I had heard that it was about his disapproval of the circumstances of his pregnant sister’s wedding. With an ironic end note that his sister’s marriage was still going strong long after Idol’s own marriage had failed. But according to @Telemark 's article there was an incestuous element to the song, which is news to me.
‘I’m Proud to be an American’ by Lee Greenwood. Syrupy “freedumb” 'murka dregs. 'Nuff said.
A bunch of shit an old girlfriend used to subject me to. I gagged, she swooned:
- ‘Billy Don’t be a Hero’
- ‘Run Joey Run’
- ‘Having my Baby’
The actual song title is “God Bless the USA.” But agreed that it’s 100% cringeworthy. I had a client who used to open all their big meetings with it, and it was all I could do to not roll my eyes and make barfy faces.
Cat Stevens (as he was known at the time), Wild World.
“I’ll always remember you like a child” – why the hell do you think she’s leaving you? She’s sick of being treated as a child! (Either that, or worse, she was one – but now she’s grown up, and knows better than to stay.)
I forget that name of the song. . . a 90’s rock band. . . "Take my heart so tender, put it in a blender, spin it all around to a beautiful oblivion. . . " Gag! Man, that make me nauseous.
Thanks for the correction, and yeah, the difficult part is maintaining my decorum because I only hear that song in situations surrounded by freedumb fascists who near clutch their hearts as they try to croon along with it. My face muscles ache in trying to keep my scoffing, sneering and eye-rolling in check.
Oh, just thought about a rather modern cringeworthy song I still often hear on the radio that always gives me the creeps, “You And Me (In My Pocket)” by Millow. It’s a totally weird song about strange obsessions disguised as catchy pop song, with lines like:
I wish you were a little slower
Not just slow, but paralyzed
Then I could plug you into a socket
So you could never run away
I really wish that you were smaller
Not just small, but really, really short
So I could put you in my pocket
And carry you around all day
‘Inside Out’, by Eve 6. (Actually, I like that song.)
That would be Eve 6’s Inside Out, and I was going to mention it too, but I’m talking about the line
“…but the lack thereof would leave me empty inside”. Edgy. 
Booty Swing by Parov Stelar was released in 2012 and even used is some TV advertisements, yet contains lyrics like this:
Now, in the land of Fu Manchu,
The girls all now do the Suzie-Q,
Clap their hands in the center of the floor,
Saying, "Ching, ching, chop-suey, swing some more!
So I try
Oh my GAWD do I try
I don’t think most people realize that song is sarcastic passive aggression
I have trouble hearing it as sarcastic. Did the artist say it’s meant that way?
“If you wanna (Ugh) come before the deadline
Come in this jacuzzi, gerrymander in this coochie”
Billy Don’t Be a Hero’s lyrics are pretty deep IMHO. I mean sure the song’s not so great cause of the treacly presentation and worse…DRIVEN. Into. The. Ground.
You’ve got this idiot fooled by the jingoistic nonsense (Basically Starship Troopered) into going to war. His fiancee sees all the way through that nonsense. She’s pleading with him to just come back! But this dude seems to have a martyr complex. He dies…all she gets is a letter saying “She should be proud he died that way.”…and throws the letter away.
The rare piece of music that triggered in me the “turn that off what is this shyte” reaction and imprinted a lifetime loathing even before halfway into the very first instance I ever heard it.
“Starship Troopered”. Great observation. 
Yeah, hated the sugary presentation. More like a bowl of sugar lumps with honey poured over them. Plus the cheesy fife playing.
“I’d rather see you dead, little girl,
Than to be with another man.”
Wow, the Beatles seem to have quite a few of these.
Umm, “Johnny Get Angry”, Joanie Sommers. Good dog girl have some dignity. “Woman” Gary Puckett and the Union Gap (a woman has a certain look when she is on the move/and a man can always tell what’s on her mind/ I hate to have to say it, but that look’s all over you) Gah! It’s so disgusting. This song screams abuser.
Not exactly what the op meant, buuttt, Anything by Rush. I hate them so much I want to rip my ears off every time I hear their echo sound and the lead’s chalk board raking voice. Ugh.
The video specifically yes, definitely cringeworthy though arguably meant as a criticism of racism per the noted link and interview. Though the song itself is an allegory of American exceptionalism and economic imperialism without really anything to do with the video.