1956 Pontiac Star Chief Convertible

Pontiac’s Star Chief was a full-size offering available between 1947 and 1966, across six generations. It represented the top trim level for the Chieftain model, and as such, sat at the upper echelons of Pontiac’s hierarchy. Today’s 1957 Pontiac Star Chief Custom Safary 2-Door Wagon Restomod is a bit different, though. It’s a restomod with some neat upgrades and makes for a fine classic daily driver. With over 120,000 miles on the clock, this car has been around quite a bit, but it’s not tired at all. Rather, this Riverside-based Pontiac is ready for even more action if you please. It’s got a 347ci V8 with FiTech Go Tri-Power electronic fuel injection, an aftermarket audio system and even air conditioning!

Pontiac, one of those great American brands that is no more, is something of a legend. Between 1926 and 2010, they’ve given us plenty of great nameplates, some truly awesome muscle cars, potent pony cars and flamboyant full-size sedans. One of their key offerings in that last segment between 1954 and 1966 was the Star Chief. This was initially a top trim package for the Chieftain model before becoming a separate model. Finding a Star Chief isn’t easy because these vehicles were never intended to be collectibles. That’s despite over 203,000 being made in 1955, the year from which this 1955 Pontiac Star Chief hails. So if you wish to own this vehicle, you’d better act fast as it’s in great condition. It’s currently domiciled in Lake Elsinore, California, if you’re interested to go check it out.

With a name like Star Chief, this Pontiac immediately exudes a very native vibe. Initially used to represent the top tier trim of the equally interesting Chieftain line-up, the Star Chief was spun off into a separate model very soon. Today, we have a 1956 Pontiac Star Chief Custom Safari 2-Door Wagon which is a two-door wagon body style that was introduced to the line-up in 1955. This particular example hails from Madera, California, and has done 57,000 miles so far. Plus, it’s got a host of upgrades and enhancements for you to enjoy.

The 1999 Pontiac Firebird Trans Am WS6 is one of the most recognizable performance cars of the fourth-generation F-body era, combining aggressive styling with LS1 V8 power and the added hardware of Pontiac’s WS6 Performance Package. This example shows approximately 28,881 miles and is finished in Bright Red over a Taupe interior. It also features removable T-top roof panels, 17-inch aluminum wheels, a limited-slip differential, dual exhaust, and the signature rear spoiler. With low mileage for its age and the sought-after WS6 package, this Trans Am captures the raw, unmistakably American performance character that made these cars so memorable.

The 1959 Pontiac Catalina Convertible captures Pontiac at the dawn of its Wide-Track era, when the division was moving toward the bold styling and performance identity that would define the 1960s. Showing just 3,138 miles, this Catalina combines its sweeping open-top bodywork with a 389ci V8, 2-barrel carburetor, and 4-speed Super Hydra-Matic automatic transmission. Power steering, power brakes, factory air conditioning, and a power-operated convertible top add desirable cruising amenities to a car already defined by unmistakable late-1950s presence.

This 1992 Pontiac Firebird Formula takes the familiar third-generation F-body formula and adds a substantial list of performance-oriented upgrades beneath the surface. Showing approximately 178,966 miles, the current owner reports approximately 1,000 miles on the current engine build. Power comes from a 5.7L naturally aspirated small-block V8 paired with a 5-speed automatic transmission and rear-wheel drive. The build is highlighted by Holley Sniper electronic fuel injection, an aftermarket intake manifold and exhaust headers, upgraded fuel delivery, and a Mishimoto cooling system. Removable T-top roof panels add another layer of classic Firebird appeal, making this an enthusiast-focused example with unmistakable early-'90s styling and a substantially reworked V8 powertrain.

The Mercedes-Benz SL has enjoyed a distinguished place in automotive history, and the R107 generation remains one of the most celebrated luxury roadsters to emerge from Stuttgart. Produced from 1971 through 1989, the R107 became synonymous with sophisticated open-top motoring, exceptional engineering, and the understated elegance that defined Mercedes-Benz during the era. Introduced for the 1986 model year, the 560 SL became the flagship American-market version of the R107, bringing a larger 5.6-liter V8 and further refinements to an already accomplished grand tourer. This 1987 Mercedes-Benz 560 SL, showing 65,981 miles, is finished in Arctic White over a Palomino leather interior, complemented by a contrasting Dark Brown convertible soft top. Its factory specification is particularly appealing, featuring a rear spoiler delete that preserves the roadster's clean, classic proportions. Additional highlights include a removable body-color hardtop, 15-inch Mercedes-Benz alloy wheels, automatic climate control, heated exterior mirrors, and a Pioneer audio head unit replacing the original Becker radio. With its elegant color combination, naturally aspirated V8, and timeless R107 styling, this 560 SL offers an inviting opportunity to experience one of Mercedes-Benz's most enduring grand touring roadsters.

The Lincoln Mark VII LSC brought an unexpected dose of performance to the American luxury coupe market during the 1980s, combining the comfort and refinement expected of Lincoln with the same 5.0-liter High Output V8 that powered Ford's celebrated Mustang GT. By 1990, the Mark VII had established itself as a distinctive alternative to European grand touring coupes, offering rear-wheel drive, four-wheel air suspension, and a remarkably well-appointed interior. This 1990 Lincoln Mark VII LSC Special Edition, showing just 47,063 miles, is finished in Garnet Red over Titanium Gray leather and belongs to a particularly limited production group. Reportedly only 3,345 LSC Special Edition examples were produced for 1990, with just 442 sharing this particular paint and trim combination. Its Special Edition appointments, monochromatic exterior styling, distinctive lace-style aluminum wheels, and powerful 5.0-liter V8 make it an appealing example of Lincoln's performance-oriented luxury flagship. With its distinctive specification, low indicated mileage, and documented production figures reported by the seller, this Mark VII deserves attention from collectors and enthusiasts of American luxury automobiles.

The 1966 Cadillac Coupe DeVille captures the grandeur of American luxury motoring during the 1960s, when Cadillac's expansive proportions, distinctive styling, and powerful V8 engines made the marque a benchmark for premium automobiles. For 1966, the Coupe DeVille featured refined exterior styling, a broad front grille, and an elegant two-door hardtop silhouette that emphasized Cadillac's reputation for comfort and sophistication. This particular example, showing 87,314 miles, is finished in distinctive Mint Green with a matching Green interior, creating a classic period-inspired color combination. Beneath the hood sits a 429ci V8 paired with a 3-speed automatic transmission, delivering the effortless power expected of Cadillac's flagship luxury coupes. What sets this example apart is its Air Lift Performance air suspension system, featuring dual VIAIR compressors and a custom air tank setup, allowing for adjustable ride height while maintaining its traditional appearance. With its classic Cadillac wheel covers, whitewall tires, and upgraded suspension, this Coupe DeVille offers a distinctive combination of vintage American luxury and custom cruising character.