For me, it’s Ruth’s Chris Steak House. What is a ‘Chris Steak’? (I know she added her name to the original Chris Steak House, but that still doesn’t answer my question.)
Ruth’s Chris was the first thing to come to mind.
There’s a donut shop in town called Glory Hole that makes me cringe whenever someone mentions it.
Toys R Us always bugged the hell out of me. 'Cos for one thing, what exactly does that mean? All the toys are the same as a brick building that sells toys? This makes no sense! Also I was learning Russian as my foreign language in high school, so all the ‘use a backwards R as a real R’ situations (generally when someone wanted to make a thing ‘look Russian’, but also here), made me want to throw things.
“Ruth’s Chris” is not a thing here, but I endorse your complaint - it is a blackboard-scratchingly terrible name
Until recently, there was a womens’ clothing store chain called Dress Barn. It seemed to be a terrible name; who associates barns with nice clothing? (There was also a mattress store in the town where I grew up called Bedding Barn and that was also not a great name, but not as bad as Dress Barn.)
[Moderating]
This isn’t really about the arts. Moving to IMHO.
WaWa (gas station / convenience stores). I can scarcely say the name in a normal tone of voice.
They have awesome coffee though 
Well, there’s the chain of gas station convenience stores called Kum and Go.
For me it’s Piggly Wiggly. It sounds like pre-schoolish.
A dog grooming business around here is called Doggie Styles. Yuk, yuk, I get it, but it just seems to me you could have done better.
There’s a chain of organic grocery stores called Sprout’s Farmers Market. They’re not a farmers market, they’re a grocery store!
WaWa always struck me as baby talk. “Kum and Go”? That’s pretty bad!
Literally every time someone mentions an airline called “Virgin”, I think, what, like they’ve never done this before? Is that connotation the selling point?
I drove by a sign for a church in Memphis, Ram in the Bush. I almost had a wreck.
I believe there have been other threads complaining about this.
It’s not as stupid as the name of a product, called “iPod.” What a stupid name. It’s bad enough that they used it for their own product, but now it’s been genericized with the term “podcast.”
We’re stuck with that stupid word for eternity now–such a really good thing is degraded by such an asinine term.
Dick’s Sporting Goods
BJ’s Restaurant & Brewhouse
Both reasonably good businesses for what they are, but embarrassing to say.
I cannot bring myself to buy any of the foods make by “Boar’s Head.”
The name simply grosses me out.
Piggly Wiggly was the first ‘modern’ grocery store (in that the inventory was laid out on the shelves for borrowers to select, as opposed to old time stores where you gave your list to the grocer who went into the back to select your items for you).
When asked why he chose that name, founder Clarence Saunders is said to have remarked, “So people will ask that very question.”
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I don’t like Ruth’s Chris because it’s so damn hard to pronounce. It definitely doesn’t roll off the tongue.
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My contribution? I’ve been looking online for shorts - I found some great pairs from the Chubbies Shorts Company. Love their products; not so much a fan of the name.
Even worse, Facebook stalks me, and when I started searching online for good shorts I started seeing Facebook ads from a competitor - Bearbottom. Given the sexual connotation for the term ‘bear’ as a larger, hairy gay man, I just can’t.
I dislike Noodles & Company. It seems like it should just be… Noodle Company, I guess.
I’m not sure if I feel that so strongly just because Noodle Company really seems more correct or if St. Louis Bread Company (aka Panera, but nobody around here calls it that. It’s nearly always Breadco.) just drilled into me that that’s the proper format.
But you’re ok with the “bottom” part? 