Homerpalooza (S07, E24-152)

"I used to be with 'it', but then they changed what 'it' was.
Now, what I'm with isn't 'it', and what's 'it' seems weird and scary to me.
It'll happen to you."

Plot Summary
After Otto wrecks the school bus, Homer is tasked with carpooling some of the kids to school.  During these rides, Homer tries to make himself look cool to the other kids by listening to and talking about his favorite rock bands from the 70s, which drives the kids nuts.  Eventually, Bart has enough of it and tells Homer nobody cares about his 'dinosaur music'.  Distraught, Homer comes to realize that he's no longer cool.  Adamant on fixing that, Homer is able to snag three tickets for himself, Bart and Lisa to go to a 'Hullabalooza' in Capitol City, the cool concert at the time.

However, Homer's efforts start to go weary at the concert, as Homer still has no idea what's considered 'cool' nowadays (by which I mean the mid 90s), embarrassing his kids (again) and being mistaken as a narc by others.  Depressed, Homer kicks a machine, which then shoots a pig balloon right into his gut.  Homer is unharmed, which draws the intrigue of Hullabalooza's freak show organizer, who needs a guy to take cannonballs to the stomach.  In the effort to become cool again, Homer agrees, and goes on tour across the nation (except Ohio apparently).  As he gains admiration from his kids, and the tour going to Springfield on its next stop, Homer notices an oddity from his stomach.  The freak show director takes him to the vet, who informs Homer that all the cannonballs he's taken to the gut have essentially wrecked his stomach, and that if Homer takes just one more shot, he'll die.

Faced with the difficult decision of taking the shot to keep his cool streak going or not taking the shot to keep his living streak going, Homer takes the family to the Springfield Hullabalooza anyway.  When the big moment comes, Homer ducks away just in time, realizing that spending time with his family is more important than dying cool, although now his kids once more find him completely uncool.

Quick Review
Talk about dated.  I was never much a music guy, whether it was in the 90s or since, so maybe the guest starts aren't as great to me as the ones from, say, Homer at the Bat.  However, for a good chunk of the episode it really seems like its a battle between Homer's 70s-esque groove rock and the 90s counter culture which seems stupid by today's standards.

So, as such, there were a few jokes and references in there that I really didn't think was funny, and though a few of the guest spots like Cyprus Hill and Peter Frampton were funny, the other ones weren't doing much for laughs.  I guess you could say its one of those episodes that could only get worse with time.

Final Score: 7.2