While we have an Original Cadillac Ads photo album with many original 63 and 64 Cadillac Ads, I have picked up more over the years since creating that album and will be scanning the new ones and rescanning the old ones as needed.  As I scan and clean up the files I will post, and combine in a single album when I am done. For, some of these I have multiple copies and extras are for sale. i will start with 63's then move on to 64's and multiyear ads.

First up for 1963 is the "How Much Does a Cadillac Cost?" which features a 1963 Series 62 Sedan Four Window:

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Next for 1963 is "Cadillac Owners Don't Always Agree" which features a 1963 Series 75 Limo and a 1963 Series 62 convertible:

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Next for 1963 is "The Cadillac Car is a Vacation In Itself" which features a 1963 Series 62 Coupe in the foreground and a 1963 Four Window Sedan de Ville in the background.


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Next for 1963 is "Cadillac Owners Don't Always Agree" which features a 1963 Series 75 Limo and a 1963 Series 62 Convertible:

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Next for 1963 is "Cadillac Ladies Love to Play Chauffeur" which features a 1963 Series 62 Convertible.

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Gotta love the "Mad Men Era" advertising copy.  It definitely influenced me, as a young boy looking through my parents' latest copies of Life and National Geographic for the car ads.  Those were always in color, printed on larger format paper stock, and perfect for cutting out and taping to the walls of my bedroom.  (Bet I'm not alone in that.)

That was still an era when a man did man things, and a lovely woman would be waiting for him at home, wearing a beautiful dress with a martini in hand, and smelling of Chanel Number 5. 

I know now that was advertising fantasy. But, I truly believed that was what it was going to be like when I was an adult.  Once true adulthood arrived, it took me a while to get over that disappointment.  

But, my wife and I have played out that exact scenario a couple of times, just for fun. Pull up in the driveway in the Eldorado after a nice steak dinner, then put some Julie London on the hi-fi, mix a cocktail, and have a lovely evening...1964 style. 

Next for 1963 is "Sometimes When A Man Steps Away From His Cadillac" which features a 1963 Coupe de Ville.

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Next for 1963 is "Which Gentleman Just Joined the Cadillac Family?" which features a 1963 Coupe de Ville in the foreground and 1963 Four Window Sedan de Ville in the background.

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Next for 1963 is "When Chauffeurs Talk of Cadillacs?" which features a 1963 Coupe de Ville in the foreground and 1963 Fleetwood 60 Special in the background.

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Next for 1963 is "A New Cadillac And Its Closest Rival". Cadillac would often feature the current model year and a prior year in its ads. Here we see a 1963 Fleetwood 60 Special in the foreground, and a 1961 Series 62 Sedan Four Window in the background.

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Interesting to notice that in all these Cadillac ads you've posted, Jason, the "newest old car" is at least two years old. Never a one-year-old.

Maybe that's since Cadillac in those years did a remodel every two years, they would always be showing the last generation car in the ad, so as to not detract from sales of the current gen (in this case,1964) that looks similar to its previous year ('63.)

Thoughts?    

I think there were probably several reasons for using two year old prior Cadillac models including the reason you sited. Another take on this was posted by my friend Richard Sills who stated in part "It was brilliant marketing. It helped to support the market value of used Cadillacs. That, in turn, supported the proposition that buying a new Cadillac was a wise investment because of its retention of value."  Just fyi, you will see a lot more of this as we go to 1964 and beyond. 
Also keep in mind that in the 1960's many people tended to trade in cars every 2 or 3 years. That was also in line with the car's 2 year warranty. So a 1962 Cadillac Owner  from Fall 1962 to Summer 1963, when the 1963 model years were selling new, would have had a car still under warranty and relatively new. That would be like us trading in a 2023 we just bought last year for a 2024 this fall.  My best guess is the 2 to 3 year trade in average was the main reason for the 2 year gap.

Also note that the 1963 Fleetwood ad has a 1961 Series 62 in the background, which promotes moving up the body series line with the next Cadillac purchase. Just as GM had their own hierarchy between the makes, Cadillac had their own hierarchy between the entry level Series 62, to the mid-level de Villes, to the top of the line Fleetwoods and Eldorados.  Perhaps someone that is ready to trade in their 1961 might now consider an upgrade to a de Ville or even a Fleetwood 60 Special as featured.

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