Thought of another couple:

Winter of '79--Tom Robinson Band (old crusty revolutionary telling the kids they don't know how good they have it now, after the revolution)

Teach Your Children--Crosby, Stills, Nash & Young (addresses both generations, tells them they can't really understand the experiences of the other, but try anyway and know they love you--maybe a nice, hopeful note to end on)

Oh, and "Kid" by the Pretenders

The Fresh Prince entry is brilliance. Nails the OP request.

"Mothers of the Disappeared" is about Argentinian political opponents in the 1970's who were kidnapped and never seen again. "Killing in the Name Of" is about racist cops. "Summer of 69" is, more or less, about getting laid.

Well everyone takes something different away from different songs of course. Your opinion is yours to have. let me explain mine:
I always hear RATM as youth telling the establishment/adults to fuck off & get out of the way... and that song it very 'warfare'-y & the subtext to me has always been : "your old outdated KKK has no place in our world". I stand by the recommendation.

I included U2 MotD because it's about warfare and intergenerations... it's a stretch I guess, but perhaps the mothers aren't understanding why their kids are gone, and certainly Galtieri committed warfare against a younger generation through the kidnappings/murders.

Summer of 69 tells a story of a garage band kids growing up into adults with kids of their own.
"We were young and restless
We needed to unwind
I guess nothin' can last forever"
It's more an old man reminscing about his younger days: I'll take your crit on that one.

Oh dammit, HOW did I forget:

"A boy named Sue" - Johnny Cash

"girls just wanna have fun" - Cyndi lauper/Robert Hazard

arguably about resisting either parenthood or adulthood: "Responsibility" - mxpx

Likewise, "Papa don't preach" - Madonna

There's a great, long (80 pages??) profile of Haggard in a New Yorker from about 20 years ago. I think that's where I read that "Okie..." was originally written to be poke fun at the Muskogeeites, but people started taking it literally, and it rapidly became an anti-hippie, anti-marijuana, anti-hair, pro-flag, pro-Vietnam War anthem. The same article also contains a statement to the effect that, "Maybe we didn't smoke marijuana in Muskogee, but we smoked it everywhere else!" (approximate quote)

Um, "hope I die before I get old" is a lyric in "My Generation". "Teenage wasteland" is a lyric in "Baba O'Reilly". Neither are the names of songs.

Fnarf is correct, but I think both Who songs would fit nicely in this mix.