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#1 ·
What are your 5 favorite years for Cadillacs? List them here and explain why, if you so desire.

My list:

#1. 1969. Nice front end and grille, elegant taillights, lots of chrome, last year for interior wood paneling (until it reappeared in the mid-'80s), great and powerful 472-cu-in engine, large and plush seats.

#2. 1970. Similar to 1969. Build quality, reliability, large and plush seats continue.

#3. 1968. Long, flowing lines, first year for the 472 engine, wood paneling on selected models, a temperature gauge, vent windows.

#4. 1966. The Fleetwood Brougham had rear picnic tables along with the footrests, 3/8" walnut trim, plenty of interior room, large seats, first year for the redesigned Fleetwood 75.

#5. A tie between 1959 and 1976...
1959. I love those fabulous fins! If one were parked in my garage, I could look at those fins for hours. A fine car to drive... smooth ride with a powerful and reliable engine. My choice: a '59 Eldorado Seville or a Limousine.

1976. Last of the pre-downsized Cadillacs. The DeVilles, Fleetwood Broughams and Fleetwood Seventy-Fives were as big as they would ever get. The 500-cu-in engines were refined and improved to the point where they would run better (especially when cold) than the '73-'74 engines due to all the emissions equipment.
 
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#2 ·
MOSTLY BASED ON EXTERIOR STYLING, IN NO PARTICULAR ORDER:

1) 1959/1960 - I prefer the over the top fins of '59, but '60 is a nicer overall design.
2) 1963/1964 - Much nicer than the '61/2 models.
3) 1957 - Much more elegant than the quad headlights of '58.
4) 1969/1970 - I lump them together because the only real difference is the taillights. I like them much more than the '65-'68.
5) '67/'68 Eldorado - Omitted the '69 because it lost the hideaway headlamps.

Mostly from the post war classic sweet spot between the 50s and '76. Of course, '39/'40 (and even the later 40s which introduced us to the eggcrate grille) was a good year and who can argue with the classics from the 30s. From later on, I really like the first and fourth gen Seville, '79 - 85 Eldorado, Allante roadster (I own one), and the last Fleetwoods. Lately, I really liked the '08+ CTS and recently discontinued XLR.

Getting the list down to 5 is pretty tough.
 
#3 ·
In order of preference:

1954: The first face lift after they received tailfins. I love the exaggerated, flowing lines that make them look so much bigger and prestigious. They're subtle, but still stand above other '50's cars and the entire package is punctuated by the gentle uprise of the tail-lamps.

1965: The first use of vertical, quad-headlamps. These cars offered more luxury than Ford or Chrysler, and stood out in the GM line-up while Lincoln and Chrysler just blended into their generic counterparts. I love the aggressive look of the front clip and the wide grill, which work to make the car look larger than life.

1974: This face lift makes the cars look the most dignified (they look marginally better in '75 and '76 with the square headlamps). This was the first year for the Fleetwood Talisman, which is perhaps the most coveted Cadillac model of all time. I love the size of these cars, combined with a return to subtlety in design. They aren't overdone, but everything about them says Cadillac

1948: The first year to have tailfins. The body looks very similar to the '47. It is as subtle as the '54, but a little simplistic.

1930: The first year for the Cadillac Sixteen. I like the style of '30's cars; back when coach built actually meant something.
 
#5 ·
In no particular order:

1977--First year for downsized Cadillac. Smaller, better handling cars that retain the roominess of their larger predecessors. Still have great power, reliability, and classic styling. Also, a well-designed interior.

1972--Strong, sculpted body lines, cleaner and less fussy than 1971 or 1973. Very classy looking cars across the whole line (and it's my birthyear! :) )

1969--Elegant front and rear treatment, excellent power and handling from a very large car.

1965--Cleaner design than 1966, with no center bar in the taillights or grille and a separate front license plate provision that gives the front bumper more presence.

1958--Totally over the top, chrome everywhere, esp. on the Sixty Special. Still more dignified than 1959.
 
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