American actor James Dean was killed at the age of 24 in an auto accident on September 30, 1955, near Cholame, California. He had previously competed in several auto racing events, and was traveling to a sports car racing competition when he was involved in a car crash at the junction of U.S. Route 466 (later SR 46) and SR 41.

In April 1954, after securing the co-starring role of Cal Trask in East of Eden, James Dean purchased a 1955 Triumph Tiger T110 650 cc motorcycle and, later, a used red 1953 MG TD sports car. In March 1955, Dean traded the MG for a new 1955 Porsche Speedster purchased from Competition Motors in Hollywood, California. He traded the Triumph T110 for a 1955 Triumph TR5 Trophy three days after filming wrapped on East of Eden. Just before filming began on Rebel Without a Cause, Dean competed in the Palm Springs Road Races with the Speedster on March 26–27. He finished first overall in Saturday's novice class, and second overall in the Sunday main event. Dean also raced the Speedster at Bakersfield on May 1–2, finishing first in class and third overall. His final race with the Speedster was at Santa Barbara on Memorial Day, May 30, where he started in the eighteenth position, working his way up to fourth before over-revving his engine and blowing a piston. He did not finish the race.

During the filming of Giant from June through mid-September, Warner Brothers had barred Dean from all racing activities. In July, Dean put down a deposit on a new Lotus Mark IX sports racer with Jay Chamberlain, a dealer in Burbank. Dean was told that the Lotus delivery would be delayed until autumn. On September 21, as Dean was finishing Giant, he suddenly traded in his Speedster at Competition Motors for a new, more powerful and faster 1955 Porsche 550 Spyder and entered the upcoming Salinas Road Race event scheduled for October 1–2. He also purchased a new 1955 Ford Country Squire station wagon to use for towing the "Little Bastard" to and from the races on an open wheel car trailer.

According to Lee Raskin, Porsche historian and author of James Dean: At Speed, Dean asked custom car painter and pinstriper Dean Jeffries to paint "Little Bastard" on the car:

Dean Jeffries, who had a paint shop next to [George] Barris, did the customizing work which consisted of: painting '130' in black non-permanent paint on the front hood, doors and rear deck lid. He also painted "Little Bastard" in script across the rear cowling. The red leather bucket seats and red tail stripes were original. The tail stripes were painted by the Stuttgart factory, which was customary on the Spyders for racing ID.

Purportedly, Dean had been given the nickname "Little Bastard" by Bill Hickman, a Warner Bros. stunt driver whom Dean befriended. Hickman was part of Dean's group driving to the Salinas Road Races on September 30, 1955. Hickman says he called Dean "little bastard", and Dean called Hickman "big bastard". Another version of the "Little Bastard" origin – corroborated by two of Dean's close friends, Phil Stern and Lew Bracker – is that Warner Bros. president Jack L. Warner had once referred to Dean as a little bastard after he refused to vacate his temporary East of Eden trailer on the studio's lot. And Dean wanted to get "even" with Warner by naming his race car "Little Bastard" and defiantly show that despite the racing ban during all filming, he would be racing the "Little Bastard" in between projects.

On September 30, 1955, Dean and his Porsche factory-trained mechanic, Rolf Wütherich, were at Competition Motors in Hollywood preparing the "Little Bastard" for the weekend sports car races at Salinas. Dean originally intended to tow the Porsche behind his 1955 Ford Country Squire station wagon, driven by Hickman and accompanied by professional photographer Sanford H. Roth, who was planning a photo story about Dean at the races for Collier's magazine. Because the Spyder had not yet been driven enough miles to qualify for the race, Wütherich recommended that Dean drive it to Salinas to accrue more time behind the wheel. The group had coffee and donuts at the Hollywood Ranch Market on Vine Street across from Competition Motors before leaving around 1:15 p.m. PST. They stopped for gas at a Mobil station on Ventura Boulevard at Beverly Glen Boulevard in Sherman Oaks at around 2:00 p.m. They then headed north on the Golden State Highway (US 99, later part of Interstate 5) and then through Grapevine toward Bakersfield.

At 3:30 p.m, Dean was stopped by California Highway Patrol (CHP) officer Otie V. Hunter at Mettler Station, south of Bakersfield, for driving 65 mph (105 km/h) in a 55 mph (89 km/h) zone. Hickman, following the Spyder in the Ford Country Squire with the trailer, was also ticketed for driving 20 mph (32 km/h) over the limit, as the speed limit for vehicles towing a trailer was 45 mph (72 km/h). After receiving the citations, Dean and Hickman headed west onto SR 166/SR 33 to avoid Bakersfield's slow 25 mph (40 km/h) downtown district. SR 166/SR 33 was a known shortcut for sports car drivers traveling to Salinas, called "the racer's road", which led to Blackwells Corner at US 466 (later SR 46). However, Dean biographer and expert Warren Beath disagrees with this account, citing Wütherich's inquest deposition stating that they had driven through Bakersfield and turned left on US 466. Beath, who lives in Bakersfield, emphasizes that SR 99 does not traverse downtown Bakersfield but instead skirts the city on the east side. In Hunter's testimony, he stated that Dean continued on to Bakersfield.