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Musical Artists with Top 40 Hits in the 80s, 90s, 00s, and 10s

There are only 5 artists that have had a song in the U.S. Billboard Top 40 in the four decades from the 1980s to the 2010s. See if you can name them.
Songs in italics are another artist's song that the artist was featured in.
Quiz by interopia
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Last updated: July 23, 2023
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First submittedSeptember 9, 2022
Times taken1,904
Average score40.0%
Rating3.83
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Genre
1980s
1990s
2000s
2010s
Musical Artist
Pop
Like a Virgin +18
Vogue +19
4 Minutes +8
Give Me All Your Luvin'
Madonna
Pop
Beat It +17
Black or White +9
You Rock My World +1
Don't Matter to Me +2
Michael Jackson
Rock
With or Without You +5
One +6
Beautiful Day +2
XXX
U2
Smooth jazz
Songbird +3
Forever in Love +5
Auld Lang Syne
Use This Gospel
Kenny G
Comedy
Eat It
Smells Like Nirvana
White & Nerdy
Word Crimes
"Weird Al" Yankovic
6 Comments
+5
Level 85
Sep 9, 2022
With only 7% of quiztakers getting the two lesser-guessed answers, I added the genres as hints.
+4
Level 59
Sep 17, 2022
The fact Weird Al has been popular for 4 decades now is crazy
+1
Level 39
Sep 20, 2024
He has also been trash for 4 decades
+2
Level 59
Oct 4, 2024
"He who is tired of Weird Al is tired of life."
+3
Level 62
Sep 17, 2022
Brilliant quiz idea; good one.