Michael Jackson’s 'Chicago' Gives Him Hot 100 Entries in Six Decades

Cover art for Michael Jackson’s “Chicago,” a track from the 2014 posthumous album “Xscape.” The song debuted at No. 30 on the Billboard Hot 100, giving Jackson new chart entries in six decades and showing how streaming and short-form video can turn a deep cut into a new chart moment years later. (MJJ Productions/Epic Records)

Michael Jackson’s “Chicago” was not built like a comeback single.

It was not one of the untouchable 1980s records that never really left radio. It was not featured in the new biopic. It was not even a hit when it first surfaced in 2014 on the posthumous album “Xscape.”

That is what makes its new Billboard moment more interesting.

“Chicago” debuted at No. 30 on the Billboard Hot 100 chart dated June 6, making Jackson the first artist with new Hot 100 entries in six different decades, from the 1970s through the 2020s. The song also becomes his 52nd solo entry on the chart.

The numbers tell part of the story. “Chicago” drew 10.7 million official on-demand U.S. streams during the May 22-28 tracking week, a 30% jump from the previous week, according to Luminate data cited by Billboard and People. Under Billboard rules, older songs can enter the Hot 100 if they rank in the top 50 and show meaningful growth.

The rest of the story belongs to the way catalog now moves.

The “Xscape” version of “Chicago,” written by Cory Rooney, was produced by Timbaland and Jerome “J-Roc” Harmon. The song has found a new audience through streaming and TikTok at the same time Jackson’s catalog is benefiting from renewed attention around the film “Michael.” But the song’s rise is not a simple movie bump, as is not featured in the film.

That matters. The track’s path is less about a soundtrack push than a deep cut becoming newly legible to listeners who did not meet Jackson through radio, MTV, Motown specials or the first life of “Thriller.” They met the song through the modern discovery machine: fragments, algorithms, playlists, short videos and catalog curiosity.

Jackson’s best-known records have also moved in the same chart cycle. On the latest Hot 100, “Billie Jean” sits at No. 19, “Human Nature” at No. 31 and “Don’t Stop ’Til You Get Enough” at No. 43. Earlier this spring, six Jackson songs charted simultaneously, a reminder that the current surge is broader than one viral track.

Still, “Chicago” is the record that changes the chart history. It joins “Love Never Felt So Good,” featuring Justin Timberlake, and “Slave to the Rhythm” as Hot 100 entries from “Xscape.” But unlike “Love Never Felt So Good,” which was presented as a major posthumous single, “Chicago” has taken the long way around.

That long route is the point. Catalog used to move in predictable waves: anniversaries, reissues, documentaries, death, scandal, commercials and tribute performances. Those forces still matter. But in the streaming era, a song can wait in the middle of an album for 12 years and become new again because enough people finally hear the same few seconds at the same time.

For Jackson, whose career was built on controlling spectacle, the achievement lands differently. This is not the “Thriller” video changing MTV, the Motown 25 moonwalk resetting television or a blockbuster album forcing the industry to recalculate pop ambition. It is quieter, stranger and more modern: a non-single from the estate era entering chart history through the habits of listeners born long after his imperial run.

That does not make the record bigger than the classics. It makes the catalog harder to contain.

“Chicago” is not the reason Michael Jackson matters. It is proof that the machinery around his music keeps changing, and the music keeps finding its way back into the room.

Lauryn Hill to Receive Living Legend Icon Award at BET Awards

BET will honor Ms. Lauryn Hill with its Living Legend Icon Award this month.

The network announced Thursday that Hill will receive the award during the 2026 BET Awards. The show is scheduled to air June 28 from the Peacock Theater in Los Angeles, with Druski as host.

BET said the award honors artists who “mastered their craft and never let go of the culture.” The line could drift into award-show excess. For Hill, it lands close to the record.

Hill first became a generational voice with the Fugees, whose 1996 album “The Score” moved across hip-hop, soul, reggae and pop without sounding designed for any one lane. Two years later, “The Miseducation of Lauryn Hill” made her a solo force on terms almost no other artist could have demanded at the time.

Released in 1998, “The Miseducation of Lauryn Hill” blended rap, soul, gospel, reggae, live instrumentation and diaristic writing into a record that felt both intimate and public. It explored love, faith, motherhood, self-worth and Black womanhood. The album sold more than 10 million copies and became a model for artists who wanted reach without softening their point of view.

Connie Orlando, BET’s executive vice president of specials, music programming and music strategy, said Hill “never chased the moment; she has shaped it.”

“Her artistry redefined what was possible in our music and gave a generation permission to be fearless, spiritual, and free,” Orlando said in a statement.

The honor follows a rare televised appearance from Hill. In February, she returned to the Grammy stage for an In Memoriam tribute honoring D’Angelo and Roberta Flack, opening with “Nothing Even Matters” before moving through a broader tribute to two artists whose work helped shape the vocabulary of soul and R&B.

Hill has often been discussed through absence — the long wait for another studio album, the uneven touring history, the distance between public demand and the artist’s own terms. But the BET honor is a reminder that her legacy has never depended strictly on output.

It is defined by what that output changed.

“The Score” remains one of the defining albums of the 1990s. “The Miseducation of Lauryn Hill” remains a landmark in modern Black music. Nearly three decades later, Hill’s influence is still heard in artists moving between rap and melody, confession and critique, spirituality and edge.

That makes the Living Legend Icon Award less a coronation than a formal acknowledgment of what the music already settled.

Peabo Bryson, Voice Behind 'A Whole New World,' Dies at 75 After Stroke

Peabo Bryson appears in an undated photo posted to his official Facebook page. Bryson, the two-time Grammy-winning R&B singer known for “Beauty and the Beast,” “A Whole New World (Aladdin’s Theme)” and decades of romantic ballads, died Tuesday at 75, days after suffering a stroke. (Credit: Peabo Bryson/Facebook)

Peabo Bryson, the two-time Grammy-winning R&B balladeer whose voice moved from soul radio to Disney’s early 1990s renaissance without losing its foundation, died Tuesday evening, days after suffering a stroke. He was 75.

His family confirmed his death in a statement, saying it found comfort in knowing “how deeply Peabo was loved and how many lives were touched by his voice and his generous spirit.”

The announcement came after Bryson’s representative said Sunday that the singer had suffered a stroke and was under medical care. At the time, his family asked for privacy as he received treatment.

Bryson’s voice became part of pop memory through two of the most recognizable movie duets of the early 1990s. He won Grammys for “Beauty and the Beast,” performed with Celine Dion, and “A Whole New World (Aladdin’s Theme),” performed with Regina Belle. Both songs won best pop performance by a duo or group with vocal.

Those records made him part of childhood for millions. But R&B audiences knew Bryson long before animated films carried his voice into the pop mainstream.

Born Robert L. Bryson in Greenville, South Carolina, Bryson came through the Southern music circuit before becoming one of contemporary R&B’s premier male vocalists. His official biography says he got his start as lead singer of Al Freeman & The Upsetters and Moses Dillard & The Tex-Town Display before releasing his 1976 debut LP, “Peabo,” on Atlanta’s Bullet/Bang label.

His catalog includes “Feel the Fire,” “I’m So Into You,” “If Ever You’re in My Arms Again,” “Can You Stop the Rain” and “Tonight, I Celebrate My Love,” his duet with Roberta Flack.