Cannonball Fever (1989) on Netflix

An assortment of greedy and eccentric people are forced to participate in the annual and illegal cross-country car race, the Cannonball Run. From Washington D.C. to Santa Monica, they race in order to claim a cash-prize money for the winner and runner ups. Oafish Charlie is forced to drive a BMW with bubble-brained starlet Tiffany. Alec is an English deadbeat who asks Mafia hit-man Vic, hired to kill him for outstanding bad loans, to travel with him in a Jaguar XJ-12. Alec hopes to use the prize money to get out of his debits. M.I.T. graduates and best friends Lea and Margaret participate in the race, driving a Ferrari Daytona Spyder, hoping to meet some good looking guys along the way. Valentino is a skittish Italian who teams up with Flash, an ex-cop, to drive a red Lamborghini Countach for business reasons. Heather and Jack are two TV reporters covering the action in their Ford Van and even partake in the race themselves. Nelson and Randolph Van Sloan are two wealthy and spoiled brothers driving a Bentley Corniche convertible and resort to dirty tricks to get ahead. Hounding the Cannonballers all along the way is the manic and corrupt police chief Spiro T. Edsel and his dim-witted aide, Whitman, hoping to stop the race and end the nuance the drivers cause by any means necessary.