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Luxury. Excess. Those tailfins. When you think of a classic Cadillac, the car that probably comes to mind first is the Eldorado, Caddy’s flagship coupe available between 1952-2002. Named to celebrate Cadillac’s golden anniversary, the Eldo started as a top-of-the-line convertible with luxe touches like power windows, a wraparound windshield and a station-seeking radio. It was also massive from the start, entering the market as an 18.4-foot-long behemoth. The 1959 Eldorado is the stuff of legend, thanks to its gigantic twin tail fins each with a double-bullet tail light (and its still-sprawling length). That kind of ostentatiousness couldn’t last; in 1960 the Eldo was immediately scaled back to a more modest version of luxury, and would continue refining its subtle charm through the next four decades. After a sportier Eldo emerged in 1967 akin to the Buick Riviera and Olds Toronado, the bigger-is-better crowd won out. Through the early ’70s, the Eldo would be the sole vehicle blessed (or burdened) with what was at the time the largest production engine on earth: a monster 500-cubic-inch V8. The Eldorado shrunk back to more normal size in the ’80s as fuel standards became more rigorous and ongoing engine issues plagued the car, and the even slimmer, boxier Eldorado shrank to compact-car size in 1986. A final redesign in 1992 brought the Eldo back closer to former glory, returning some performance and sportiness with alloy wheels, side cladding and the high-performance Northstar V8 engine as an option. It wasn’t enough to keep the Eldorado in production, though—GM decided fifty years was enough and the final Eldo rolled off the line in 2002.