The original Chrysler 300, the 1955 model, began the famed run of "Letter Series" cars that ultimately ended in 1965 with the 300L. (The LH body 300M was supposedly a continuation of the Letter Series, and after having driven one for the last 7 years, I can say in many ways it was a worthy successor to the series.) The 1955 300 did not have a letter designation, but Chrysler put a "B" behind the 300 for 1956, indicating the second iteration of the marque. And after that the successive lettering continued until 1965 (with the omission of the letter "i" for obvious reasons).
Chrysler chose the name "300" in 1955 for their first attempt at a luxurious, sport-touring automobile because the dual 4 bbl, 331 cubic inch Hemi engine put out 300 horsepower, and was the first production American car ever to do so. But keep in mind the horsepower rating system in use at the time was SAE gross, not SAE net as it is today. SAE net horsepower for the original 300 was probably in the neighborhood of 230 to 240 bhp. So, even today's 3.5 300 models would qualify to wear the 300 badge under the old rating system, because they no doubt put out over 300 gross horsepower.
Horsepower of the original 300s steadily went up, with the most powerful 300 model ever produced being the 1960 300F Special, which was rated at 405 gross and came with a 4 speed manual transmission. A 60 300F Special was clocked at Daytona at over 170 mph, which given the car's weight of 4200 lbs, and not-so-great aerodynamics, would seem to indicate that maybe Chrysler was being a bit conservative with the published output.


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