Chicago

Album: Xscape (2014)
Charted: 26
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Songfacts®:

  • This was originally titled "She Was Lovin' Me" when Jackson first recorded it at New York City's Hit Factory in 1999. It was earmarked for his 2001 album Invincible but didn't make the cut.
  • According to CNN, Jackson recorded the song from a demo he received from New York songwriter Cory Rooney, who would go on to produce several of Jennifer Lopez's hit tunes, including "Jenny From The Block" and "Play." He instantly "fell in love" with it laying down the tune just days after hearing the demo.
  • The song eventually appeared on Jackson's second posthumous compilation album, Xscape, after L.A. Reid, the chairman of Epic Records, enlisted Timbaland to retool this and other cuts. Timbaland, who'd only talked with the King of Pop once on the phone, began by listening to the original source material and immediately decided to forgo the instrumental track, working with just Jackson's vocals.
  • Here are some other songs that namecheck the Windy City in the title:

    "Chi-Town" by The Cribs
    "Chicago" by The Devil Wears Prada
    "Chicago Is So Two Years Ago" by Fall Out Boy
    "Chicago (We Can Change The World)" by Graham Nash
    "The Night Chicago Died" by Paper Lace
    "Chicago" by Kate Voegele
    "Via Chicago" by Wilco
    "Jesus Just Left Chicago" by ZZ Top.
  • "Chicago" was originally released on May 5, 2014, as a promotional single for Xscape. It peaked at #50 on the Hot R&B/Hip-Hop Songs chart but failed to enter the Hot 100. However, the release of the biopic Michael in US theaters on April 24, 2026, triggered a massive streaming surge across Jackson's entire catalog. Because "Chicago" features prominently in the film, its streaming numbers climbed sharply, allowing the song to finally make its Hot 100 debut in late May 2026.

Comments: 1

  • Barry from Sauquoit, NyHere's one more 'Chicago' to add to the list:
    On August 13th 1957, Frank Sinatra recorded "Chicago" at the Capitol Records Studio in Los Angeles, California {at the same session he also recorded "All The Way"}...
    Exactly two months later on October 13th, 1957 it entered Billboard's Top 100 chart at position #84 {amazingly it was tied at #84 with 5 other songs; "Around the World" by Victor Young, "Farther Up the Road" by Bobby 'Blue' Bland, "I'll Remember You" by Patti Page, "Till" by Percy Faith, and "Rocking Pneumonia and the Boogie Woogie Flu" by Huey 'Piano' Smith & the Clowns}...
    The following week it was off the Top 100; but his "All The Way" debut at #78...
    Both songs were featured in his 1957 movie "The Joker Is Wild", which had its world premiere on September 26th, 1957 in New York City...
    R.I.P. Francis Albert Sinatra {1915 - 1998}.
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