Taking its nameplate from a coachbuilder historically associated with the General Motors division, the Cadillac Fleetwood became a stand-alone model line in 1985.

The first-generation Cadillac Fleetwood was introduced for 1985 as the division downsized its full-size C-body platform sedans to a front-wheel-drive layout.

The traditions of 300 years of coach-building that Fleetwood applied to its work on cars secured it a high reputation in automobile circles worldwide by the 1920s.

The Fleetwood script and crest would not be on the exterior of any Cadillac until the 1947 model year when it appeared on the rear deck lid of the Sixty Special.

The optional d'Elegance package, added tufted-button seating among other niceties for the FWD Fleetwood sedan.

Cadillac offered the Fleetwood Sixty Special for model years 1987–1988, using a stretched 115.8 inches (2,940 mm) version of the new C-body platform – as well as the Fleetwood Series 75 for model years 1985–1987, using a 134.4 inches (3,410 mm) stretched version of the same platform.

The Fleetwood line was redesigned for the 1989 model year to include skirted rear wheels.

The slightly revised Fleetwood coupe, with extended front and rear styling, was sold from 1989 and ended in 1992.

A total of 5,292 Sixty Specials were built during 1993, including 688 with the optional "Ultra" package that featured “22-way” adjustable front seats, designed in Italy by Giorgetto Giugiaro.

[14] Equipped with dual airbags as standard equipment, the 1993 Fleetwood marked the debut of the Cadillac "Airbank" SRS system, a wider passenger-side airbag designed to protect the right-side and center passenger riding in a front bench seat.

[14] On hiatus since 1986, the Fleetwood Brougham nameplate returned, as Cadillac restored it as the flagship option package for the model line.

Visibly distinguished by a full vinyl roof (which could be deleted), C-pillar and instrument panel badging, the Fleetwood Brougham also included model-specific seating designs for the six-way power seats (in either leather or Prestwick cloth) with three-position memory.

Alongside the Fleetwood Brougham option package, the Fleetwood offered multiple options, including a CD player, full-size spare tire, chrome wheels, sliding glass moonroof (dubbed "Astro Roof"), and an onboard security system.

[14] In contrast to the traditional usage of the D-body designation (prior to 1985), which was reserved for Cadillac limousines and its partially bodied commercial chassis (for hearses and ambulances), the post-downsizing D-body code is used for the version of the full-size B-body chassis specific to the Cadillac division; along with common powertrains, the Fleetwood shares a small degree of bodywork with the Chevrolet Caprice and Buick Roadmaster (visibly, the front doors and windshield).

For 1994, GM upgraded its full-size powertrains, with the D-body and B-body cars receiving a 260hp 5.7L LT1 V8, paired with an electronically-controlled 4L60E four-speed automatic.

Though more popular than Buick, Oldsmobile, and Chevrolet full-size station wagons, the Cadillac Fleetwood is the lowest-produced 1990s D/B-body sedan.

In its return to the D-body, the Fleetwood again supported the commercial chassis, an incomplete vehicle designed primarily for limousines and funeral coaches (hearses).

Following a long tradition of Lincoln-based sedans, this was only the second Cadillac since the 1983 Fleetwood built for the Ronald Reagan administration.

The production 2001 Cadillac de Ville (built for George W. Bush) was not regarded as suitable for conversion, so the final vehicle was constructed using the chassis and powertrain of a heavy-duty GM SUV, using little more than the front and rear bodywork of the de Ville.