True Road Trip Tales

Coveting is desire, fantasy, envy, and impracticality all wrapped up together. Once you begin to covet something, the only way to put out that fire is to divine a way to get it for yourself. 

Ernie takes his Checker Marathon through the heart of America to the promised land.

In college, if you were lucky enough to have a car to drive, it was often a hand-me-down—the ride that your family had broken in or your brother had nearly driven into the ground before it got to you. And that was all fine: if it was roadworthy, you were way ahead of the game. 

Very few people, save for the future trust funders and frat boys, were driving nice cars. And no one was looking to make any kind of statement. My friend Tim drove a blue 1978 Dodge Monaco that broke down five miles outside of our destination one trip. When the tow truck driver came to our rescue, his first words were, “How do you expect to pick up any puss in that boat?” The salvage yard delivered the final verdict in exchange for $100. That felt like par for the course. 

It’s one of the paradoxes of being in college: all the time in the world but no means to wring the nectar out of life. Then again, there’s always a road trip. It barely costs anything, and as long as there’s a floor to crash on, you’re golden. 

But sometimes the most hastily thrown together plans don’t quite work out, and your vehicle is all you have. A notion to experience Mardi Gras on a whim would fall into that category. The three adventurers in this episode encounter just such as fate, but they had a secret weapon: Big Blue, a 1979 baby blue Cadillac Seville. It was more than a car on that trip; it was a beacon, talisman, guide, protector, and lodging. Big Blue had their back and kept them between the ditches when it mattered most. 

Anyone who’s been to Mardi Gras knows that’s just scratching the surface of the story. Enjoy. 

I’ve remarked from time to time, “He’s a nice guy, but I wouldn’t want to go a on a cross-country road trip with him.” That’s not a damning criticism; it’s more a recognition that the bar is really high for that kind of commitment.

You’ve probably been on a road trip where by the end you wanted to throttle the person next to you. It’s the nature of an extended amount of time spent in close quarters with someone. They may ride the brake unnecessarily. They may take too long at gas stations. They may talk too much. They may be too quiet.

In a real way, it’s not even about them. The construct of the road trip is so exacting that very few people can clear that bar. And the road trip, like hosting the Oscars or trying to follow up a best-selling debut with an offering that doesn’t completely suck, tends to expose the vulnerabilities and proclivities of mere mortals.

The trick to finding the right road trip companion is to be in sync with how they move through life. In short, they care about what you care about and are conscientious enough to give you space—even when space is at a premium. How many people in your life would meet those criteria? You can count ‘em one hand.

This episode is about Brad and George and a dual quest that required 35 days and nearly 9,000 miles to achieve. And it’s about the healing, bonding power of the road trip—even for lifelong friends.

Go here for a full rundown of their itinerary and adventures.

Road trip reawakening

I’m a firm believer in low expectations as a key element of a happy life. When you go into anything fully expecting to have the best time of your life, you’re inevitably disappointed. How often can the stars really align? Examples abound in all parts of life. All the best concerts I’ve seen were in part a product of not expecting much going in. And no victory is sweeter than the upset.

One of the best parts of a road is that the unknown makes it impossible to have well-defined, high expectations. There’s such a huge variance for what could happen that as long as your car doesn’t break down and you have something to report back, you’re ahead of the game. 

Partly for this reason, I’ve never taken a road trip where I did start with a fair bit of excitement and anticipation. Even when you know your traveling company well and the route is set, you never know what conversations and experiences are waiting. “Who knows what could happen?” is a big part of it. 

But what if the prevailing attitude is “Who gives a shit?” There are low expectations, and then there’s the total absence of expectations. 

In this episode, the total lack of expectations was so completely liberating that the result was a life-altering experience. It also features one of the best articulations of why the road trip is so alluring: 

“Once you give into the notion of a road trip, you're suspending time that you knew in the conventional sense. You're suspending deadlines. You're suspending paying bills. All the other shit that makes life a drag is in suspension because you have a new relationship with time. And that relationship is, ‘What are we going to do with it?’ Not, ‘What do I have to do?’ That choice, being able to explore those options and that new sense of time, is extremely liberating.”

This is the story of Rob and Toodles, the ocean and oranges, Widespread and underwear, and plugging back into this whole surreal journey called life.

Burning Man to Vegas

You have to hand it to Las Vegas: over decades, it has established itself as an adult playground where virtually anything goes. If you want the chance to revel in excess and not feel like you have to make any excuses for your choices or behavior, Vegas is the place. Sure, the shops and shows and spectacle and helicopter rides and Hoover Dam lend the city a patina of respectability, but everyone knows its pure decadence is really the draw.

For people who think Las Vegas has too many rules that get in the way of the good time they really want to have, Burning Man is a quantum leap forward. Founded in 1986 as an annual weeklong gathering that celebrates radical self-expression (among other principles), Burning Man has more than doubled in size over the past 15 years. Each August, an entire city is created in the desert, with art installations and attractions. The week culminates in the immolation of a wooden structure—the Man. An unadulterated feast for the senses fueled by lots of people living in the moment in every way imaginable, the fun you can have is limited only by your ability to withstand the pace for seven days amid dust storms. 

As destinations for debauchery, it would be difficult to top these two destinations. So why not plan a wedding in Las Vegas to cap off the week? For Bren and Sally, who hail from Dublin and Leeds, respectively, the whole endeavor gave them a window into a side of America most of us haven’t experienced—and provides us an indelible tale that careens from hope and anticipation to despair before a superhero named Dale saves the day. 

This story encompasses some elements that couldn’t be more American: an annual guy’s trip, college football, a carefully constructed song list, and an RV. Enjoy.

This episode is about chasing ghosts and legends—always a tricky proposition. The legend in question: the crossroads (purportedly at the intersection of Highway 61 and Highway 49 outside of Clarksdale, Mississippi), where a young Robert Johnson sold his soul to the devil in return for prowess on the guitar.

This story has so much we can all relate to—high school friendships, first love, spring break, a wildly ambitious plan, and some indelible life lessons. We said in the first episode that the road reveals. This tale is exhibit A.

Ep 3:

This episode is a love story between a woman, the state of California, and a conversion van. She performed an important service for people in the Midwest: she proved that not only was the trip worthwhile, but also that California was as better than advertised.