Oh man.. This will just be too hard to answer.. For me anyway.. I like way too many.. But, mostly new ones.. I like the big 70's Caddy'e because they're BIG and have cool options.. Then, I like the big 80's years... And then the Northstars - all of 'em.. So many Cadillacs - so little time...
I never had an opinion one way or another for older ones. BUT - when the Northstar equipped Seville came to be - that was the first Caddy that I lusted after. So my favorite all-time would have to be the mid-90's Seville..
Let's see.........I like the......
'57 Eldorado Brougham
'59-64 Coupe DeVille (or any Coupe convertible)
'71-72 Eldorado Convertible
'75-76 Coupe DeVille
Of the ones I listed, I like the '75-76 Coupes the best......but I don't think I'd turn any nice two door Caddy away
My favorite would have to be first Cadillac, my first love, that has kept my heart to Cadillac since I was 8--the 1975 Cadillac Sedan Deville d'Elegance. It had so many electric buttons that I was fascinated and as I got older, I realized the extent of all of it's options. It was white with a white vinyl top. The interior was Manhattan (I love those names they used to give to everything), a dramatic two-tone crushed velour in dark blue. The car was loaded--Cruise Control, Tilt/Telescope steering wheel, Twilight Sentinel, Guidematic--Auto Dimming, Automatic Level Control, 8-track stereo tape player complete with the Cadillac Mancini Elegance 8-track, power passenger seat, electric rear window defogger, Theft Deterrent System, electric trunk release with power pull-down, Illuminated Entry System, Illuminated Vanity Mirror, Controlled Cycle Wipers, and remote passenger side mirror.
Standard features included Automatic Climate Control, power door locks, power windows, power antenna, power driver's seat and starter interlock system (you could not start the car unless all 3 front passengers had their seat belts fastened).
It was an amazing car that kept me with Cadillac all these years.
59 Coupe DeVille (I want mine back )
66-68 Coupe Deville (Hard top or convertable)
70 Coupe DeVille hard top
73-76 Eldo conv't
85 Fleetwood Coupe (minus the crappy 4.1 )
All my favorites. I need to get my aunts 49 Series 62 from her. She said I could have it after she passes away, but I don't want to wait that long. It's just sitting there collecting dust. It's been parked in the garage for the past 45 years. Interior is flawless and not an ounce of rust. One of these days