Warren, speaking as someone who is near your age (just 3 years older) I think you're forgetting what it was like to be his age. I know this sucks - but sometimes kids HAVE to create their own identity that is separate from their parents. And listening to music that your parents is all about creating your own identity - especially if he is middle school aged.
He will likely look back in just a few years & realize the music he listened to sucked, just as I did when I was in high school (Ratt, Motley Crue, Twisted Sister). But nonetheless - none of that matters at his age. And even if you do consider yourself a relatively cool guy (at least compared to what you thought your dad was like), that still won't matter.
But - if you want to introduce to him some angst ridden ****ed up rock from our generation to prove that our generation had some cool music, try the following:
Butthole Surfers
Big Black
Throbbing Gristle
Sonic Youth
Unwound
Slint
He will either consider exploring his musical tastes, think that music over 10 years old is pure crap, or you might hate that music yourself.
But I'll find out myself - my daughter is only 7 months old so I will have a far greater gap to cover when she is old enough to listen to her own music.
By the way - did you play music you liked around him as he grew up? My wife shared a lot of music interest with her dad b/c he constantly played music he liked - Pink Floyd especially around her.
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