Since bottomset thinks this forum is collapsing, it's time for another clickbait-type thread. Enjoy!
I'll get a few started off here. Feel free to contribute your own:
Into the Night - Benny Mardones (1980/1989)
This might be the creepiest song/video combination of all time. 34-year-old Mardones, who already kind of looks like a pedophile, sings about his obsession with a 16-year-old girl. The video shows the girl's father telling Mardones to "leave her alone", but instead Mardones proceeds to sneak into her room, take her away on a magic carpet, make out with her in the sky, and presumably do much more after the camera pans away.
Another strange thing about thing song was that it somehow got revived nine years later in 1989, simply because Los Angeles DJ Scott Shannon started playing the song in his "Where Are They Now?" segment, and that sent it back into the top 20 for another 17 weeks.
Lou Reed - Take a Walk on the Wild Side (1972)
This song had everything -- obvious lyrics about oral sex, male prostitution, and transsexuals. Even the chorus had a line which went, "And the colored girls go doot doot doot doot, doot doot doot", followed by colored girls doing exactly that.
It received mainstream airplay despite all of the above.
Mungo Jerry - In the Summertime (1970)
While the video featured probably the most obnoxious mutton chops seen on television, this song encourages both drunk driving ("have a drink, have a drive") and sexual assault of girls from poorer areas ("If her daddy's rich, take her out for a meal. If her daddy's poor, just do what you feel!")
The song was even protested at the time both by Mothers Against Drunk Driving and the National Organization for Women. But it still got plenty of airplay, and most people dismissed those lyrics as harmless.
Oingo Boingo - Little Girls (1981)
"I like little girls, they make me feel so good" and "Uh oh, I'm in trouble" would seem to be lyrics indicating support for pedophilia, but singer/songwriter Danny Elfman has made various excuses over the years that it isn't what it appears to be.
At one point, Elfman said it was satirical about older, sophisticated men who like surrounding themselves with very young trophy girlfriends. At another point, he claimed it was about his own girlfriend, who while a legal adult, was very physically small.
I believe that Elfman was just trying to be outrageous, which he did two other times in his "Only a Lad" album in 1981. Those songs included "Only a Lad" (mocking liberals being soft on crime committed by inner-city teenagers) and "Capitalism" (mocking spoiled college students protesting capitalism).
Fountains of Wayne - Stacy's Mom (2003)
The song was already questionable -- clearly about a teenage boy rejecting his girlfriend in favor of lusting after her single mom. However, the song itself seemed to be presenting a harmless fantasy of a teenage boy, and his advances are seemingly not returned by Stacys mom.
The video, however, is a different story. The boy featured looks about 14, as does his girlfriend "Stacy". However, the video clearly tries to sexualize Stacy herself, dressing her in skimpy outfits and engaging in seductive behavior, all of which the young teenage protagonist ignores because he's lusting after her mom. However, contrary to the song lyrics. Stacy's mom is shown clearly flirting with the boy, in various stages of undress, and at one point does a striptease for him.
The video ends with Stacy catching her 14-year-old boyfriend jerking off in the bathroom. Seriously.
With all the female teachers getting busted these days for sex with teenagers, there's no way this video would fly in 2018.
Neil Sedaka - Happy Birthday Sweet 16 (1961)
Sedaka was 22 himself when this was released, and he was supposed to be that age in the lyrics themselves. Neil sings about a girl finally turning 16, so he can finally date her, after watching her "grow up before my very eyes".
Creepy.
Check out this American Bandstand appearance, where Dick Clark inappropriately ogles the tights on a teenage girl in the audience, and asks her about them.
In Sedaka's defense, people got married young in those days, and it wasn't considered all that inappropriate for a 16-year-old to date men in their early 20s.