Olives were way too meaty.

Do you know what kind of olives you used? There's such a great range in sizes and flavors, from big, plump, and mild Cerignolas, to sharp and salty Kalamatas. In addition to the variations in the type of olive, there are many ways to cure them, each infusing a different kind of flavor profile, such as lemon, garlic, and rosemary, and a great range in saltiness. If you have a deli nearby that has bulk olives, you might see if you could sample several varieties and see if there is one that would fit what you are looking for.

The jack cheese would 'smooth out' the so called meatiness of the olives..making a nice mouth feel with melted cheese interior, in cased in the olive shell.
Make a test run with it with some of the picky eaters and see what they think.

Tho, I'd bet they'd probably like MORE CHEESE LESS OLIVE. In that case, chop up the olives and add them to shredded jack and compress into balls and bread and fry.

what would that do?

"I was thinking about hollowing them out a bit.. More work yeah, but if I can reduce the meatiness a tad.. then perhaps I can win over the critics."

Try stuffing them with some jack cheese..and then frying.

The fry fest was awesome. 4 people frying up all kinds of good stuff.. Including pickles. :) And a bunch of other stuff. Even fried up some white castle burgers.. Which was awesome.. But about the olives... I was thinking about hollowing them out a bit.. More work yeah, but if I can reduce the meatiness a tad.. then perhaps I can win over the critics.

oh..second thought. If you do the firecracker shrimp. Ditch the thai sweet chili sauce and sub some normal bottled BBQ sauce. After seeing you're in a small town, you really don't want to challenge your audience too much with unfamiliar flavors. That said, I sometimes fine the thai sweet chili sauce a bit too overwhelming/sweet on that shrimp. (most likely because I can't find really good thai sweet chili sauce here)

Another suggestion. Make some Fried Dilled Pickle Chips for the next fry fest.
Easily recognizable to the masses as 'fried dilled pickle chips'...so no unexpected challenges on expectations there.
Serve with a remoulade...or a siriacha/mayo dipping sauce.

Okay, off topic a bit---but still about a 'fry fest'.
SteamyKitchen's "firecracker shrimp" isn't just good, it's excellent.
http://steamykitchen.com/72-crispy-shrimp-springroll-with-sweet-chili-sauce.html

Small town in the Midwest here.. So, options are very limited...

Graber Olives are a nice mild variety, but large and meaty, but they may only be local to SoCal. Kalamata's can be meaty and bitter to some. I dislike 'supermarket' black olives.

I'll look into what i have available locally. Thanks hardlikearmour..

Maybe go with a milder green olive like castelvetrano.

Thanks Sam..

It's a matter of taste. I'd say quite a few people have never tasted a really good olives, so it's a bit strange to them.

They're used to the mass market canned, take out pizza, taco joint, type cocktail olives that have most of the flavor sucked out of them, leaving them inoffensive little slightly olive flavored cardboard spheres--which regrettably most of America accept (and expect) as "olives".

The only suggestion I could make is make both groups happy with "cocktail olives" for some and artisan olives for olive lovers.