20 Fun Facts About Billboard’s ‘Greatest Pop Star by Year’ Selections

By now, you’ve probably had a chance to at least dip into Billboard‘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.

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 and Drake, who were turned 32 while they led in 2001 and 2018, respectively.

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, Rihanna and 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.

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 and Bruno 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.

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 most Grammys: Beyoncé (24). Runner-up: Kanye West (21)

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)

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)