Think fast—what’s your favorite song? Is it an oldie but goodie from Motown or an 80s hair-band rock hit? Those may be the tunes you fall back on, but did they hit number one on the charts? If this burning question keeps you up at night, fret no more. We’re listing the longest-running number-one hits of the 20th century from Billboard’s Hot 100 chart, generally considered to be the music industry's definitive ranking of current hits. The date represents the first time each song reached number-one status.
"One Sweet Day” by Mariah Carey & Boyz II Men
Time at #1: 16 weeks beginning December 2, 1995
'90s powerhouse R&B tracks seem to dominate the charts. It only made sense that Mariah Carey, one of the most iconic songstresses of all time thanks to her stunning five-octave range, and one of the most popular male groups would collaborate during their peaks. “One Sweet Day” spent 16 weeks on top—a record that has never been topped, though it was tied more than 20 years later in 2017, by a little tune you may have heard called "Despacito."
"Candle in the Wind 1997" by Elton John
Time at #1: 14 weeks beginning October 11, 1997
Whether you’re a '90s kid or were an adult during this decade, you probably remember where you were when you found out that Princess Diana passed away. The world was devastated, the royal family was rocked, and the French government cracked down on paparazzi as a result of Diana’s tragic death. In response to her passing, Sir Elton John reworked his heart-wrenching 1974 song “Candle in the Wind” in tribute.
"Macarena-Bayside Boys Remix” by Los Del Rio
Time at #1: 14 weeks beginning August 3, 1996
Do you remember the somewhat bizarre dance that went along with this song? If you’re a '90s kid, you probably do. This catchy Latin tune could be heard everywhere and ended up also spending 14 weeks at the number-one spot. Side note: if you have fond memories of dancing the “Macarena” with your friends, don’t look up the lyrics.
“I’ll Make Love to You” by Boyz II Men
Time at #1: 14 weeks beginning August 14, 1994
You shouldn’t be surprised that Boyz II Men had numerous top hits throughout their heyday. The R&B group was known for consistently producing romantic ballads and slow jams that played on repeat everywhere. So, “I’ll Make Love to You” is one such song that spent a cool 14 weeks on the charts at number one.
“I Will Always Love You” by Whitney Houston
Time at #1: 14 weeks beginning November 28, 1992
Let’s just start by saying, unless you have the late, great Whitney Houston’s coveted range, you shouldn’t attempt to sing this song. Even Dolly Parton—the original artist who both wrote and sang this song—wasn’t the least bit insulted when Whitney Houston opted to cover it as part of the soundtrack for her movie The Bodyguard. The song was a monster hit and helped propel the movie's soundtrack to becoming one of the top-selling albums in history.
“The Boy is Mine” by Brandy & Monica
Time at #1: 13 weeks beginning June 6, 1996
Who doesn’t love a story about a love triangle? “The Boy is Mine” was a late '90s tune that focused on two women—R&B hit-makers Brandy and Monica—who fell for the same man. After a dueling vocal battle, they realize that the real villain isn’t “the other woman” but the philandering boyfriend. The two divas reunited for a follow-up song in 2012 titled “It All Belongs to Me”.
“End of the Road” by Boyz II Men
Time at #1: 13 weeks beginning August 15, 1992
We told you Boyz II Men dominated the 90s, didn't we? The group returns with another slow jam that was everywhere in 1992. Not only did “End of the Road” spend 13 weeks at number one, it earned the Grammy Award for Best R&B Song.
“Smooth” by Santana featuring Rob Thomas
Time at #1: 12 weeks beginning October 23, 1999
Santana, the band fronted by Carlos Santana, has been making funky jams since the 1970s. But just before the turn of the century, the group experienced a resurgence from collaborating with younger artists. It was a form of a crossover, but this time expanded into a younger generation of fans. "Smooth" combined Santana's Latin roots with Matchbox Twenty singer Rob Thomas's more rock-inflected background. The result was nothing short of a smash.
These are just a taste of the mega-hits from the 20th century. What might be most remarkable is that many of these records still stand today. Are you surprised that your favorite tunes aren't on the list? Are there other earworms you couldn't escape from that you want to hear again (or, perhaps, never hear again)? Let us know!