Milillo’s Pizza.
From Wikipedia:
Fifth Third Bank is a silly name.
Frickers is a chain of sports bars, mostly in Ohio.
Years ago, I had some professional contact with a now defunct local testing company called H. H. Holmes.
That name is closely associated with a serial killer in the late 19th century here in Chicago.
Testing company:
https://oakpointpartners.com/transaction/h-h-holmes-testing-laboratories-inc-remnant-assets/
Killer:
No, sir, I am not.
Beartop might work, if only I was gay myself. 
There’s a company that makes multimeters called Fluke. Terrible name. “If it works, it’s a fluke.”. Also, any company called Badcock.
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Cheesecake Factory. Who wants a cheesecake made on an assembly line? It also makes it sound like they have nothing but cheesecake.
Quiznos - a faux Italian name with no significance selected just to use two unusual letters.
Häagen-Dazs - likewise phony Danish.
I also agree with Ruth’s Chris Steakhouse.
I typically do the sad trombone sound when I drive past one.
Where many of the recipes came direct from that baaaad mother frickers (shut yo’ mouth!).
Not only Chicago. Thanks to the book The Devil in the White City, H. H. Holmes is infamous everywhere now.
My entry is always the Drury Inn. I see it as Dreary Inn.
There’s a chain of promotional goods here called Embroidme. Which drives me crazy as I think it really should have been EmbroiderMe.
Milillo’s sounds almost… mellifluous. Something in a dialect of Elvish. What would Elvish pizza taste like?
I agree wholeheartedly that the name Ruth’s Chris Steakhouse is the worst cacophony in business names. I’m inclined to agree with the dislike for the pseudo-Danish ice cream. If I were from Denmark I’d meet that with raised eyebrows and a flat “what” sufficient to express cold disdain with finality. I never registered Quizno’s as pseudo-Italian; it doesn’t track close enough with real Italian to sound like a match, it just sounds pseudo-businessese/commercialese as an excuse to use Q and Z at the same time, probably the inspiration for coining the original word quiz, however that may have come about.
Marie Callender’s? I get that it is actually the name of its founder, but I still picture a snooty boutique in a New England coastal town that only sells calendars. On an opposite note, when I lived in New Haven, CT there was a bar called C.O. Jones. Probably my favorite name for an establishment ever.
Yahoo and Google seemed pretty puerile to me, then the topper, GoDaddy. But then, grown-ups were not part of their business model.
I’ve never been crazy about the name of a furniture outlet around Texas called “The Dump”.
I feel the same way about “Off The Bone” lunchmeats. I eat meat and have no issue with eating meat off a bone, but there’s something about that name that I find very unappealing.
When I was in college, one of my male friends referred to Kum & Go as “Spurt & Split.”
There used to be an organization in my area called World Thrust Ministries. I see that the organization still exists (barely).
“Fuddruckers” always struck me as sounding like a euphemism for something you don’t want people doing in the same place where they cook your burger.
One wonders what they hang the donuts on.
There’s a long-running gay bar in Bangkok’s Patpong red-light district called Screw Boy.
There is a line of bluejeans in Thailand too call BJ. When I worked at the Bangkok Post, a lot of the Thai business editors got a free pair from the makers, and they thought they were great. They could not figure out why all of us Westerners there were cracking up.
Recently encountered this foolishness. “Look, I’m bad at math, and even I know that’s effed up. Why would I bank with someone who can’t even count on their fingers?”