Alves had never road-tripped before she met McConaughey. "I don't know anybody who's better to travel with than him," she says. "He knows how to do things, and if he doesn't, he can take a deep breath and try to figure out how to handle it. He can pretty much deal with every situation."
On New Year's Eve, McConaughey's friend Mark Gustawes catches up with them, camping by an obscure river in East Texas. "He could pack up his family and get on a jet and go to the South of France, but he chooses to be in the middle of nowhere," Gustawes says. "He finds the beauty in real simple things: rocks and twigs, armadillo and deer. That's his heaven, on the road."
Gustawes, who has been on countless road trips with McConaughey, says it's hard to stick to the highway with him. He prefers the feeder roads – the more obscure, the better – the same way it was with Big Jim. "He enjoys pulling in to the worst motel possible, just to have the experience," Gustawes says. "We get out and wander around in the town and connect the dots. You go out to dinner, ask what's happening, and then you end up at a weird carnival."
During one trip Gustawes joined him on, from Texas to L.A., McConaughey decided he was sick of seeing El Paso, so they took a long detour through rural New Mexico. This was 1999, well after McConaughey had become famous. They pulled into a motel and saw a flyer for the New Mexico Karaoke championships. McConaughey just had to see what that was about. They ended up competing, but not winning, and then the town's sheriff bought them dinner at 3 am.
It's all part of what Woody Harrelson describes as McConaughey's "never-ending quest" to absorb as much of humanity as he can. "A lot of people obtain his type of success, and they just retreat," Harrelson says. "They run for shelter. He hasn't let that amount of notoriety mess with his ability to connect with people. He's always going out, seeing the world, meeting chiefs from some remote tribe in Tanzania."