Pontiac benefitted from GM’s massive redesign for 1955, sharing much of its styling cues with contemporary Chevrolets and Buicks. The entry-level Chieftain had dog-leg windshields and was wider and lower, with straight-through fender lines and attractive two-tone paint jobs divided by bright trim. The hoods had wide stainless strips down each side and the massive front bumper was divided. The new look pushed Pontiac past 500,000 units for the first time, and placed the company sixth on the sales list for the year.

The Chieftain was sold in both Special and Deluxe lines, and carried Pontiac’s new 287-cid Strato-Streak OHV V-8 engine, which developed from 173 hp to 200 hp depending on carburetion. Four- and two-door Chieftain sedans were available, as were two-door Colony station wagons, two-door Catalina hardtops, and a four-door wagon.

For 1956, engines were bumped to 316 cid and power to as much as 227 hp. The Chieftain Special received two more models with two- and four-door Catalina hardtops, while the Custom line dropped the two-door sedan and gained a four-door Catalina hardtop sedan. The front bumper became a one-piece bar with round bumper guards and reverse slash body moldings appeared.

”Bunkie” Knudsen, who took the helm at Pontiac the previous year, asserted himself in 1957. For the Chieftain, the signature trim stripes on the hood were removed and a rocket-shaped side trim was added. Tailfins grew bigger and the hood was lower. More importantly, under new appointees Elliott “Pete” Estes and John DeLorean, Pontiac bumped its engine to 347 cid and tuning options on the Chieftain ranged from a four-barrel to Tri-Power. The base engine was now good for 252 hp, while the most powerful motor available on the Chieftain created 317 hp.

While the family similarity is obvious in all three years, and the paint schemes might be most attractive in 1955 models, Knudsen offered options in 1957 that practically doubled the horsepower from two years earlier (173 to 317). Knudsen himself entered a unique fuel-injected Chieftain at the 1957 Daytona Beach Speed week and set a lap record at 131.47 mph. Pontiac won the 160-mph Grand National Race on the beach course at 101.6 mph – 11 mph faster than the year before. For that reason, most collectors seek out a 1957 Pontiac Chieftain. The other years in this generation are also terrific examples of prime 1950s American automobiles, though not quite as fast.