"Of Late I Think of Cliffordville" is the 116th episode of The Twilight Zone.
From the CBS Video Library cover:
"Elderly millionaire William J. Feathersmith is bored with his life. At the top of the financial ladder, he finds no more challenges to excite him. When the satanic Miss Devlin offers him a return to the hometown of his youth in order to again experience the thrill of clawing his way to the top, Feathersmith readily agrees. The price for the deal is his entire fortune, all but $1400 (they already have his soul).
Feathersmith soon finds himself in the Cliffordville of his youth. Both he and the town look exactly as they did in 1910. But Feathersmith will find that the town is not as he remembered it...and neither is he."
"Witness a murder. The killer is Mr. William Feathersmith, a robber baron whose body composition is made up of a refrigeration plant covered by thick skin. In a moment, Mr. Feathersmith will proceed on his daily course of conquest and calumny with yet another business dealing. But this one will be one of those bizarre transactions that take place in an odd marketplace known as the Twilight Zone."
William J. Feathersmith, the 75-year-old president of a large corporation, is self-centered, sadistic, and bored with success. Feathersmith talks with the janitor, Mr. Hecate, who comes from the same small town—Cliffordville, Indiana. Feathersmith and Hecate have been working in the same building for 34 years. Feathersmith dreams of returning to Cliffordville and starting life anew.
Feathersmith then meets "Miss Devlin" in a travel agency in his own building on the 13th floor. Though it is never stated outright, Feathersmith quickly comes to realize that Miss Devlin is the devil (or is, at least, working in his service). Excited by the implications, Feathersmith offers to sell his soul for the chance to start life over. Miss Devlin informs him that, because of all the evil deeds he has committed over the course of his life, he is irrevocably bound for Hell and his soul is no longer his to offer. Miss Devlin proposes that Feathersmith should make a monetary payment in the form of almost all his liquidated worth leaving him with a little over $1,400. Because he knows where oil has been found and which investments have succeeded and which have failed in the last 50 years, Feathersmith agrees and is soon transported by train to Cliffordville in the year 1910, looking 30 years old.
Back in 1910 Cliffordville, he uses $1,400 to buy 1,400 acres of land which he knows to contain deposits of oil. He forgets, however, that high-power drills to access the oil have not been invented yet. Feathersmith tries to woo the daughter of a rich landowner, but he is startled that, rather than being the beauty he remembers, she is actually quite homely. He tries to "invent" a self-starter for automobiles, but he doesn't know how to design one. Eventually, Feathersmith realizes that the Devil did not regress his physical age; he is still 75 and merely appears to be 30, meaning that he will die before he is able to capitalize on his purchase. Feathersmith accuses Miss Devlin of cheating him by altering the past, but she retorts that this is all as it was, he just chose to remember it differently. She needles him that he has lived off the work of others and is unable to create anything himself.
Miss Devlin gives him one chance to go back to the future by boarding another train, but the price of the ticket is $40. Despite having no money left, Feathersmith agrees, selling the deed to his land to a young man in Cliffordville to afford the fare. Feathersmith is transported back to the future, where he discovers that the young man to whom he sold the land is Hecate. Because of Feathersmith's actions, Hecate is now the president of the corporation and Feathersmith is his janitor.
"Mr. William J. Feathersmith, tycoon, who tried the track one more time and found it muddier than he remembered - proving with at least a degree of conclusiveness that nice guys don't always finish last, and some people should quit when they're ahead. Tonight's tale of iron men and irony, delivered F.O.B. from the Twilight Zone."
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