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.

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.

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 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.

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.

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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.

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