Best was probably The Simpsons Sing The Blues CD the year it came out. It was something like the 3rd CD I owned 😅

The worst was probably this phone:

Nothing physical and not really merch, but I've recently played the free Lee Carvallos Putting Challenge and Lee Carvallos Putting Challenge 2 and both got me in tears.

I've got ~60 of The Simpsons Playmate figurines (I think some talk if you have the right play set.)

Back in college I was yard sailing looking for some junk to buy, not because I had money as a poor college student but because I could probably get some high quality crap for cheap.

Well we pulled up to a house and it just so happened they had a box full of Simpsons figurines. Some were new in-package, but most were just in good condition. The box said $1 each. Now mind you each of these figures was probably $5-$10 each, so that was a pretty good deal. I figured I could grab a few of my favorites for a couple of bucks.

As I was picking out my favorites I saw a man nearby looking at me. I quickly realized he was the current owner of these figures. He had the look of a man who, while ready to let them go, was sad to see his collection be picked apart.

We got to chatting for a bit when his (I assume) wife popped over and said "$50 for the lot". Both the man and I were surprised. That was a hell of a deal. I only had $50 to spend on crap, so my day of sailing from yard to yard would be over. But I also figured no one else would be reckless enough to buy them all. So I did.

Even as I brought them I'm not sure that man was really ready to let them go. But I do think letting them all go at once, to a fellow Simpsons fan, helped.

I've kept them in good condition over the years. I've opened the ones in-box since it just made the collection look nicer. I've never added to the collection, but it's still a nice collection.

I have a six pack of Buzz cola from when they made a 7-11 into a Kwik-E-Mart in 2007 to promote the movie.

Simpsons Chess. I swear it's from like 1990.

A giant Pez dispenser shaped like Homer's head. It dispenses entire packs of Pez and when you tilt his head back he says, "Mmmm..."

I'm not sure it's possible to catalog all of the merch since there's so much bootleg stuff out there (eat pant). I have a number of Simpsons tshirts, none of which are official. My favorite shirts are the one for the bus that couldn't slow down and the one featuring Mattingly and his sideburns. I think the least favorite things I owned were some of the NES and Game Boy games that I had, because most of the early Simpsons games were just awful.

I have a Homer clock that would say a Homer quote every hour. My grandpa got it for me at a garage sale so it meant a lot that he remembered something I liked. Since he said the same unique quote for every hour, I could tell what time it was based on the quote.

Unfortunately I had to put the clock in storage since it stopped working. The second hand kept getting stuck, even with new batteries.

I also have a pair of Homer slippers. I wore the hell out of them in college. I had to buy a new pair recently because of how worn out they were.

Late to reply here, but one item works for both: I have an unopened box of Homer Simpson’s Cinnamon Donut Cereal.

I had some Homer Simpson boxers I wore until it was more holes than shorts.

The only Simpsons thing I own anymore is a small, Bartman plush which is in storage. I used to have a 4 foot tall Homer I won at a faire, but he got a tear and all the stupid foam bead things started falling out making a mess so I had to toss him.

I've got the Bartman playmates figure and the early Bart plush with the plastic head and blue shirt.

I had one of those plushies when I was a kid, the Bart alarm clock, Bart Simpson's Guide to Life, the Bartman comic collection, the Simpsons Sing the Blues CD and the Do the Bartman single on cassette.

I remember having Bart Simpson hair gel when I was about 4 or 5 too.

I plan on buying all 6 Bartman comics and doing a 3D print of the Bart style Raven sitting on a bust of Pallis to put above my chamber door.