Many of us pilot hoopties that’d have a tough time making a cross-country journey. I’d bet on one of the four cars in my driveway. Rewind to 1903, and the idea’s pure insanity.
Enter Horatio Nelson Jackson, a case study in why it’s ok to be richer than God. Nelson practiced medicine for a few years before marrying into enormous wealth (his wife’s family made their fortune from Payne’s Celery Compound, a concoction that was 20% alcohol by volume–<i>yummy!</i>). While whiling away at the day at The University Club in San Francisco, he made a $50 wager (almost $1200 today) that a car could make a cross-country journey.
Jackson and co-pilot/mechanic Sewall Crocker set out in their Winton Tourer, titled the Vermont on May 23, 1903. Their journey reads like a rookie LeMons showing: they blew through their only spare tire 15 miles in. From Wikipedia:

Going northwards out of Sacramento, the noise of the car covered the fact that the duo’s cooking gear was falling off. They were also given a 108-mile misdirection by a woman so that she could send them to the spot where her family could see an automobile.
The rough trek towards Oregon required them to haul the car across deep streams with the block and tackle. Somewhere along this route, Jackson lost his glasses. They were also forced to pay a $4 ($85.21 in 2005 dollars) toll by an entrepreneur in order to cross his property. When their tires blew out they were required to wind rope around the wheels. Jackson did manage to find a telegraph office and wired back to San Francisco for replacement tires to be transported to them along the journey.
Reaching Alturas, California, Jackson and Crocker stopped to wait for the tires. They offered locals rides in the car in exchange for a “wild west show”. When the tires failed to materialize, however, they continued on after a three-day wait.
On June 6, the car broke down, and they had to be towed to a nearby ranch by a cowboy. Crocker made repairs, but a fuel leak caused them to lose all of their available gasoline, and Jackson rented a bicycle to travel 25 miles to Burns, Oregon for fuel. After suffering a flat tire on the bicycle, he returned with fuel, and they returned to Burns to fill up.
On June 9, outside of Vale, Oregon, the Vermont ran out of oil. Jackson walked back to the last town to get oil, only to discover eventually that they had been stopped only a short distance outside of Vale. The next day they arrived in Ontario, Oregon, where supplies waited for them.

Somewhere along the way, they picked up Bud The Dog. Bud, an early pit bull, loved the trip and got more than his fair share of attention as they rolled (clunked?) through various towns, headed eastward. While crossing alkali flats, the dust irritated Bud’s eyes to the point that they fitted him with his trademark goggles. Alas, my Bud the dog seems averse to such eye wear (but does love going for a ride!)
They eventually made it to New York on July 26th, setting the first coast-to-coast drive record at almost 2 months. On the drive from New York to his home in Vermont, Jackson made it within 15 miles of home and the Winton broke down for the Nth time. His brothers, each in their own car, came out to help him. After getting him roadworthy, both of their cars broke down, so Jackson towed both of them back. as a fitting bookend on the story, once home, he broke the main drive chain of the car on his way into the garage. That was the first time it broke.
The trip was awesome enough to warrant both a book by Dayton Duncan and a PBS documentary directed by Ken Burns, both titled Horatio’s Drive. For the young hoon your life, there’s Jackson and Bud’s Bumpy Ride. Be sure to check out the interactive map on the PBS site for highlights from the Journey.

Pictures and most info sourced from Wikipedia.