Matthew McConaughey
Credit: Courtesy Matthew McConaughey
It's 1980, and Big Jim McConaughey, a traveling oil-pipe salesman based in Longview, Texas, has to collect a payment from a client in Houston, a good 210 miles away. He brings along the youngest of his three sons, 11-year-old Matthew. Big Jim asks Matthew to put on his nicest jeans and his shiniest boots. They make the trip in five hours, pulling up to an imposing high-rise. Big Jim calls upstairs. The client's secretary says he's not around.

But this dude's been dodging calls for weeks, so Big Jim takes Matthew up the elevator. They walk past the secretary into the client's office, where the guy's sitting at his desk. Big Jim introduces his son. Big Jim is a physically imposing man – he played college football and was drafted by the Packers, though he never played a down – but he still figures that it's going to be a lot easier to collect with the kid in the room.

That run works so well that Big Jim brings Matthew on a half-dozen more trips. They drive to Oklahoma, Louisiana, Mississippi, and all over Texas. One time they stop in New Orleans for a shrimp festival. Another time, Big Jim slinks behind a low-rent Louisiana strip mall and buys a titanium Rolex from a guy selling appliances out of the back of his truck. "I thought that was cool, man," McConaughey says now, decades later. "Getting out of the backyard and seeing these trails my dad cut. Seeing people he'd met along the way. He always said, 'What's out back? I know we're way off road, and we're dealing with some shady stuff, but I want to see stuff that's even shadier.' "

Big Jim was 41 when Matthew was born – a surprise baby – and these trips bring them closer, some of the best times they have together as father and son. Big Jim lets Matthew play navigator. They get a 12-piece bucket of Kentucky Fried Chicken and eat the whole thing. When they're done, they spray the dash with Windex and wipe off the grease with paper towels. They talk about "life and chicks," and Big Jim, a passionate man who would divorce Matthew's mother twice and remarry her twice, gives his son some advice.

"Now, you're getting to the age where you're gonna start messing around with girls," he says. "So here's what you've got to follow. You're going to get close, you're going to get intimate, whatever. If you ever make a move, whether it's for a kiss or touching her down there, and you feel the slightest bit of resistance, stop. A lot of times, after you stop, they're going to then say, now it's okay. Don't. That time, that day, that's as far as you go."

This advice will pay dividends for the future Sexiest Man Alive. "It's a great lesson," McConaughey says. "You do that, and you know what? Women do come back. They say, what? Nobody stops! They want to go out with you again. And eventually you don't have to stop." He looks forward to sharing this with his own son when the time is right. Road trip wisdom, he says, should be passed on.