Cadillac had a budding problem as the 1990s drew to a close: Crosstown Detroit rival Lincoln had a smash hit on its hands with the then-new Navigator, SUVs were taking off in general, and it had nothing to offer its dealers. General Motors had a new GMT820 truck platform in the works, but it wouldn’t be ready to underpin the Chevrolet Tahoe and GMC Yukon—and, as planned, a new tall Cadillac—until 2000. Facing down two years of missed sales and brand reinforcement, Cadillac visited the GMC dealer.

1999 Cadillac Escalade

We’re not being goofy here. Cadillac, in a pinch, simply borrowed GMC’s range-topping Yukon Denali and slapped its own badges and wheel caps on it. (The GMC-specific seat embroidery, too, was changed in favor of Cadillac logos, and the exterior cladding on the lower doors was said to be unique to the Escalade.) Thus was born the first-ever Escalade, which was sold for two model years between 1999 and 2000. It was a stopgap measure intended to float Cadillac along in the luxury SUV space until the more original GMT820-based design arrived for the 2002 model year in 2001. And it worked. About 50,000 Escalades were sold during the model’s brief first generation.

1999 GMC Yukon Denali1999 GMC Yukon Denali
This is the ’99 GMC Yukon Denali—can’t you tell?

Funnily enough, not many people remember the first-generation Escalade. This has more to do, probably, with the iconic status the second-generation model achieved than with the original’s somewhat anonymous appearance. The 2002–2006 Escalade, resplendent in Cadillac’s angular Art & Science design language and sharing only its basic body shape with lesser GM SUVs, became a pop-culture staple and was an MTV regular.

The 1999–2000 Escalade came with a 255-horsepower 5.7-liter V-8 engine, a four-speed automatic transmission, Bilstein shocks, and an AutoTrac all-wheel-drive system. It was a nicely equipped rig, too, with a better warranty than its GM stablemates and standard OnStar, leather seats (power-adjustable in front), heated exterior mirrors, Bose sound system, and separate rear-seat climate controls. It was essentially mono-spec, with no major options available. Keep that in mind should you feel like trolling Craigslist for a used one—because boy, are these things cheap nowadays. Credit, again, the original Escalade’s relative obscurity for decent examples with high-ish miles seemingly going for under $5,000 all day.

We find it historically amusing that Cadillac, which for most of the ’90s was on a roll differentiating its products from those of lesser General Motors brands, decided to badge-engineer what would later become its best-known model into existence. Anyone who remembers the 1980s remembers the low points for GM’s cross-pollination of models across brands, which peaked (bottomed?) with the Chevy Cavalier–based Cadillac Cimarron compact sedan. But the Escalade persevered; rising above its shortcut, microwave-dinner roots to become an icon. And now it’s entering its fourth generation for 2021, as differentiated from its recently redesigned Chevy and GMC siblings as ever before.

1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade

1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade
1999 Cadillac Escalade

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