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This Day in Top 40 History: December 16

On Dec. 16, 2020, LeAnn Rimes was crowned the winner of season four of The Masked Singer. During the finale, the “Country Comfort” star, who had disguised herself as the…

Billie Eilish performs onstage during "Hit Me Hard And Soft" Album Release Listening Party at Barclays Center
Photo by Arturo Holmes/Getty Images

On Dec. 16, 2020, LeAnn Rimes was crowned the winner of season four of The Masked Singer. During the finale, the "Country Comfort" star, who had disguised herself as the Sun, blew the audience away with her fantastic rendition of "when the party's over" by Billie Eilish. The single, which was from Eilish's WHEN WE ALL FALL ASLEEP, WHERE DO WE GO? album, had cracked the Top 30 on Billboard's Hot 100.

Here are some other Top 40 history events from this day.

Breakthrough Hits and Milestones

Consider listening to these albums from Dec. 16:

  • 2008: The All-American Rejects launched their third studio LP, When The World Comes Down. The album delivered a couple of Top 40 hits, including the lead single, "Gives You Hell," which peaked at No. 4 on Billboard's Hot 100.
  • 2008: Jamie Foxx released Intuition, which featured guest vocals from Kanye West, Lil Wayne, and other big names. The album entered the Billboard 200 at No. 3 and sold slightly over 260,000 copies in its opening week. It also produced several successful hits, such as "Blame It," which reached No. 2 on the Billboard Hot 100 and No. 1 on the Hot R&B/Hip-Hop Songs chart. Another track that cracked the Top 40 on the latter was "She Got Her Own."
  • 2008: Keyshia Cole's third studio album, A Different Me, came out. It debuted at No. 2 on Billboard's 200 chart and sold over 320,000 copies in the first week. Additionally, the set produced a few Top 10 singles on the Hot R&B/Hip-Hop Songs chart, including "Trust," "Playa Cardz Right," and "You Complete Me."

Cultural Milestones

The music industry has hit several cultural milestones on this day:

  • 1981: Ray Charles was honored with a star on the Hollywood Walk of Fame. One of his most popular hits was "I Can't Stop Loving You," which ruled the Hot 100 for five weeks. His other Top 40 songs include "Hit the Road Jack" and "You Don't Know Me."
  • 1984: After seeing each other for about six weeks, "Boogie Woogie Bugle Boy" singer Bette Midler and Martin von Haselberg got married in Los Angeles, California. Unlike many celebrity marriages, the couple's union has lasted. Their daughter, Sophie von Haselberg, is known for playing Natasha on Jamie Denbo's "American Princess."
  • 2024: Billie Eilish took her Hit Me Hard and Soft: The Tour to Inglewood, California, where she performed at the Kia Forum. The tour supported her album of the same name. Notably, all tracks from Eilish's "Hit Me Hard and Soft" album charted in the Top 40 on the Billboard Hot 100.

Industry Changes and Challenges

Here are some of the changes and challenges this day has witnessed over the years:

  • 1997: Nicolette Larson died from liver failure at the age of 45. She was known for Top 40 hits, such as "That's How You Know When Love's Right" that featured Steve Wariner and "Lotta Love."
  • 2001: Stuart Adamson, Big Country's frontman, was found dead in a hotel room in Honolulu, Hawaii. According to the coroner's report, he died by suicide. Adamson was known for his song "In A Big Country," which was a Top 40 hit in the U.S. and the U.K.

From hosting album releases and tour stops to weddings and losses, Dec. 16 has certainly played its part in shaping Top 40 history.