Movies like Cadillac Man

For those captivated by Cadillac Man's portrayal of the high-stakes and morally ambiguous world of sales, Glengarry Glen Ross offers a darker, more intense look at real estate salesmen desperate to succeed, featuring powerful dialogue and memorable performances.

Cedar Rapids showcases the story of an insurance agent who encounters the wild side of a business convention, bringing a similar comedic touch to the professional world as seen in Cadillac Man, along with a heartwarming character journey that viewers are sure to enjoy.

Boiler Room dives into the high-pressure environment of stockbroking, analogous to the car salesmanship portrayed in Cadillac Man. It's a fast-paced, thrilling journey into the darker side of sales, which should enthrall viewers interested in the moral and ethical dilemmas of persuasive professions.

In Used Cars, the high-pressure and sometimes shady world of car salesmanship takes center stage. The film's combination of slapstick comedy and a touch of drama makes it an ideal companion piece for audiences who enjoyed the blend of humor and conflict in Cadillac Man.

The Big Kahuna, just like Cadillac Man, is a sharp and witty exploration of the world of salesmen. With a similar blend of humor and drama, it takes the audience into the intense and persuasive talks of corporate sales, which will appeal to those who enjoyed the fast-talking antics of Robin Williams' character in Cadillac Man.

The Goods: Live Hard, Sell Hard delivers a raunchier and over-the-top take on the world of used car salesmen, but maintains a similar comedic energy found in Cadillac Man, offering another humorous perspective on the lives of persuasive sales professionals.

Set in the cutthroat world of aluminum siding sales in the 1960s, Tin Men echos the competitive spirit and dark comedy found in Cadillac Man. Fans will appreciate the similar focus on the lives and schemes of salesmen, with a strong cast delivering equally compelling performances.