It all started with Buick celebrating its 50th anniversary. In 1953, the Buick Roadmaster Skylark was a two-door, specialty convertible. It was a limited production vehicle with the goal of promoting General Motors and its design capabilities. A first for Buick, it included a V8 engine as well as a 12-volt electrical system.

While it shared many features with the Roadmaster and Super models, most people don't realize that the seats in the vehicle were lowered to ensure that no one would hit their head when the top was up. Instead of completely changing the frame, the windshield was cut down a few inches and the side windows were also lowered.

Only a little over 1,600 were produced. While they began to sell well, sales declined and left many dealerships with the Skylarks left on the showroom floors. In order to sell the rest of the stock, most were sold at a discount. In 1954, the vehicle went through major style changes including changes in the interior and wheel well colors. A black Buick Skylark could be given either white or red wheel wells. Instead of all the hand stamping required in the previous year's model, the 54 was more of a production line vehicle. Unfortunately these changes contributed to the end of the Skylark line until 1961.

The Skylark returned as one of Buick's three new compact models, a two-door sedan with unique emblems and the option of a plush interior with bucket seats. The next year, the Skylark once again became its own model and no longer just a sub-series. It came in two different body styles including the two-door convertible and the two-door hardtop. A similar styling continued through to 1963 with the same two options for the Skylark.

One of the most notable changes of 1964 was the introduction of a third type of Skylark. The four-door sedan became available. These three options continued to be available until 1967, when five different body styles were offered. In the past, the Gran Sport had been a sub-series of the Skylark, but from the following year, Gran Sport went on to become its own line. Over the course of the next few years, the Buick Skylark continued to decline in its standing with the manufacturer as others came up to take its place. In 1972, once again the Skylark was discontinued and replaced by the new Buick Century.

Finally, in 1975, the Buick Skylark made a comeback. It consisted of the two-door sedan and hatchback sedan while the four-door stayed with the name of Apollo. There was both a higher and lower end Skylark produced at the same time. The Skylark S came with only the basic trim while the Skylark S/R was considered a more upscale version. In 1976, Skylark replaced Apollo as the name of the four-door sedan as well and in 1978, the upscale version of the vehicle was called the Skylark Custom instead of the S/R. However, it only lasted one year and was no longer produced.

The Skylark continued from 1980 to 1998 in a variety of different versions, sometimes as a stand-alone model and other times as a sub-series of another model.