On October 14, 2020, Post Malone dominated the Billboard Music Awards, taking home nine trophies, including Top Male Artist, Top Billboard 200 Artist and Top Rap Tour. In the years that followed, he expanded his musical horizons, collaborating with country superstars such as Beyoncé, Morgan Wallen and Dolly Parton.
Photo by Kevin Winter/Getty Images
His genre-spanning career reflects how much popular music continues to evolve. However, October 14 has a rich musical history that stretches far beyond one artist or one awards show.
From Michael Jackson’s first solo chart-topper and David Bowie’s influential album Heroes to Cardi B’s record-setting breakthrough, this date has delivered plenty of memorable moments. It has also marked major performances, celebrity milestones and the loss of influential musicians.
Here’s a look at the songs, artists and events that make October 14 an important date in Top 40 music history.
Breakthrough Hits and Music Milestones on October 14
Chart-topping singles and influential albums have helped shape popular music across generations. October 14 stands out for several notable releases and achievements.
1972: Michael Jackson Scores His First Solo No. 1
Michael Jackson’s song “Ben” reached No. 1 on the U.S. singles chart on October 14, 1972. The emotional ballad, recorded for the film of the same name, became Jackson’s first solo single to top the chart.
The success marked an important early milestone for the young singer, who was already gaining recognition as a member of the Jackson 5.
1977: David Bowie Releases Heroes
David Bowie released Heroes, his 12th studio album, in 1977. The record was the second installment in his celebrated Berlin Trilogy, following Low.
Its title track, “Heroes,” eventually became one of Bowie’s most acclaimed recordings. With its atmospheric production and enduring message of hope, the song remains a defining moment in his musical legacy.
2000: Christina Aguilera Tops the Billboard Hot 100
Christina Aguilera reached No. 1 on the Billboard Hot 100 with “Come On Over Baby (All I Want Is You)” in 2000.
The energetic pop single became her third chart-topping hit, further establishing her as one of the defining pop stars of the era.
2008: Ray LaMontagne Releases Gossip in the Grain
Singer-songwriter Ray LaMontagne released his third studio album, Gossip in the Grain, in 2008.
The collection included “You Are the Best Thing” and “Let It Be Me.” Blending soulful vocals with folk and roots influences, the album reached No. 3 on the Billboard 200 and No. 23 on the U.K. Official Albums Chart.
2016: Kings of Leon Reach No. 1 With WALLS
Kings of Leon released WALLS in 2016, earning their first No. 1 album on the Billboard 200.
The record also produced “Waste a Moment,” which spent four weeks atop Billboard’s Alternative Airplay chart. The achievement reinforced the band’s standing as a major force in alternative rock.
2017: Cardi B’s “Bodak Yellow” Continues Its Chart Reign
Cardi B’s breakout single “Bodak Yellow” began the second of three consecutive weeks at No. 1 on the Billboard Hot 100 in 2017.
The milestone made Cardi B only the second female rapper to top the chart with a solo song, following Lauryn Hill’s “Doo Wop (That Thing).” The achievement cemented Cardi B’s place in hip-hop history and helped launch her into superstardom.
Cultural Milestones in Music History
Music history is about more than chart positions and album releases. Birthdays, relationships, films and unexpected career turns also help tell the story of popular culture.
These October 14 milestones connect major artists to the wider entertainment world.
1978: Usher Is Born
Usher was born in Dallas, Texas, on October 14, 1978. Known for his smooth vocals, polished choreography and dynamic live performances, he went on to become one of R&B’s most successful artists.
The eight-time Grammy Award winner has earned 18 Top 10 hits on the Billboard Hot 100, including the No. 1 singles “Burn” and “U Remind Me.”
1996: Madonna Welcomes Daughter Lourdes Leon
Madonna and Carlos Leon welcomed their daughter, Lourdes Leon, on October 14, 1996, in Los Angeles, California.
The pop icon later expanded her family with five more children: Rocco Ritchie, David Banda, Mercy James, Stella and Estere.
2006: Taylor Swift Replaces Eric Church on Tour
Eric Church’s opening slot on Rascal Flatts’ tour came to an abrupt end in 2006 after he reportedly played too loudly and exceeded his allotted performance time.
An up-and-coming country singer named Taylor Swift took his place. The unexpected change became a memorable early chapter in Swift’s career, years before she emerged as one of the world’s biggest music stars.
2007: Tom Petty Documentary Premieres
The documentary Runnin’ Down a Dream premiered at the New York Film Festival in 2007.
Directed by Peter Bogdanovich, the film explored the career of Tom Petty and the Heartbreakers, tracing their rise and their lasting influence on American rock music.
2010: Alicia Keys and Swizz Beatz Welcome Their Son
Alicia Keys and Swizz Beatz welcomed their first son together, Egypt Daoud Dean, in New York on October 14, 2010.
The couple later welcomed another son, Genesis Ali Dean, in December 2014. Keys is also stepmother to Beatz’s three children from previous relationships.
2011: The Footloose Remake Hits Theaters
A new version of Footloose arrived in theaters in 2011, revisiting the story of a teenager who challenges a town’s ban on dancing.
The remake introduced the story to a new generation and featured an updated soundtrack that reached No. 14 on the Billboard 200.
2017: Kacey Musgraves Marries Ruston Kelly
Country singer Kacey Musgraves married fellow singer-songwriter Ruston Kelly on October 14, 2017.
The couple had met at Nashville’s Bluebird Cafe in 2016. Their marriage ended in divorce, which was finalized in September 2020.
Notable Recordings and Live Performances on October 14
Live shows give musicians the opportunity to bring their biggest hits to life in front of fans. October 14 has featured major concerts, celebrated tours and performances that revisited pop music classics.
2010: Guns N’ Roses Deliver a 28-Song Set in London
Guns N’ Roses performed at London’s O2 Arena on October 14, 2010, as part of their Chinese Democracy Tour.
The 28-song set included fan favorites such as “Sweet Child O’ Mine,” “Welcome to the Jungle” and “Mr. Brownstone.” The show showcased the band’s enduring appeal and the lasting popularity of its hard-rock catalog.
2017: The Weeknd Brings His Tour to Las Vegas
The Weeknd’s Starboy: Legend of the Fall Tour stopped at T-Mobile Arena in Las Vegas, Nevada, on October 14, 2017.
The Toronto-born singer performed more than 20 songs, including “I Feel It Coming” and “Can’t Feel My Face.” The concert highlighted his ability to blend contemporary R&B, pop and electronic influences into an arena-sized production.
2023: Madonna Launches the Celebration Tour
Madonna began her Celebration Tour in London in October 2023 after a three-month delay caused by a serious bacterial infection.
The tour celebrated four decades of her career, revisiting the songs and visual eras that helped establish her as one of pop music’s most influential performers.
2024: Sabrina Carpenter Covers Madonna’s “Material Girl”
Sabrina Carpenter brought her Short n’ Sweet Tour to Minneapolis, Minnesota, on October 14, 2024.
One of the night’s surprises was her cover of Madonna’s “Material Girl,” connecting a contemporary pop hitmaker with one of the genre’s most recognizable anthems.
Music Industry Losses and Challenges
Music history also remembers the artists whose lives and careers ended too soon. October 14 is associated with the deaths of several musicians whose work left a lasting mark on rock, country, soul and K-pop.
2006: Freddy Fender Dies at 69
Freddy Fender died in Corpus Christi, Texas, in 2006 at the age of 69.
Born Baldemar Huerta in 1937, Fender began playing guitar and recording music as a child. He later became a prominent figure in country and Tejano music, earning U.S. Top 40 hits that included the chart-topping “Before the Next Teardrop Falls.”
2011: Drummer Chuck Ruff Dies at 60
Chuck Ruff died in San Francisco, California, in 2011 at the age of 60.
The drummer contributed to Sammy Hagar’s albums Danger Zone and Street Machine. He also played on “Frankenstein,” the instrumental hit by the Edgar Winter Group that reached No. 1 on the Billboard Hot 100.
2012: B.B. Cunningham Is Killed at 70
B.B. Cunningham, a musician who had worked with Jerry Lee Lewis, was killed in a shootout in Memphis, Tennessee, in 2012. He was 70.
Cunningham was a member of the Hombres, whose song “Let It Out (Let It All Hang Out)” reached the Top 20 on the Billboard Hot 100.
2019: K-pop Star Sulli Dies at 25
Sulli, the South Korean singer and actress who rose to fame as a member of the K-pop group f(x), died by suicide in 2019 at the age of 25.
Her death prompted widespread mourning among fans and renewed conversations about mental health and the pressures faced by performers in the entertainment industry.
As a member of f(x), Sulli was part of a group that achieved major chart success in South Korea and helped shape the evolution of modern K-pop.
2025: Soul Singer D’Angelo Dies at 51
Michael Eugene Archer, better known as D’Angelo, died in New York in 2025 at the age of 51, according to reports.
The influential singer, songwriter and producer was associated with the neo-soul movement that reshaped contemporary R&B in the 1990s and beyond. His best-known recordings include “Brown Sugar” and “Lady,” both of which reached the Billboard Hot 100.
His distinctive sound and musicianship helped make him one of the most respected figures in modern soul music.
Why October 14 Matters in Top 40 Music History
October 14 offers a snapshot of popular music’s ability to change, surprise and endure.
Michael Jackson reached his first solo No. 1 with “Ben,” David Bowie released the influential Heroes, and Christina Aguilera added another chart-topper to her growing collection of hits. Decades later, Cardi B made history with “Bodak Yellow,” while Post Malone’s award-winning career reflected the increasingly fluid boundaries between musical genres.
The date also connects generations of performers, from Madonna and Guns N’ Roses to Usher, Taylor Swift, The Weeknd and Sabrina Carpenter.
Whether through a chart-topping single, a groundbreaking album, a memorable concert or an unexpected career turning point, these events demonstrate how music history continues to shape the sounds and stars of today.
From Cardi B making money moves to Michael Jackson singing about a pet rat, October 14 has delivered some unforgettable moments in Top 40 music history.