Jefferson Archer became a trucker at a young age, after the death of his parents. He put his dreams on hold in order to take care of other responsibilities like the welfare of his brother, Ulysses. He began to feel resentment which eventually turned to hatred, and Jefferson pursued supernatural means to restore his youth. Salvation soon came for him in the form of alien beings in search of truckers to pilot their star ships. Mistaking Jefferson for Ulysses, the aliens outfitted his truck with advanced technology, yet Jefferson spread a rumor his abilities came from demons. Changing his identity to the Highwayman, he became the scourge of truckers everywhere. Jefferson attempted to repeatedly end his brother's life - even hired agents Midnight and Baron von Blimp to do his bidding - but Ulysses consistently stopped them. Eventually, the aliens learned of their blunder and arranged for an orbital race between the brothers. Ulysses proved to be the better pilot, and Jefferson crashed his rig into the moon as his final attempt to kill his brother failed. The aliens took Ulysses and sent Jefferson back to Earth.
Sometime later, Highwayman made his false origin become a reality, and the legend continued.
There once was a trucker, normal as can be, and he hauled his loads all over the country. As he got older, he found himself losing more and more jobs to younger drivers who needed less sleep, so they could drive longer. There wasn't a miracle pill the trucker could take, and no amount of praying seemed to do the trick, so he resorted to other means to get an edge. He looked elsewhere for help and wound up making a deal with the devil. From then on, the trucker didn't need to rest, and his Black Rig could outrun any police vehicle on the road. He didn't know fear and would haul the most dangerous cargo through the most treacherous terrain. However, the more he drove, the more of his humanity was lost until only the Highwayman was left. Some think he's only a ghost story, but those unfortunate enough to cross his path not only lose their heads – they lose their souls.
A few truckers found out the Highwayman was all too real when an out of control truck, operated by a headless driver, collided with the truck stop they were in and exploded - killing everyone inside. A short while later, a bus full of people met their end when the Highwayman took their heads and fed them to the demons in the Black Rig's trailer. Unluckily for the Highwayman, a passing Daniel Ketch came across the slaughtered innocents and the Ghost Rider was unleashed seeking vengeance for the dead. The Highwayman had the advantage while inside his hellish vehicle, but Ghost Rider soon found a way to subject the Highwayman to the same type of torture he visited upon others. The Black Rig crashed and overturned having no one to steer it, and Ghost Rider ignited the Highwayman's head and set his truck on fire with it as well. Satisfied vengeance was served, Ghost Rider went on his way.
A few days later, the Highwayman showed his face at another truck stop, still recuperating from his wounds, and looking for a new rig. He started the Highwayman Trucking Company and sent his returned brother on doomed missions to transport hyperspace combustion manifolds, and to transport dead souls out of Hell via an ice bridge.