Michael Jackson’s Historic Winning Streak Continues Into A New Decade

BusinessHollywood & EntertainmentMichael Jackson’s Historic Winning Streak Continues Into A New DecadeByHugh McIntyre,Senior Contributor.Forbes contributors publish independent expert analyses and insights. Hugh McIntyre covers music, with a focus on the global charts.Follow AuthorJun 05, 2026, 08:00am EDTMichael Jackson becomes the first solo artist to debut songs on the Billboard Hot 100 in six different decades as "Chicago" launches on the tally. LANDOVER, UNITED STATES: American pop music star Michael Jackson sings 13 October 1988 at the Capital Center in Landover, Maryland. AFP PHOTO/Luke FRAZZA (Photo credit should read LUKE FRAZZA/AFP via Getty Images)AFP via Getty ImagesFor more than a month now, Michael Jackson's music has been riding an intense wave of renewed popularity on the Billboard charts. Streams and sales of his most popular works exploded in the week or two before his namesake biopic Michael arrived in cinemas around the world. Since then, as the movie has continued to bring in millions of dollars at the box office each week, Jackson's name has remained on dozens of rankings all around the planet. By now, many of the songs and albums that most listeners are familiar with have started to decline, but the late superstar manages an impressive feat. A decade and a half after his passing, Jackson collects a new smash on the Billboard Hot 100, and as he does, he makes history.Michael Jackson’s "Chicago" Lands on the Hot 100Jackson's song "Chicago" appears on the Billboard Hot 100 for the first time. The tune, which was released in 2014 on Jackson's posthumous compilation Xscape, has never been pushed as a single, and yet it starts inside the top 40 on the ranking of the most popular songs in America. This frame, "Chicago" launches at No. 30.Michael Jackson’s Run Continues Into a Sixth DecadeJackson has now scored 52 solo wins on the Billboard Hot 100. Billboard reports that as "Chicago...