on TikTok and rode that wave straight onto the chart.
Here's the twist: "Chicago" was not on the biopic's official soundtrack. Hits like "Billie Jean" (No. 19) and "Human Nature" (No. 31) re-entered the chart because of the film. But "Chicago" climbed on its own, pushed entirely by streaming algorithms and short-form video clips, according to 97X Online.
The song also climbed to No. 10 on the Hot R&B/Hip-Hop Songs chart — Jackson's 36th Top 10 hit on that tally. For a song to qualify for the Hot 100 under Billboard's catalog rules, it must rank in the Top 50 and show clear growth. "Chicago" cleared that bar easily, per Power Orlando.
The chart milestone lands at a complicated moment. Netflix released *Michael Jackson: The Verdict*, a three-part docuseries, on June 3, 2026 — just three days before "Chicago" debuted. The series revisits his 2005 trial and has drawn sharply divided reactions online, per WSOC TV.
Some fans see the documentary as a counter-narrative to the biopic's celebratory tone. Others call it a distraction from the chart record. Either way, Jackson is dominating the cultural conversation. His estate is now expected to release more vault material, seeing proof that deep cuts can still break through, according to WHIO.
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