And just like his long-lost relative, James has a renegade reputation, too, that he's riding all the way to the bank. He builds motorcycles, custom-built choppers that are cool, pricey, and very fast, Correspondent Vicki Mabrey reports.
James says his choppers can reach speeds of 140 miles an hour.
Why? "What if you're late," says James, who has no excuse to be late, not the way he rides.
James' hometown, Long Beach, Calif., is a blue-collar city that fits him like a leather glove. There are speed limits and helmet laws here, but just like his outlaw relative, this Jesse lives by his rules and rides the roads as if he owns them.
What thrill does he get from weaving in and out of traffic?
"When I'm sitting on my bike, and it's loud, and shaking my hands, and it's hurting my ears, and the wind is loud. I mean, that's my soul. That's what makes me happy. To do that, and get really crazy, and you're riding and you're hauling ass somewhere," says James.
"And then, to do it, and I look down, and the reflection of a perfect gas tank that I made. And I made the whole bike by hand. And something that I made by hand gave me that feeling? No one can feel that but me."
Forget Peter Fonda and "Easy Rider." Modified or chopped motorcycles from the '60s have given way to rockets on two wheels. James builds West Coast Choppers, and they have more horsepower than some cars, custom paint that costs more than $1,000 dollars a gallon, and chrome wheels cut by computer.
What's the difference between a Harley-Davidson and a West Coast Chopper?
"You can't tell by looking at it? They blow it away. What are you talking about," says James, laughing. "Speed, handling, stopping, the weight. But, you know, some people, their ultimate bike might be a Harley, you know? They're just dorks. And it's my goal to make everybody cool, or just 20 people a year."
And he means only 20, because that's all the custom bikes he builds in a year. Why so few?
"Well, if they're expensive and hard to get, and they're really, really bitching and cool and clean, they're always going to be cool," says James.
Each bike goes for up to $150,000. For that, you get a machine that's considered one of the best-built motorcycles in the world. Some consider them works of art -- so much so that the Guggenheim Museum in New York wanted to exhibit them. But James said no.
"You can only sit there and look at it for so long before you're gonna want to ride it," says James. "They're meant to be ridden."
"Everyone wants to see them," says Mabrey.
"I don't know. I'd rather be doing a wheelie on it," says James. "Guggenheim, schmugenheim."
Mabrey hoped she could go out for a ride, but since James' bikes are custom- built, he doesn't build a backseat on his bike.
"Most of these customers of mine, I don't think they're getting these bikes because they want to spend more quality time with their wife or their girlfriend or whatever," says James. "I think they're getting them because they want to get the hell away, you know?"
His choppers have become the ultimate boy toy for the rich and famous – and celebrities like Shaquille O'Neal, Keanu Reeves, and Kid Rock are part of this new James gang.
In southern California, the land of reality TV, it didn't take long to recognize a gold mine. Producer Thom Beers spotted James in his garage and had an idea for a different kind of TV show, one that needed a macho mechanic as host.
"It's like Brando in the old days. There was just something bubbling underneath that guy, you know. And that's what he's got," says Beers. "He's got that thing where you just, you don't know if he's going to give you a big hug or kick your ass."
James was perfect for the lead in a show called "Monster Garage." It first aired five years ago, and has one of the biggest audiences on the Discovery Channel. Every week, James and a team of mechanics take a perfectly good vehicle, rip it apart, and transform it into something unimaginable. According to the rules of the show, they have five days to complete the challenge.
In the first episode, the plan was to convert a Ford Mustang into a lawn mower that could cut grass at 70 miles an hour. Why? Just to see if they could.
"I told him, I said, 'Jesse, the first thing we gotta do is this. Let's just make a lot of noise, and make a big mess. Because if it doesn't work, at least it'll look cool. OK?'" says Beers. "So it takes off, and all of a sudden, I look and it's like 50, 60, 70 miles an hour. … It was like, 'Oh my God. It works!' It's like, 'It's alive!'"
Since then, there have been more than 60 transformations. Some examples: a school bus that turns into a pontoon boat; a police cruiser that makes donuts so officers never have to leave their car for a snack; and a Porsche-turned-golf-ball-retriever that shoots balls back at the golfers.
Monster Garage showcases everyday mechanics as more than guys who can turn a wrench. "If we do something that's totally easy, and I know we can do it, it's a boring show," says James, who's for the season finale.
"We're gonna do a Jaguar, like a new XI, the all-aluminum, because they're light, and make it fly," says James. "Like 1926 Popular Mechanics said the year 2000, we're supposed to have flying cars. And no one did it yet. So I'm gonna do it in five days."
But sometimes the clock runs out, or the cars turn out to be clunkers, like a Mazda they tried to turn into a dune buggy. After five days, it didn't work, and that's when things got ugly. So James hauled it out to the Arizona desert, and with the help of a machine gun that fires 3,000 rounds a minute, he put the Mazda out of its misery.
"You don't wanna be around me, like, the next day or so after that," says James. "I take it serious, and five is my record."
His bulldog attitude has won him millions of fans, but he still drives himself to work every day. And waiting outside his garage like a welcoming party are Jesse fanatics.
"This is the tripped-out thing about this whole place, why it's so crazy -- that I'm the only person on TV every week with a popular show, that you can call where they work," says James.
"And then, that I'm related to Jesse James, which has, like, tons of kinfolk and stuff like that, it just compounds it."
But all this attention is making James very rich. If you can't afford a custom bike, you can still make a motorcycle look like a West Coast Chopper with Jesse's fenders and parts. Or if you just want to look like James, he has a line of merchandise through Wal-Mart that fans are snapping up to the tune of $200 million a year, which is a lot more than he can make welding motorcycles.
But it doesn't stop there. He's also done commercials.
It's a long way from James' teenage years in Long Beach, Calif., where he was arrested for stealing cars. His parents were divorced when he was 5, and he grew up poor, and hung out with a tough crowd.
He says his father made him work for everything he got: "My dad worked me like a dog when I was kid. From 8 years old, I was an integral part of his business and working, and you know, made me. I mean, if you're hungry, make yourself something to eat. If you need clean clothes, wash your own damn clothes. If you want to buy something, earn the money and go buy it."
"Seriously. And you know, I hated it," adds James.
What did it teach him? "That my dad's a jerk," says James, laughing. "No, I think it taught me to be independent and never expect a handout and never wait for anybody to hand you anything in any aspect of my life."
And it's a work ethic that's always stayed with him. When James was starting out, he never borrowed a dime for his business. What began in the corner of his mother's garage now takes up two city blocks, with a warehouse reserved for his fleet of cars, including the neighborhood's only Ferrari and Lamborghini.
But one of his favorites is a slightly modified '54 Chevy. He gave it the look of a low rider for an episode of "Monster Garage," with special shocks that only James could love.
"It's just kinda cool to pull up somewhere and, bam, you drop it all the way down," says James. "And people are, they can't steal it because they have to drag it on the frame. It's like the world's best 'Club.'"
James says there are two types of people in the world: those who can weld and those who can't. He claims to be nothing more than a glorified welder, but he's more complicated than that. He's an entrepreneur who's transformed a love of motorcycles into a business worth millions of dollars, and he built it by himself, with what he calls "sweat equity."
For James, long days under the hood aren't work; they're time in boy heaven. And life's not too bad outside the garage. He's dating actress Sandra Bullock.
"I'm not talking about her," he tells Mabrey.
"You're getting nervous now, aren't you," says Mabrey, laughing. "Are you happy?"
"Yes, extremely," says James. "I mean, look, I'm so lucky. Look at my life. I get to weld stuff every day, and try to break it, and take expensive cars out and pound on 'em, and then jump in my '54 and go home."
that James was working on? He built it, and the first test flight is scheduled for Friday at Kitty Hawk, N.C.