In the late 1970s I lived in a little house with a friend of mine on Pearl Street in Boulder Colorado. When they made Pearl into a pedestrian mall our rent went up so we moved out.
Later we saw that it had been converted into a store to sell quilts and sewing supplies. Still later, we were highly amused to see that it had been converted into a massage parlor of sorts. But in order to avoid laws about calling themselves a massage parlor if they didn’t have trained masseuses, instead they gave “feather rubs,” where they would stroke you gently with a feather duster. I kid you not.
The oddest one I can think of was when they converted an old Wetson’s (fast food hamburgers and the worst fries imaginable) into a sit-down Korean restaurant. You entered via the employees entrance to find a surprisingly nice looking dining room in the area where the burgers used to be cooked.
Another old fast food place around here, Red Barn, became a vacuum cleaner shop. It’s since been replaced by a used car dealership, and the red building painted beige.
Similarly, a Pizza Hut was converted to a different used car dealership.
Where I used to work, the new owner poured a lot of money into a new purpose-built facility across the parking lot from the original building, complete with tall windows facing the highway. We had the dock set up specifically for our operation and had a production waste handling system set in near the end of it. Then he sold the company, which later took all the equipment to a different location 30 miles away, to centralize and consolidate their operations in the region, selling the local property.
Now the new production building has been converted to an exercise franchise (only slightly altered, because it is a pretty structure in a bland neighborhood) and the original building across the parking lot is being used by some sort of construction contractor. I go through that area about once a month and see where I used to work with a different name on the building in lighted, 2’ tall letters.
Down the street from us was a nifty little Mom and Pop, stand-alone '50s (themed) diner. Every Friday and Saturday night, they would be packed with folks parking their restored jalopies, blaring Doo-Wop from their AC Delcos; it was a blast. Too bad the rest of the week was a wasteland–they moved 10 miles up the road to a busier town, but it ain’t the same. Now, it’s a video poker joint; there are 5 more within 500 yards, right next to the three bail bond outfits. Think there’s a connection?
A friend and her husband took the big leap into entrepreneurship and converted a former furniture store into an “action park.” Go-kart racing, multi-level laser tag, climbing wall, etc. It’s still new, so no idea how it will work out.
Right down the street from me, a jewelry store moved into a space vacated by a dry cleaner. The cleaner had a drive-through window, and now we have a jeweler with an “express jewelry repair drop off.”
No especially odd business transitions come to mind, but how about a government one? My primary school was before that a high school, then an elementary school*. The last year that I was there was the last year it was a school and afterwards it became the town hall. This is all in the same physical structure–before that, different buildings on the same site was a hotel (that was the largest building in the state at the time) which burned and was replaced by a women’s college which became a hotel again which became an elementary school.**
*The distinction between them being “elementary” was grades 1-8 and “primary” grades 1-4.
**To demuddle that a little, in the course of three physical structures built in succession on the same site: building 1: hotel (burned) building 2: college to hotel to elementary school (replaced) building 3: high school to elementary school to primary school to town hall.
Kitchener, Ontario was famous for having a 75,000 sq ft K-Mart store turned into a night club/rock music venue called Lulu’s Roadhouse, complete with what was once the world’s longest bar. I went there a couple of times to see James Brown and Doug & the Slugs. The long rectangular shape of the club always seemed a little odd to me, though.
One of the stranger transformations was the Southwest City Mall. IIRC it had a Woolco, Osco Drug, DMV, OTASCO, Safeway, many small shops, and a wonderful cafeteria. I was there every week shopping and dining at the cafeteria. I met my real estate agent there for lunch and signed the offer to buy my house.
They had an arts and crafts festival in the mall in Nov. Bought many items for Christmas Gifts.
Woolco closed first. A new dept store opened in that space. I think it was a Sterling Store/Magic Mart.
Gradually all the stores I listed closed. Usually because the entire Store Chain closed.
Osco Drug, Safeway, and the cafeteria survived until 94 or 95.
That old mall is now the headquarters for The Arkansas State Police. Still looks the same on the outside. No businesses there any more. The DMV is still there.
So many memories and good times. It’s strange that it’s gone.
There used to be a most striking-looking office building in an area that was mostly retail. It had a triangular inward-sloping window wall that converged to the main entrance at the bottom. To a teenage male, the lines were quite evocative – we called it “muff plaza”. It was razed a few decades ago and now there is a tony furniture store and some other retail in that general area.
Same was done in Greenville, SC. McAlister Square now holds classrooms for a community college and satellite campus for some other area universities.
In Cayman the old two screen cinema could not keep up when a new six screen theater opened. The old site was repurposed as an office supply store. Not sure what they did but there is no sloping floor to negotiate.
We had a Safeway that became a disco for a couple of years.
I know a Wendy’s that is now a dentist’s office.
Not quite what the OP is looking for but I want to share it anyway. Back in the day Taco Bell restaurants were stand alone buildings with a distinctive Mission style to the exterior. Arched windows, curved roof tiles and a little belfry on top. in our area, they all closed around 1980 or so. I heard there was some kind of non-compete agreement with another local chain, so we had no Taco Bells for fifteen or twenty years.
About ten years after they closed my sister and her boyfriend bought one of the old buildings, which had stood empty the whole time, and turned it into a fish and chips place.
On opening day, a fellow came in and said to my sister, “My grandma got a burrito here last night and it didn’t taste right.”
Highly amused, my sister pointed up at the menu and said, “Which burrito was it?” The scammer looked and, seeing nothing but seafood-related items, became flustered and quietly slunk away.