2000s
Outkast - "Hey Ya!" - Good choice. They'll be playing this on the easy listening stations in ten years' time.
Kanye West (featuring Jamie Foxx) - "Gold Digger" - Again, good choice
Beyonce - "Single Ladies" - Trust me, high school reunions circa 2028 are going to bust this song out so damn hard.
Lady Gaga - "Bad Romance" - I would've gone with Poker Face, personally.
1990s
Nirvana - "Smells Like Teen Spirit" - Technically not pop. But whatever.
1980s
Michael Jackson - "Billie Jean" - This could have been basically anything on Thriller and it would have worked. It appears that each artist only gets one nomination, otherwise the 80s list would be all MJ all the time.
Prince - "Kiss" - Cream, Purple Rain, Strawberry Beret or Little Red Corvette are all better.
Madonna - "Borderline" - wat. Borderline over Material Girl, Like a Virgin, Like a Prayer and Spanish Lullaby?
1970s
James Brown - "Sex Machine" - Yes.
Stevie Wonder - "Superstition" - Yes.
Queen - "Boehemian Rhapsody" - Hell yes.
Bee Gees - "Stayin' Alive" - Got a ton of backlash in the early 80s, but it's still a triumph of human achievement.
Parliament/Funkadelic - "One Nation Under a Groove" - Yes. Very surprised to see a Parliament song nominated.
1960s
The Ronettes - "Be My Baby" - Yes
The Beatles - "I Wanna Hold Your Hand" - I'd have gone with Come Together, personally.
The Supremes - "Where Did Our Love Go?" - I prefer Baby Love
The Beach Boys - "God Only Knows" - I know better than to cross Beach Boys fanboys on this forum. I've learnt my lesson.
Marvin Gaye - "I Heard It Through the Grapevine" - Not Sexual Healing? WTF?
Jackson 5 - "I Want You Back" - Yes
Otis Redding - "I've Been Loving You Too Long (To Stop Now)" - I prefer Try a Little Tenderness
1950s
Johnny Cash - "Folsom Prison Blues" - Yep
Elvis Presley - "Jailhouse Rock" - Yep (though a few songs could work here)
Little Richard - "Tutti Frutti" - Filthy, filthy song.
Frank Sinatra - "I've Got You Under My Skin" - Yep
Buddy Holly - "That'll Be the Day" - Yep
Chuck Berry - "Johnny B. Goode" - Yep
Ray Charles - "What'd I Say" - Can't argue with this one.
1940s
The Andrews Sisters - "Boogie Woogie Bugle Boy"
Bing Crosby - "White Christmas"
Betty Hutton - "It Had to Be You" - Can't argue with any of these.
1930s
Duke Ellington - "It Dont Mean A Thing (If It Aint Got That Swing)"
Louis Armstrong - "Star Dust"
Fred Astaire - "Check to Cheek"
Judy Garland - "Over the Rainbow" - I had no clue these songs were this old.
Egregious omissions:
Eagles - Hotel California
Divinyls - I Touch Myself
Dusty Springfield - I Only Wanna Be With You
Usher - Caught Up
Maroon 5 - This Love