Prince, Madonna, and Michael Jackson were born within three months of each other in the middle of 1958. (Kate Bush was also born during this time period.) During the ‘80s, they redefined the way we consume pop music, and the cults they spawned predicted the rabid fandom that we see around most current pop superstars. Ranking their singles together just made sense, as both a critical exercise and an expression of masochism.

A note on criteria: The songs on this list must have been commercially released as a single in the U.S. unless a video was produced that played in the U.S. and/or the song charted within the Top 40 of the Billboard Hot 100 or the Billboard R&B/Hip-Hop Songs chart. Songs on which one of the three artist in question sang prominent lead vocals in the verses and/or chorus qualified.

220. Madonna “American Pie”

219. Prince with Zooey Deschanel “Fallinlove2nite”

218. Michael Jackson with Paul McCartney “The Girl Is Mine”

217. Prince with Sheena Easton “The Arms of Orion”

216. Prince “Dinner with Delores”

215. Madonna “Hey You”

214. Michael Jackson “Ghosts”

213. Prince “Screwdriver”

212. Prince “Guitar”

211. Prince & 3RDEYEGIRL “Pretzelbodylogic”

210. Prince & 3RDEYEGIRL “Fixurlifeup”

209. Prince “Musicology”

208. Prince “Breakdown”

207. Prince “The Holy River”

206. Prince “The Work, pt. 1”

205. Prince “Fury”

204. Prince “S.S.T.”

203. Michael Jackson “Music & Me”

202. Michael Jackson “HIStory”

201. Madonna “This Used To Be My Playground”

200. Michael Jackson “Blood on the Dance Floor”

199. Michael Jackson “Ain’t No Sunshine”

198. Prince “Breakfast Can Wait”

197. Madonna “Hollywood”

196. Prince “Dance 4 Me”

195. Madonna “Hanky Panky”

194. Madonna “Miles Away”

193. Prince “Future Baby Mama”

192. Michael Jackson “Hollywood Tonight”

191. Michael Jackson “Cry”

190. Michael Jackson “Got to Be There”

189. Michael Jackson “Childhood”

188. Prince “Partyman”

187. Madonna “Love Don’t Live Here Anymore”

186. Michael Jackson “Behind the Mask”

185. Madonna “Revolver”

184. Prince “Te Amo Corazón”

183. Michael Jackson “Rockin’ Robin”

182. Prince “Purple Medley”

181. Prince “The Truth”

180. Madonna “American Life”

179. Prince “Cinnamon Girl”

178. Prince “F.U.N.K.”

177. Michael Jackson “Black or White”

176. Michael Jackson “Heal the World”

175. Madonna “Girl Gone Wild”

174. Prince “Just As Long As We’re Together”

173. Michael Jackson “With a Child’s Heart”

172. Michael Jackson “One Day in Your Life”

171. Prince “Glam Slam”

170. Prince “Peach”

169. Madonna “Nothing Really Matters”

168. Michael Jackson “Just a Little Bit of You”

167. Madonna “Don’t Cry for Me Argentina”

166. Prince “The Greatest Romance Ever Sold”

165. Madonna “You Must Love Me”

164. Michael Jackson “Touch the One You Love”

163. Prince with Angie Stone “U Make My Sun Shine”

162. Madonna with Britney Spears “Me Against the Music”

161. Prince “Gold”

160. Michael Jackson “Liberian Girl”

159. Michael Jackson “You Are Not Alone”

158. Prince “Extraloveable”

157. Madonna “Causing a Commotion”

156. Michael Jackson “One More Chance”

155. Madonna “You’ll See”

154. Prince & the Revolution with Apollonia “Take Me With U”

153. Madonna “Beautiful Stranger”

152. Prince “The Most Beautiful Girl in the World”

151. Michael Jackson “Jam”

150. Prince & the NPG “My Name Is Prince”

149. Madonna “What It Feels Like for a Girl”

148. Prince and the Revolution “America”

147. Madonna “Give Me All Your Luvin” (with Nicki Minaj and M.I.A.)

146. Madonna “Gambler”

145. Prince & the NPG “Money Don’t Matter 2 Night”

144. Madonna “Turn Up the Radio”

143. Prince with Nona Gaye “Love Sign”

142. Prince “Call My Name”

141. Michael Jackson “Leave Me Alone”

140. Prince & the NPG “7”

139. Madonna “Don’t Tell Me”

138. Michael Jackson “Gone Too Soon”

137. Prince “Why You Wanna Treat Me So Bad?”

136. Michael Jackson “Earth Song”

135. Madonna “Celebration”

134. Prince “Still Waiting”

133. Madonna “I’ll Remember”

132. Prince “Let’s Work”

131. Michael Jackson “This Is It”

130. Madonna “Give It 2 Me”

129. Madonna “Love Profusion”

128. Prince “New Power Generation”

127. Prince “Space”

126. Madonna “Nothing Fails”

125. Madonna “The Power of Good-Bye”

124. Michael Jackson “A Place With No Name”

123. Prince “When 2 R in Love”

121. Prince and the Revolution “Anotherloverholenyohead”

120. Madonna “Ray of Light”

119. Michael Jackson “Beat It”

118. Prince “Scandalous”

117. Michael Jackson “Bad”

116. Prince “Betcha By Golly Wow!”

115. Madonna “Rescue Me”

114. Michael Jackson “You Can’t Win”

113. Prince & the NPG “Cream”

112. Madonna with Jellybean and Catherine Buchanan “Sidewalk Talk”

111. Michael Jackson “We’re Almost There”

110. Madonna “Sorry”

109. Prince “Letitgo”

108. Madonna “Human Nature”

107. Prince “Eye Hate You”

106. Madonna “Die Another Day”

105. Madonna “Jump”

104. Prince & the NPG “Damn U”

103. Michael Jackson with Diana Ross “Ease on Down the Road”

102. Michael Jackson “Farewell My Summer Love”

101. Madonna “La Isla Bonita”

100. Madonna “Fever”

99. Prince “Delirious”

98. Michael Jackson “The Way You Make Me Feel”

97. Prince and the Revolution “Mountains”

96. Madonna with Massive Attack “I Want You”

95. Prince & the NPG “The Morning Papers”

94. Michael Jackson “Man in the Mirror”

93. Madonna “Burning Up”

92. Michael Jackson with Rockwell “Somebody’s Watching Me”

91. Prince “Let’s Pretend We’re Married”

90. Madonna “Rain”

89. Madonna “Take a Bow”

88. Prince “Batdance”

87. Prince “I Wish U Heaven”

86. Prince “Black Sweat”

85. Madonna with Justin Timberlake and Timbaland “4 Minutes”

84. Prince “Thieves in the Temple”

83. Prince & the NPG “Diamonds and Pearls”

82. Madonna “Papa Don’t Preach”

81. Michael Jackson “They Don’t Care About Us”

80. Prince “Pink Cashmere”

79. Michael Jackson “Stranger in Moscow”

78. Madonna “Open Your Heart”

77. Michael Jackson “Who Is It”

76. Michael Jackson “I Wanna Be Where You Are”

75. Madonna “Material Girl”

74. Michael Jackson “Ben”

73. Madonna “Music”

72. Michael Jackson “She’s Out of My Life”

71. Madonna “Angel”

70. Michael Jackson “Will You Be There”

69. Madonna “Who’s That Girl”

68. Michael Jackson “Butterflies”

67. Madonna “Bedtime Story”

66. Prince & the NPG “Sexy MF”

65. Michael Jackson with Siedah Garrett “I Just Can’t Stop Loving You”

64. Prince and the Revolution “Let’s Go Crazy”

63. Madonna “Oh Father”

62. Madonna “Bad Girl”

61. Michael Jackson with Paul McCartney “Say Say Say”

60. Madonna “Get Together”

59. Madonna “Secret”

58. Michael Jackson “Love Never Felt So Good”

57. Prince “Soft and Wet”

56. Prince and the Revolution “Pop Life”

55. Michael Jackson “Dirty Diana”

54. Prince “Dirty Mind”

53. Madonna “Lucky Star”

52. Michael Jackson “Another Part of Me”

51. Michael Jackson “You Rock My World”

50. Prince “I Could Never Take the Place of Your Man”

49. Michael Jackson “Off the Wall”

48. Madonna “Like a Virgin”

47. Prince “Uptown”

46. Michael Jackson “In the Closet”

45. Madonna “Erotica”

44. Madonna “Keep It Together”

43. Madonna “True Blue”

42. Prince and the Revolution “Raspberry Beret”

41. Madonna “Dress You Up”

40. Michael Jackson “Don’t Stop ‘Til You Get Enough”

39. Prince “1999”

38. Madonna “Express Yourself”

37. Michael Jackson “Thriller”

36. Madonna “Crazy for You”

35. Prince “Sign o’ the Times”

34. Prince & the NPG “Gett Off”

33. Madonna “Everybody”

32. Prince “Do Me, Baby”

31. Madonna “Frozen”

30. Michael Jackson “Wanna Be Startin’ Something”

29. Prince “I Wanna Be Your Lover”

28. Madonna “Borderline”

27. Michael Jackson “P.Y.T. (Pretty Young Thing)“

26. Michael Jackson “Remember the Time”

25. Prince with Sheena Easton “U Got the Look”

24. Madonna “Deeper and Deeper”

23. Prince & the NPG “Insatiable”

22. Madonna “Live To Tell”

21. Madonna “Cherish”

20. Prince with Sheila E “A Love Bizarre”

19. Michael Jackson with Janet Jackson “Scream”

18. Prince and the Revolution “Kiss”

17. Michael Jackson “Human Nature”

16. Madonna “Like a Prayer”

15. Madonna “Into the Groove”

14. Prince “Alphabet St.”

13. Michael Jackson “Smooth Criminal”

12. Prince and the Revolution “Purple Rain”

11. Prince “Controversy”

10. Madonna “Justify My Love”

9. Prince and the Revolution “I Would Die 4 U”

8. Madonna “Hung Up”

7. Prince “Little Red Corvette”

6. Madonna “Vogue”

5. Michael Jackson “Billie Jean”

4. Madonna “Holiday”

3. Michael Jackson “Rock With You”

2. Prince “If I Was Your Girlfriend”

1. Prince and the Revolution “When Doves Cry”

*Note that because of Prince’s largely successful, fucking inane plan to “reclaim the internet,” none of his classic videos are on YouTube or any other reasonable streaming site. Instead, we have opted to post the covers of the Prince singles that ranked in the Top 21. The Prince material that is officially available on YouTube is his lackluster output from the past few years (and some random live shit), which gives an extremely skewed survey of his catalog to the modern, technology-savvy music listener. Prince is an asshole. Damn fine musician and pop star, though.

Update: Here’s a Spotify playlist of the ranked singles here as well as the songs I wish I could have ranked. Not everything on the list can be found on Spotify (especially not Prince’s independently released output), but most is there:

[Top images via AP]