Briggs Cunningham met Phil Walters in 1949, with Walters racing under the pseudonym "Ted Tappet". Walters began driving for Cunningham, piloting a Cadillac-powered Healey Silverstone in 1950. Walters was also a partner in Frick-Tappet Motors, a company that converted Ford chassis by installing Cadillac V8 engines, creating vehicles known as "Fordillacs". Cunningham purchased a Fordillac after seeing one at a hill-climb, intending to enter it in the 1950 24 Hours of Le Mans, but the car was rejected due to the engine swap. Instead, Cunningham entered two Cadillac Series 61 cars.
One Cadillac, nicknamed "Petit Pataud" by the French, retained a largely stock appearance with modifications including a dual-carburetor intake manifold and brake cooling ducts. The second car, "Le Monstre", featured a custom aluminum body built over a metal tube framework, designed with the assistance of engineer Howard Weinmann from Grumman, and utilized five carburetors. Bob Blake was brought in to repair "Petit Pataud" after a pre-race incident with "Le Monstre", and later became responsible for building the cars until 1955. Cowles "Miles" Collier and Sam Collier drove "Petit Pataud" to tenth place, while Cunningham and Walters finished eleventh in "Le Monstre".
In preparation for the following year, Cunningham bought the Frick-Tappett Motors company, relocating it to West Palm Beach, Florida, and renaming it the "B. S. Cunningham Company". After fielding cars at Le Mans from 1951 to 1955, many team members retired following the 1955 Le Mans disaster. The company’s financial situation was also impacted by the IRS reclassifying it as a hobby in 1955, as it had not achieved profitability and racing expenses were no longer tax deductible. Briggs Cunningham subsequently wound up the operation and sold the factory.
The company produced several car models, beginning with the C-1 roadster in 1951, of which only one was built. The C-1 featured a 331 cu in (5,424 cc) Cadillac V8 engine and a custom-made De Dion tube rear suspension. It was tested at Le Mans but did not race, and finished fourth at the Mount Equinox hillclimb driven by John Fitch. This was followed by the C-2R, of which three were built for racing. Unable to secure Cadillac engines, Cunningham used a Chrysler FirePower V8 in the C-2R. The C-2R debuted at Le Mans in 1951, with the best result being eighteenth place for John Fitch and Phil Walters.
To homologate his cars for Le Mans, Cunningham undertook to build 25 examples of the C-3 road car. The C-3 used the 331 cu in (5,424 cc) Chrysler FirePower V8, producing 220 hp. Twenty-seven C3s were built, consisting of eighteen coupes and nine convertibles. The New York Museum of Modern Art named the C-3 Continental Coupé one of the "10 Best Contemporary Automobiles".
The C-4R and C-4RK were developed with the assistance of Bill Frick, and were lighter and shorter than the C-2R. The C-4R achieved several successes, including a fourth-place finish at the 1952 24 Hours of Le Mans, seventh and tenth-place finishes at the 1953 race, and a win at the 1953 12 Hours of Sebring. The C-4RK, a coupe designed in collaboration with Wunibald Kamm, finished tenth at Le Mans in 1953.
The C-5R, prepared for the 1953 24 Hours of Le Mans, was nicknamed "Le Requin Souriant" — the smiling shark — by the French. Driven by Phil Walters and John Fitch, it won its class and finished third overall. The final Cunningham racing car was the C-6R, which used an Offenhauser four-cylinder engine but retired at Le Mans in 1955.
An attempt to revive the company was made in 2001 by Bob Lutz and Briggs Cunningham III, with the unveiling of the C7 grand tourer at the Detroit Motor Show. However, the C7 remained a prototype and production did not commence. Cunningham cars are also credited with popularizing the racing stripe, initially representing the obscured blue frame rails on cars required to be white with blue rails for American international competition.