This isn't a Goodwill find but it sort of counts since I'm using it with items I got from Goodwill over the years. For a long time now I've wanted to pick up a Bluetooth Cassette adapter. I know they've been around for quite awhile now (2014 according to the DuckDuckGo AI Search Assist) and they've always been fairly cheap but for some reason it took me until 2025 to finally get one.
This is the one I decided to go with
Arsvita Car Audio Bluetooth Wireless Cassette Receiver
I think it is just awesome!

I just find it pretty neat that you can turn a 30+ year old cassette player into a modern bluetooth speaker that you can easily connect to your phone or computer. Even if the cassette deck has a broken belt or even a non functioning motor it will still work just fine with the BT adapter. All it needs is for the playback head of the cassette deck to come in contact with the head on the BT adapter.
So I've been having fun connecting it to various random cassette decks I've got laying around. A few which have never worked since I've owned them. Who knows when the last time some of these have actually had audio playing through them. Here are some of the cassette players I've tried it out with. And no this isn't even close to all the cassette players I own. I have a ton more boomboxes, and yes I know I own WAYYYY too much old stuff like this and really need to get rid of a lot of it. At least I'm not buying more of it anymore, partially because I'm not as interested in it all as I once was and also because Goodwill hardly has anything decent anymore and the rare times they do for the most part the stuff is way overpriced.
Comes in a big leather case with a lid, bought it several years back because it was cheap and looked kind of neat. Check out that awesome 80s computer font on the bottom right that says "Sync/Dissolve System"
A Sankyo deck I got many years ago at a flea market that was in a bundle with some other stuff. It has never worked so this is the first time in probably 20 years or more it has had audio playing through it! I've never heard of Sankyo before. Sounds like what someone might say when asked what happened to the Titanic. It Sankyo.
A GE cassette player/recorder that looks to be from the very early 80s. Believe it or not it actually still plays tapes although the speed is a bit slow. Still it is pretty impressive that it can still play tapes with the original 40+ year old belt.
Just your standard tape player of the time. I've got a few that are similar to this design. This is the kind you might have seen hooked to a computer back in the 80s for cassette storage.
My first Ghettoblaster!

I was really hoping this worked when I bought it many years ago. The radio works fine but the cassette deck has seen better days. I think it just needs a belt replacement but it sounds pretty rough when you try to play it. At least I was finally able to play some audio through the cassette with the BT adapter.
This one sounds pretty decent and I'm actually using it as a speaker for my PC sometimes with the BT adapter. It sounds better than the built-in speakers of my flat screen TV and when I'm watching Youtube in bed late at night I can move it close to my bed so I can hear it better without having to crank the volume up.
This one is just plain cool looking. I've always preferred silver electronics over black ones. Funny how many silver electronics from the 70s look more modern than lots of the black ones from the 90s, well they do imo anyways. It has a setting for Stereo and Ambience. I would describe the Ambience setting an as early simulated surround sound setting. I did a quick search about it to see what it actually does and it seems I was pretty much right.
"The ambience setting on a boombox enhances the stereo sound by creating a wider soundstage, making it feel like the audio is coming from multiple directions rather than just the speakers. This effect is achieved through circuitry that introduces slight delays between the left and right audio signals."
Another awesome looking silver Panasonic with Ambience. They both are really nice looking but I think I like this one the best out of the two.
A unique Realistic from 1986-1988 with "Stereo Wide 4" which is just two additional speakers on the top. This one also actually works fine with playing real cassette tapes. Again I find that pretty impressive considering the belt is 37-39 years old! I found an old Radioshack ad for it while looking it up online and it was $99.95 back around 86-88. Doesn't seem like that bad of a price until you realize that is around $270-$295 with inflation. There are only two of these available on Ebay, both seller are asking $59.99 and neither of them work properly. Maybe I have the only full functional one left!
8-track to cassette adapter