First Best Worst Last

First: Rock With You (could just as easily be Don't Stop Til You Get Enough... I don't remember) but I grew up knowing those.
Best: Human Nature, although it could be Thriller or a few of the others.
Worst: The Lady in My Life ... honestly I don't know if I dislike it, but on the Thriller album I usually would skip it.
Last: Thriller
 
This surprises me (to see anyone consider it his worst song). Not criticizing your choice AT ALL, just very shocked anyone would name this as worst. Very interesting, actually.
It's a top 5 song for me, especially with the guitar solo. But when we did the 70s unmadness, I noticed some of my top songs were on his worst list. So while we both love Chicago, we diverge elsewhere.
 
I guess I may have been a bit unfair to Michael Jackson as I am not as familiar with his overall body of work just his popular hits and of his popular hits I heard "Beat It" too much in college and did not care for it as much as others and never got over it. If I would have looked at it from that perspective with The Beatles, I would have picked "Help" as the worst popular song instead of Number 9. (a non-hit I think) Maybe I can still edit and change. But I do not hate the song. I even shook my eggbeater when we were playing it at a dorm party once, just as I do not hate "Help". Overall though, I would say I only like Michael Jackson while I love The Beatles. Not as much as I love Chicago but The Beatles would be high up there on my love list. I liked the recent Michael Jackson movie but did not go looking to play "Thriller" after seeing the movie though I did look at Jackson 5 stuff.

I did seem to forgive "Sussidio" (excuse spelling) for overplay in college so maybe someday I will think that way for "Beat It"
 
Overplay can certainly be a consideration. I see how you can feel that Beat It has been, umm, beaten to death. Probably some people factor that in, while others don't. Likewise, there may be songs you felt one way about when they came out, that you like more or less now. And you can decide whether to rank them based on old times, or today.

I love Squeeze. And I will include Tempted in the list of their best songs, because it's well made, and was very popular. But when I got the album East Side Story on record release day, I considered that song to be a throw-away ballad (before it got radio airplay). Then later, I kind of hated the song, because it was so overplayed, and (IMO) didn't represent the true style of the band, which was post-punk witty dance groove stuff. So I have a love-hate relationship with that song.
 
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