- Morton: How does it feel sitting behind that desk, Frank?Frank: Almost like holding a gun... only much more powerful.
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- In the Justice League of America Weird West Elseworld Justice Riders, Maxwell Lord is a ruthless railroad baron who uses alien technology to create robot railworkers, and employs Felix Faust to wipe out any town that's in his way. Unfortunately for him, one of these towns is the home of Sheriff Diana Prince. Lord eventually fights the Riders as Lord Havoc, in Steampunk Powered Armour.
- Sir Harry Percival in Cat Ballou (villain)
- Morton in Once Upon a Time in the West (villain)
- A Railroad Baron is seen briefly in The Wild Bunch and portrayed as worse (somehow) than the eponymous Bunch themselves.
- McCabe in McCabe & Mrs. Miller is attacked by agents of a crooked railway baron's company after refusing to sell land to them.
- Parodied quite humorously by Mel Brooks himself as the corrupt governor who stands to profit from directing the railroad through the town in "Blazing Saddles".
- It was, in fact, done by State Attorney General Hedy Lamarr.
- The Railroad Colonel (that's what the character is credited as) in the movie Rustlers' Rhapsody.
- Tom Garner in The Power and the Glory (tragic hero)
- A Sherlock Holmes novel by Larry Millett had one of the big (real-life) railroad barons in Minnesota as Holmes's ally and, possibly, client.
- Harvey Cheyne's father in Captains Courageous averts most of the stereotype. He is treated as an often ruthless man but a more or less sympathetic one.
- Dagny Taggart of Atlas Shrugged is pretty much the inverse of every stereotype of the Railroad Baron. Her railroad's founder, Nathaniel Taggart, is the idealized version of the stereotypical Railroad Baron; Ayn Rand probably modeled him on James J. Hill.
- Dagny's brother, James Taggart, almost fits this trope. However, due to his incompetence, Dagny (for the most part) runs the company, while he seeks political influence.
- The Fat Controller in The Railway Series (Sir Topham Hatt in Thomas the Tank Engine) fits the stereotypical appearance as a stout man in a top-hat but, while stern and businesslike, is also sympathetic to his engines and certainly not evil.
- Augustus Melmotte, the villain of Anthony Trollope's novel The Way We Live Now. Appears to have been based in part on real life railway promoter George Hudson (see below).
- While not literally a railroad baron, in the novel Going Postal, Reacher Gilt is definitely a clacks baron (clacks is like a telegraph) and very much dresses and acts the part.
- Raising Steam: Harry King becomes the Disc's first Railroad Baron, much to his delight, as it allows him to leave a legacy other than his night soil business.
- The second series of Bleak Expectations features Emmett Sternbeater, who dupes Pip into building an entire railway network to pursue Gently Benevolent. Along the way, numerous idyllic English villages, orphanages and butterfly sanctuaries are levelled, and dozens of workers killed, all in the name of "progress".
- Most of the railway owners in the Deadlands roleplaying setting are pure evil (one of them uses a zombie workforce, the other one uses evil witches as enforcers, the third one is a Mad Scientist, the fourth one is basically a Fu Manchu ripoff).
- There are several non-combat games revolving around a group of players choosing either to compete or to co-operate in driving strategic railway lines across North America. effectively the players take the roles of rail speculators and can come put at the end as either very rich or very bankrupt.
- This trope is the reason why some of the properties in Monopoly are railroads.
- Becoming one is the goal of Railroad Tycoon. Some campaigns even have you play as one of the Real Life barons.
- Thomas Magruder, from the video game Gun. Big Bad, but is only using his railroads to find an enormous gold deposit that would make him incredibly wealthy and powerful.
- The Fat Controller of Thomas the Tank Engine.
- The Fairly Oddparents: In "Dad Back in Time", Timmy learns that once of his ancestors, Ebenezer Turner, was offered a chance of becoming a railroad baron but turned it down because he thought trains were just a fad. As a result, Ebenezer became the town crier and spent his life crying over the lost opportunity and Orville Buxaplenty became the town's local railroad baron. Timmy wishes Ebenezer had accepted the offer and it creates a timeline where Timmy's parents carelessly destroyed the town with their trains.
- Cheryl/Carol in Archer is an heiress of the Tunt family, an expy of the Vanderbilts (see below) in owning a large railway system, a mansion and opulent hotel in Midtown Manhattan, and "several Cornelii".
- James J. Hill: Owned and directed the building of the Northern Pacific and the Great Northern. Earned the nickname "Empire Builder" which was applied to a GN passenger train. NP and GN also co-owned both the Chicago, Burlington & Quincy and the Spokane, Portland & Seattle. The government wouldn't let him merge these 4 roads into a mega road until 1970.
- Cornelius "The Commodore" Vanderbilt (so called because he also owned a vast steamboat network as well). This is also why the sports teams of Vanderbilt University (which is named after him; he provided the then-huge million-dollar endowment) are called the "Commodores." The guy never thought much of his trains however, and he kept referring to them derisively as "them things that go on land".
- Jay Gould manipulated stock shares to keep his Erie Railroad from being bought out from under him, almost single-handedly crashed the US economy in 1869 in an attempt to corner the gold market, and boasted that he could "hire one-half of the working class to kill the other half" when workers of another of his railroads went on strike. No surprise that he was considered the most hated man in America.
- Diamond Jim Fisk, a business partner of Gould.
- J. Pierpont Morgan, though better remembered for the banking house that still bears his name today, invested heavily in railroads, and did so much to reorganize and merge lines that the process became known as "Morganization." Morgan and Hill's Northern Securities railroad trust was the target of Theodore Roosevelt's first major antitrust lawsuit.
- E. H. Harriman: Owned the Union Pacific and the Southern Pacific.
- Up in Canada, they have William Cornelius Van Horne, for whom there's a bit of a Broken Base. Some see him as a voice of reason and restraint in the otherwise muddled CPR project (after earlier barons caused a bribery scandal with the drunken, womanizing prime minister) and for actually finishing the damn Canadian Pacific Railway; to others he's a villain for the CPR's treatment of immigrant workers (they had to spend most of their income on food and lodging at the worksite, and ridiculously dangerous tasks).
- George Hudson is probably the best known example in British history. Starting life as a humble draper's assistant in York, he came to embody the 'Railway Mania' of the 19th century. At the height of his power and influence he lauded as the 'Railway King', was elected as Lord Mayor of York and MP for Sunderland, and was close friends with such luminaries as George Stephenson and the Duke of Wellington (Hudson's advice on railway investments made the latter a huge fortune). His somewhat iffy business practices (he relied heavily on bribery) led to his eventual disgrace and downfall, though he retained several influential friends who supported him in his final years. One of the models for the fictional Augustus Melmotte in The Way We Live Now; interestingly, author Anthony Trollope was an acquaintance of Hudson's nemesis George Leeman, who led the investigation into Hudson's dealings.
- Collis P. Huntington, Mark Hopkins, Leland Stanford (who founded Stanford University in memory of his deceased son) and Charles Crocker, the "Big Four" of the Central Pacific Railroad. They controlled California state politics in the late nineteenth century. For a few years in the early twentieth century, Huntington's son Henry controlled all the trolley lines in Los Angeles.
- Henry Morrison Flagler, whose Florida East Coast Railway did a lot to establish Florida as a tourist destination and basically created the city of Miami.