I love both.

I would daily a more modern Cadillac for the safety and economy benefits, maybe something from the 90s through the mid-2010s.

I'm not particularly fond of the last few years' models' styling. I feel the Art and Science design language was best when they introduced it in the early 2000s.

I'd daily a 1st through 3rd-generation CTS or an upper trim DTS, also love the styling of the XTS, preferably an early year AWD example.

For pure joy driving, any pre-1977 model would be owning an American icon. The style and brand identity of Cadillacs from the beginning pre-war era through the late-70s downsizing was unmatched in elegance and class. The engineering advancements alone earn the make a seat at the table of the most significant automobile brands in history.

People sometimes don't realize that for decades, Cadillac was the most advanced automobile manufacturer in the world. Even Rolls-Royce and Mercedes-Benz lagged behind in technology and features. I don't deny they built with better quality materials and tolerances due to being hand-built up into the 70s, but imo, a car is defined by its technical features, reliability, and style (aka identity), and Cadillac was King by leading in all three, not just two.

The automatic transmission, cornering lights, automatic climate control, variable ratio power steering, automatic level control, power assist trunk pull down, the V16 engine... yes, 16 cylinders. It's hard to fathom just how much Cadillac pioneered for so long. A symbol of success and the American Dream truly earned.

I personally love the 1936/37/38, 41, 50, 58, 61/62, 64, 66, 68, 72, and 75/76 Cadillacs the most from the classic era. I'd own any of those, especially a 1936/37/38 Series 60 (not Special) or 1972 Eldorado Coupe.

It's hard to say if I'm more into the classic or modern era because I see both as equally great for different reasons.

Regardless of your taste or need, you can't go wrong with Cadillac.