The episode opens with a cluster of iHeartRadio network cross-promotions, spotlighting Raiders of the Lost Podcast (interviewing Ryan Gosling and diving into film classics), Podlandia: AO Rewatch (Carrie Brownstein and Fred Armisen revisiting Portlandia episode by episode), and Everyone Watches Women's Sports (hosts Ari Chambers and Sam Jay breaking down the biggest stories in women's sports). Josh then appears briefly in host mode to frame the Selects pick: the 2023 Stuff You Should Know episode about the very first automobile road trip across America. He teases it as a rare, feel-good historical story — two guys, a dog, long odds — and invites listeners to enjoy.

Josh and Chuck launch into the episode proper, with Chuck immediately flagging that he spent the whole research phase waiting for something to go wrong or someone to turn out badly — and it never happened. Josh declares it a 'humdinger.' Both hosts tip their hats to researcher Ed and, through Ed, to Ken Burns, whose PBS documentary 'Horatio's Drive' is described as a wonderful, highly recommended watch. Chuck lingers on the cast: narrated by the incomparable Keith David and featuring none other than Tom Hanks recreating Horatio Jackson's diary letters, which immediately makes the listener predisposed to love the man. Dayton Duncan, who wrote the book on the drive, is also acknowledged as a primary source.

To understand why a cross-country car trip in 1903 was considered borderline insane, Josh and Chuck lay out the numbers: the United States had 2.3 million miles of roads, of which a mere 150 were paved — all of them in big cities ^{[1] — Josh "150 of 2.3M road miles paved: In 1903, out of 2.3 million miles of roads in the United States, only 150 miles were paved, and all of those …" 07:17 Play} . The rest were rutted, dusty, muddy tracks barely suitable for horses. There were approximately 14 million horses in the country and around 8,000 cars. The average American rarely ventured more than a few miles from home. Long-distance travel meant the train; local travel meant the horse. Even east of the Mississippi, where maps and guidebooks existed, directions were given by landmarks ('Turn right at the old stone horse trough'), because roads had no names or numbers. Out west, there were essentially no maps at all. Cars were expensive — the cheapest cost more than the average American's annual wage — and widely considered a fad that would never displace the horse or the train.

Car manufacturers quickly realized that a successful coast-to-coast drive would be priceless publicity. The first real attempt, in 1899, starred John and Louise Davis in a Duryea car sponsored by the National Motor Carriage Company. It was a PR catastrophe: they were beaten to Syracuse, New York, by a one-armed bicyclist who had been given a 10-day head start. Press coverage evaporated after Chicago. Then in 1901, Winton himself — with his publicist — tried heading from west to east (smart: tackle the hardest terrain while the car is fresh). His undoing was the Nevada desert, where sand clogged carburetors and oil systems and ultimately bogged them down entirely. Yet both failures generated enough publicity to confirm: whoever actually completed the crossing would be famous.

The star of the story is Horatio Nelson Jackson: a doctor who contracted tuberculosis, gave up medicine, married the wealthy Bertha Richardson Wells (whose New England family made their money in celery compounds), and settled into a life of comfortable adventure. By 1903 he was a devoted car enthusiast and collector. At the University Club of San Francisco, when fellow members dismissed automobiles as useless, Jackson defended their honor with a $50 wager — worth about $1,500 at the time — that he could drive from San Francisco to New York in under 90 days ^{[1] — Josh "$50 bet sparked the road trip: Horatio Nelson Jackson wagered $50 (about $1,500 in 1903 value) at the University Club of San Francisco that…" 16:08 Play} . The bet was accepted on the spot. Four days later he was on the road, having only just purchased the car. His wife, whom he addressed in letters as 'My dearest Swipes,' took a train to Burlington and wished him well. The letters home, voiced in the documentary by Tom Hanks, paint a picture of a warm, loving couple — and a man who approached the whole enterprise with infectious good cheer.

On Crocker's advice, Jackson bought a 1903 Winton touring car — the same brand that had attempted the crossing in 1901, which was a smart endorsement of the car's capability. The price: roughly $3,000 in 1903 dollars (about $100,000 today), for a used vehicle, because it was the only one available ^{[1] — Josh "Winton touring car: 20 horsepower: The 1903 Winton touring car Jackson bought had a 2-cylinder chain-drive engine producing just 20 horsepo…" 20:07 Play} . Jackson named it the Vermont, after his home state. The car was bare-bones: a two-cylinder chain-drive engine with 20 horsepower (less than a John Deere X300 riding mower), no windshield, no roof, no doors, and a top speed of 30 mph it would rarely approach. They ripped out the back seat and loaded it with a pulley system (the block and tackle that would save them dozens of times), a Kodak camera, guns, ammunition, rope, a cooking kit, sleeping bags, and a shovel. Sewell Crocker, ten years Jackson's junior at about 22, was the unsung hero — a small-engine mechanic who would spend the trip fixing the clutch, sourcing spare parts, and occasionally cycling dozens of miles on a borrowed bicycle just to fetch gasoline.

Jackson had barely gotten underway when the corporate cavalry arrived. Two months after his May 23 departure, Packard sent a team that had everything Jackson didn't: a dedicated mechanic, gasoline pre-stocked at intervals along the route — essentially a private chain of gas stations — and the full weight of a car company behind them. Oldsmobile followed a month after that with a similarly equipped expedition. The contrast was stark: Jackson had thrown the trip together in four days with a used car and a single friend, while Packard's Tom Fetch had a full support infrastructure. Yet Jackson's version of events is the one history remembers — partly because it was purer, partly because it was more fun, and partly because of a dog named Bud who had not yet joined them.

May 23, 1903 was a warm Saturday that turned rainy in the afternoon — and that didn't stop Jackson and Crocker from heading east. The San Francisco Examiner ran a brief note about a horseless carriage attempting a sea-to-sea journey; the Chronicle ignored it entirely. Almost immediately, a tire blew out, setting the tone for the western leg. Tires were a constant headache: the roads were brutal, replacement tubes were nearly impossible to find out west (because almost no one had cars), and the two men learned to stockpile used tubes whenever they hit a town. Gear fell off the car at regular intervals — cooking utensils, multiple pairs of Jackson's eyeglasses — lost forever somewhere back along the trail. And then there was the question of where to go: rather than cutting straight east, they made the critical decision to head north through Oregon and into Idaho, adding hundreds of miles but sidestepping the Nevada desert that had already doomed Winton.

The western leg of the journey reads like a compendium of everything that could go wrong. The Cascade Mountains presented cliff-side roads barely wide enough for one vehicle, shared with stagecoaches and horses, with no room for error. The brakes were inadequate for steep descents; the clutch failed repeatedly and Crocker repaired it over and over again. When they ventured onto railroad right-of-ways — often the only flat, clear surface available — they drove across railroad bridges in an open car topping out at 30 mph, hoping no train was coming (an experience Josh compared to the famous bridge scene in Stand By Me). Locals, rarely having seen a car, were unreliable guides: one woman on horseback deliberately misdirected Jackson and Crocker down a dead-end driveway miles long, just so her family could see an automobile. They came back, met her again, asked why, and heard the cheerful explanation — and apparently accepted it without anger. On their worst day, the block and tackle was deployed 18 times to free the car from mud, ditches, and rivers ^{[1] — Chuck "Block and tackle used 18 times in one day: On their worst day, Jackson and Crocker had to use their block-and-tackle pulley system 18 times…" 34:43 Play} .

The hosts pause for a mid-episode ad block carrying the same rotation of iHeart network cross-promotions heard in the cold open: Everyone Watches Women's Sports with Ari Chambers and Sam Jay; Portlandia stars Carrie Brownstein and Fred Armisen promoting Podlandia: AO Rewatch; and a Spanish-language segment for Suite 305 with Lele Pons. No paid sponsor integrations appear in this episode.

An offhand joke about Segway inventors leads to an impromptu mid-show fact-check when Josh confirms, live, that Jimmy Heselden — then owner of the Segway company — really did die at 62 after riding off a cliff on his own Segway in West Yorkshire, as BBC News reported. It's the kind of fact both hosts agree sounds like urban legend but turns out to be entirely real. Chuck then layers on a similarly surreal story about Fabio getting hit in the face by a duck on a roller coaster, which Josh cannot confirm with photographic evidence — the best he can find is a before-and-after of Fabio entering and leaving the roller coaster station, face bloody, rather than the moment of impact.

Chuck pauses to correct what might be a misleading impression: yes, the trip was hard, but Jackson and Crocker were not suffering. They had no rigid schedule, stayed in hotels and private homes, drove about two hours at a stretch, and by all accounts were having a wonderful time seeing landscapes few people had ever witnessed. Jackson had money; Crocker was well-paid. The spirit was adventure, not endurance. Then came Bud. In Caldwell, Idaho, after doubling back for a forgotten coat, they met a man with a white pit bull who wanted to join the journey. Jackson paid $15 (about $500 today) for the dog ^{[1] — Chuck "Pit bull Bud joined in Caldwell, Idaho: A man in Caldwell, Idaho gave Jackson and Crocker his pit bull named Bud to serve as trip mascot; J…" 46:51 Play} . The crew fashioned leather doggles to protect Bud's eyes from the wind and dust. Bud took to the car immediately — learning to read the road, bracing for bumps — and when towns ahead got wind that there was a dog in the car wearing goggles, public interest in the whole enterprise exploded.

By Wyoming, Jackson was writing home with confidence that they would make it. Once they reached Omaha, the trip shifted from ordeal to victory lap: flat plains, better roads, railroad right-of-ways they could cruise, and a steady march through Omaha, Chicago, Indianapolis, and Cleveland. On their best days they covered around 70 miles — not fast by modern standards, but impressive for a car with 20 horsepower on 1903 roads. In Cleveland, they passed through the home of the Winton Motor Carriage Company, whose founder had tried and failed at this same journey two years earlier. Winton, now aware that one of his own cars was close to completing the crossing, offered Jackson sponsored fuel drops and a technician escort for the home stretch. Jackson declined. He'd started this trip with no backing and he intended to finish it that way.

The final stretch threw one more surprise at them: near Buffalo, New York, the car hit what Jackson described only as 'a hidden obstruction' and all three — Sewell, Horatio, and Bud — were ejected. Miraculously, none were hurt and the car survived. They kept going. On July 26, 1903, at 4:30 AM, they rolled into Manhattan, having crossed the United States in 63 days, 12 hours, and 30 minutes ^{[1] — Josh "63 days, 12 hrs, 30 min crossing: Jackson and Crocker completed the San Francisco to Manhattan drive in 63 days, 12 hours, and 30 minutes, …" 51:50 Play} . Press, Winton representatives, and Bertha — 'Swipes' herself — were there to greet them. Jackson had won his bet. He never collected ^{[2] — Chuck "He never collected on. Oh, I was curious about that. He didn't? Nope. What a stand-up guy." 52:47 Play} . Whether from magnanimity, exhaustion, or simply not wanting to make the return trip any time soon, the money stayed where it was.

The hosts close with a quick tour of what came next. Bud lived out his days on the Jackson farm in Burlington, Vermont — not a euphemism, Josh confirms. Jackson went on to have a rich second act: business ventures, military service in WWI as a decorated veteran in his 40s, an unsuccessful run for governor of Vermont, and the eventual donation of the Vermont car and Bud's famous doggles to the Smithsonian. Sewell Crocker, the unsung genius who kept the car running for 3,000-plus miles, was sent to Mexico during the revolution, contracted an illness, and died around age 31 in 1913 — the one genuinely sad note in an otherwise joyful story. Six years after Jackson, Alice Ramsey and three friends completed the first women's cross-country drive in 59 days, sponsored by Maxwell-Briscoe ^{[1] — Chuck "Alice Ramsey completed trip in 59 days (1909): Six years after Jackson, Alice Ramsey and three friends became the first women to drive cros…" 54:21 Play} — covered extensively by a press that described them primarily as 'pretty.' And roughly 30 years after Jackson, Erwin 'Cannonball' Baker made the crossing in 54 hours, a record that Car and Driver magazine commemorated in the early 1970s with the event that became the Cannonball Run ^{[2] — Josh "Record later cut to 54 hours: About 30 years after Jackson's trip, Erwin 'Cannonball' Baker set a cross-country record of 54 hours from New…" 55:36 Play} .

The final minutes of the episode are given over to iHeart network promos: Raiders of the Lost Podcast returns with film interviews and deep dives; Podlandia: AO Rewatch reprises the Portlandia cast reunion pitch; and Everyone Watches Women's Sports closes things out with Ari Chambers and Sam Jay. The standard Stuff You Should Know / iHeartRadio production credit plays out, and Chuck delivers the closing 'Guaranteed Human' tagline.