The Wheeler Dealers (1963)

Based in Midland, Texas, Henry Tyroon, with a highly analytical mind, is a wealthy and knowledgeable proverbial wheeler dealer who over the past several years has focused on oil speculation. He likes to play up that good ol' boy Texas stereotype arguably to take advantage of potential business associates underestimating him, although three of those true elderly Texas good ol' boys, Ray J., Jay R., and J.R., will do whatever to buy into whatever Henry's latest venture in knowing his winning streak. When Henry's latest oil wells come up dry, he is forced to head to the financial center of New York City to raise $1.2 million in capital from possible investors, investments and other financial deals. Knowing that he can only raise part of that money from his regular investors, he heads to the brokerage firm of Bear, Osgood and Whitby to look into a partnership concerning tax shelters. Uninterested in such, partner Bullard Bear instead assigns his only female security analyst Molly Thatcher to be Henry's broker, she one of the few female analysts working on Wall Street and who Bear has also assigned to head one of their long held and forgotten securities, Universal Widget. In reality unknown to Molly, Bear and Whitby have assigned her this file in knowing that Universal Widget is a proverbial dog in it long not having manufactured anything let alone useless widgets despite the company still being incorporated in Massachusetts. They need to fire one analyst, and despite she more competent than most of her male counterparts, Bear wants an excuse to fire her as the token woman whose firing would minimize internal talk. Bear even hopes that Molly may be able to unload their investment in the company to unwitting Henry. But Henry being Henry, he finds a way to make money off the endeavor when he and Molly discover the reason why Universal Widget is still incorporated despite not actively doing anything besides existing. This move by Henry and by association Molly only complicates matters, especially as they slowly move their relationship from purely professional to personal, something Henry had wanted upon first setting eyes on her, the reason he went along with Bear's proposal despite knowing full well its general uselessness to him professionally.