I drove a 5 series BMW for a while and my parents ignored my love for it and ended up buying a CTS. it didn’t even take them three years before they hated it enough to trade it in. Of course, they still wanted a caddy so they got an escalade and are well on they way to realizing they overpaid for the name again.
For generally driven a recognized cars I think Caddy is a tier 2 nice car. Of course the really rich people arent driving Beemers either its all maseratis and bentleys at that point.
Very long story - the GM products were individual lines until the Great Depression made them cheap.
See: History of General Motors
Cadillac, Lincoln and Chrysler were ultra expensive luxury marques - the 1932 Caddy cost 10x (yes, 10x) the cost of the 1932 Chevy.
See V-12 cars of 1930’s.
The tag “Body by Fischer” used by Caddilac for decades go back to the time when you bought the running gear (frame, engine, radiator - the complete car minus the body) and then shipped it to a snooty body fabricator (old buggy technology).
Fischer was a very snooty fabricator.
Caddy rode the image/heritage for 60 years.
The thugs “acquired” them for the same reason the rich had - status - you had “Made It” if you owned a Cadillac.
See GM “Ladder of Success”
Like some others have said, since about 1972 (to me anyways) not so much status.
That is when i noticed a distinct cheapening of the cars.
Before that though, i suppose you might say it was the american answer to the rolls royce.
I was never a caddy fan, though i do kind of like the 56 caddy
Or if you really needed MORE ROOM
At the time the caddy got you 500cid V8, automatic tranny, wide (for the time) 15" tires, power steering, power brakes, power windows, air conditioning, leather seats that were comfortable, plush carpets, enough room to house a small family, a ride that was smooth an isolated from the road, a cabin that was quiet, a heavy solid car body, a Radio and of course it was a Cadillac 
A lot of that stuff may sound kind of like eh so what today, but once upon a time it was not.
by 1976 it became pretty sad that massive 500 c.i. (8.2 liter) V8 only wheezed out 180 horsepower.
‘Cool status’ is basically 100% impression and if you get a reasonable sample of impressions, it answers the question. Unless it’s very skewed pro or anti- Caddy but most of the posts here are the conventional wisdom AFAIK.
Now, factually does Cadillac ‘think it has to go toe to toe with BMW on performance’, implying it doesn’t succeed? Doubtful AFAIK. I’m a BMW driver and fan, but I’ve read plenty of reviews putting the performance of performance-oriented Cadillac sedans of recent years equal to BMW’s if not in some cases superior. GM has put fairly serious money into achieving that.
Do you get a lot less for your money? Again doubtful AFAIK.
Is the build quality worse? Again I like my Beemer, quite a lot, but it’s detracted from a bit by an annoying door rattle/buzz now on rough pavement in an only 2-1/2 yr old car.
Reliability? Here there’s an objective semi-scientific source, Consumer Reports long term reliability charts. I don’t think CR has any axe to grind compiling them, though they do rely on owner reports, the source of ‘semi scientific’. In those BMW has an uneven record. My 2015 328i shows up well in those charts. Other BMW’s don’t. But few Caddy’s do really well. According to that source you’d look past either BMW or Cadillac if reliability across the brand was paramount, or again you’d significantly prefer some BMW models over others rather than generalizing too much.
I don’t like recent generation Cadillac exterior style. I like BMW’s much more. That doesn’t make either cool or not, you just naturally prefer a car you think looks better all else equal.
1972 really was the (too many old suckers dead) desperation point for Cadillac - they seized on the baby “car safety” laws (roll-overs killed many) to announce that the '72 Caddy would be the last converable GM (who cares?) would produce.
Many old suckers scraped up the pennies and "preserved’ (as best as Sears, Roebuck and Co could do), certain that, for the kids, the fast-rotting slab of crap would produce untold riches.
Check ebay for '72 Caddy.
It was about this time I heard that a Caddy cost GM $350 more to produce than a Chevy.
The Caddy was NEVER an “imitation” of anything (by the mid-80’s, they were desperate). They were the car that OTHERS tried to copy.
“Cheerios are the Cadillac of breakfast cereals” was a real thing.
the issue is that it’s clearly not sufficient, and it’s not even clear that it’s required at all. When you get into this class of vehicle, the brand/badge matter more than anything. Cadillac tarnished its brand years ago. And despite BMW’s old tag line of “The Ultimate Driving Machine,” I’d put money on it that most BMW buyers care more about the presence of that little blue & white round thing than any of its driving dynamics.
The “circles” that Escalade drivers is usually distasteful, even though we accept a Suburban in its lieu. I’ve got to say the same for our own offering (the Navigator); an Expedition is a high-end vehicle, but an Escalade/Navigator are just for gang-bangers or pretentious people. Just, yuck, despite their success.
That clarification really muddles the point for me. It started out as implying, to me, a claim that factually speaking Cadillac hasn’t matched BMW in performance, I’m assuming performance oriented sedans. I don’t think that’s true, but rather where GM has put the money into high performing Cadillac’s they are pretty much equal to BMW’s. At least a lot of car reviewers seem to have felt so.
And while that’s not a sufficient condition to win over any and all customers, which goes without saying, it’s a different question whether it’s a necessary condition or necessary enough to be worth doing. If it really was factually clear Cadillac was outclassed by BMW in performance, as was at one time arguable, where would that leave Cadillac? Just saying they ‘tarnished’ the brand is fine as permanent categorical put down from an outside POV. But if you’re GM management you’d want to figure out how to reverse that. Putting out performance cars which in fact stand comparison to BMW’s pretty well would seem to be part of that solution. Again it doesn’t change all the perceptions over night, or necessarily ever.
And for BMW itself it’s the same kind of dual issue. Yes perception of the brand is one factor onto itself at least short term. But if you put out products that in fact don’t support the perception, the perception eventually changes. Besides all the other possible pitfalls of brand perception (like the perception and fact being in tune, but just a perception that becomes less popular, a big part of Cadillac’s problem originally, not terrible cars, but cars of a style people of a certain generation appreciated but later generations less).
Otherwise though your statement seems to slide toward the (IMO) infamous last words ‘almost as good’. So the little ornament etc, compared to what? For getting from one place to another? OK lots of cars do that. Cheap cars in all ways as fun as mine, I don’t think so. And if I wanted to impress people I’d drive a Lambo, not a BMW 3. 
dudes, the El frikken Camino! thats like the Cadillac of Cars!
