20 Fun Facts About Billboard’s ‘Greatest Pop Star by Year’ Selections
Billboard's 'The Greatest Pop Star by Year (1981-2019)' project was a labor of love on the part of the entire staff. We thought you might be interested in some trivia based on the project. Here are…

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By now, you’ve probably had a chance to at least dip intoBillboard‘s‘The Greatest Pop Star by Year (1981-2019)’ project. It was a labor of love on the part of the entire staff.
We thought you might be interested in some trivia based on the artists who our staff selected as our year-by-year pop star MVPs. Here are 20 fun facts about them.
First artist to repeat as a year’s Greatest Pop Star: Madonna. The durable star earned the title in 1985 and again in 1989.
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Artist with the shortest gap between appearances as a year’s Greatest Pop Star: Janet Jackson. She repeated in 1993, just three years after first claiming the title.
Artist with the longest span of Greatest Pop Star rankings: Beyoncé. She first took the title in 2003 and took it again in 2014.
Youngest solo artist to rank as a year’s Greatest Pop Star: Britney Spears. The icon was just 18 when she took the title for 1999.
Oldest solo artist to rank as a year’s Greatest Pop Star: Beyoncé. The superstar turned 33 during the year of her second win in 2014. Runners-up:Jennifer Lopez andDrake, who were turned 32 while they led in 2001 and 2018, respectively.
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Only artist to rank as a year’s Greatest Pop Star both in a group or duo and as a solo artist: Justin Timberlake. He earned the title on his own in 2006. He had shared the title with his*NSYNC bandmates in 2000.
Only male artist to repeat as a year’s Greatest Pop Star: Timberlake. The other two-time winners, for whatever reason, have all been women–Madonna, Janet Jackson,Rihannaand Beyoncé.
Most recent group or duo to rank as a year’s Greatest Pop Star: ‘N Sync. The quintet took the 2000 title. Between 1981 and 2000, seven groups (Blondie,Bon Jovi,Nirvana,Boyz II Men,TLC,Backstreet Boys and *NSYNC) took the title, but starting in 2001, it’s been solo artists every year.
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Most No. 1 hits (1981-2009) by an artist who was never a year’s Greatest Pop Star: Phil Collins (7). Runners-up:Paula Abdul andBruno Mars (6 each).
Artists who were a year’s Greatest Pop Star but never had a No. 1 single on the Hot 100: Nirvana,Alanis Morissette and Backstreet Boys.
Only artist who was a year’s Greatest Pop Star but never had a top five single on the Hot 100: Nirvana. The trio’s highest-charting hit, “Smells Like Teen Spirit,” peaked at No. 6.
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Artists who were a year’s Greatest Pop Star but have not yet won a Grammy: Blondie, Backstreet Boys, ‘N Sync, Lopez,Katy Perry,Miley Cyrus
Artist who was a year’s Greatest Pop Star and has the fewest career Grammy nominations: Cyrus (1 nod). Runners-up: Blondie, Lopez (2 nods each)
Artist who was a year’s Greatest Pop Star who has won the mostGrammys: Beyoncé (24). Runner-up:Kanye West(21)
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Artist who was a year’s Greatest Pop Star who has received the most Grammy nominations: Beyoncé (70). Runner-up: West (69)
Artist who was a year’s Greatest Pop Star and has won the most MTV Video Music Awards: Beyoncé (26). Runner-up: Madonna (20)
Artist with the most MTV Video Music Awards who was not named a year’s Greatest Pop Star: Peter Gabriel (13). Runner-up:R.E.M. (12)
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Artists who were a year’s Greatest Pop Star and have won an Oscar: Prince,Eminem,Lady Gaga,Adele
Solo artists who were a year’s Greatest Pop Star and have died: Michael Jackson (died 2009),Whitney Houston (died 2012),George Michael (died 2016)
Members of groups that were a year’s Greatest Pop Star who have died: Kurt Cobain of Nirvana (died 1994), Lisa “Left Eye” Lopes of TLC (died 2002)
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