Wearing a white T-shirt and blue jeans and sporting a compact moustache, Chris Gay, fully shackled in the back seat of a sheriff's cruiser, stayed mostly quiet as his home state of Tennessee – and the likelihood of a long prison sentence – drew ever nearer.

Coffee County, Tenn., Capt. Donnie Thomas didn't know the diminutive prisoner in the back was one of America's most notorious cons, a man one Tennessee police chief calls "the Cool Hand Luke of the 2000s." The deputy made it back to Tennessee. His prisoner didn't.

Mr. Gay's much-publicized prison-break in 2007 to reach his dying mama's side failed, but only after he led authorities on a five-state, five-day chase that ended with him being arrested driving the country singer Crystal Gayle's stolen tour bus in Florida. Now police around the flyspeck burgs of northern Tennessee are back on full alert after another audacious escape by Gay in Kennesaw, Ga., on Tuesday.

"How people portray him, he's an outlaw," says Michael Douglas, the police chief of Pleasant View, Tenn.

The details of Gay's Houdini-like escape – a wily thief up against a veteran small-town Tennessee deputy – is remarkable for its "Smokey & The Bear" allure at a time when outlaws are found mostly online.

Indeed, with the US firmly entrenched in the Homeland Security era, Gay's criminal, but non-violent, exploits and escapes have made him an unlikely figure: The latest in a long tradition of American counter-heroes, a modern-day Pretty Boy Floyd.

"After 9/11, law enforcement has kind of become omnipotent, but there's a yearning, perhaps stronger than ever, for someone to thumb their nose at authority, and that's why [Gay] is very appealing in his own kind of curious, if somewhat perverse, way," says Stephen Mihm, a historian at the University of Georgia and author of "A Nation of Counterfeiters: Capitalists, Con Men and the Making of the United States."

"Law-abiding folks view these people with perhaps misplaced admiration, but one that has a lot to do with whatever resentments ordinary people might nurse against authority, whether it be a bank or the local sheriff's department," he says.

The Gay story has as many twists and tragedies as the best country song, which is what songwriter Tim O'Brien picked up on when he first read about the case in a small paper in Telluride, Colo., in 2007. The Grammy winner turned the tale into a popular bluegrass song, "The Ballad of Christopher Daniel Gay."

Knowing his mom was dying, the 5-foot-5, 140 pound Gay escaped from a prisoner transport in January 2007 at a welcome center on the Alabama line, exploiting a sodden rain that stymied a team of tracking dogs.

The first leg of the pursuit ended just 50 yards from his mother's trailer in Coopertown, Tenn., north of Nashville, where he crashed a stolen Walmart tractor-trailer into a field and headed for the woods once again. An accomplice picked him up on a nearby back road and took him to Nashville, where he stole Ms. Gayle's tour bus and drove it to a NASCAR track in Florida, littering it with chip bag wrappers and empty bottles.

"What he done was wrong, but he knows his mama don't have long," his mother, Annie, had told the press, after her wayward son had come within 50 feet of her front door. Two weeks after Gay's arrest, Annie passed on.

His mother's death isn't the only tragedy in Gay's life of crime. According to a Maxim magazine article about Gay, he grew up in an alcoholic family and learned to subsist on his own, once as a kid catching and boiling a couple of roosters for sustenance. As his sister, Leann Newman, told Mr. O'Brien, "If you want, he's got stories for songs for days."

Poor, sidelined, and one of millions of witnesses to a world of riches beyond his legal grasp, Gay made use of his diminutive anonymity with brazen cons. A sometime roofer, his thefts grew more audacious as he settled on his preferred targets: heavy construction equipment.

But at the same time, he had a desire to finally break out of his anonymity, to become someone bigger.

"Truth told, Gay didn't particularly want to be invisible any longer," Stephen Russell writes in the Maxim article. "Underneath the need to see his mother, another urge was bubbling up: to finally stand out from the crowd."

With Tuesday's escape, Gay has sealed that wish, becoming what Prof. Minh calls "a classic trickster legend."

"Here it looks like it's curtains for this guy, and what do you know? He outwits his pursuers yet again," he says.

According to published accounts, including those of his wife, Erica Tapola-Gay, Gay is seen by friends as a Robin Hood-like criminal who has given $100 bills to homeless people and cooked dinner for hungry neighborhood kids, even mowing his mother-in-law' s grass and watering her roses.

Unlike Eric Rudolph, the convicted Olympics bomber who eluded a massive FBI dragnet in the western North Carolina mountains for five years, Gay's favorable reputation is heavily tied to his nonviolent demeanor.

"What he has done is definitely wrong, and he is a criminal, but I am still proud of him as a person," Ms. Tapola-Gay wrote in a letter to a Nashville TV station after his arrest in 2007.

Poor people, especially, are sympathetic to Gay's plight, chiefly because he uses his country smarts and Broadway-caliber talents to outwit "the man," says O'Brien, the songwriter. "He's kind of the wild and crazy guy meets 'Dumb and Dumber,' though it's not that he's dumb, maybe just foolish," he says. "I think the justice system wants us to believe that they can get everybody, so you kind of want him to see his family and escape somewhere and live happily ever after somehow. The only way to do that is to be an outlaw, and maybe it's still possible. I think it is."

Gay's exploits are headed for legend, set first to song and now to film. Indeed, after this latest escape, the Hollywood director Craig Brewer ("Hustle & Flow," "Black Snake Moan") will have to go to rewrite for his upcoming movie based on Gay's exploits.

Cheatham County Assistant District Attorney Bob Wilson isn't so awe-struck. "He's a little thief, a little con," says Mr. Wilson, who has an outstanding warrant for equipment theft ready to serve to Gay. "I'm just looking forward to seeing him."

In Pleasant View, Tenn., one of a handful of little towns and backcountry burgs where Gay grew up and still seems most comfortable, Police Chief Michael Douglas credits Gay with "being pretty good at what he does."

Pleasant View is where this tale really began. In 2006, Gay conned a Nashville towing company, convincing them to pick up a bulldozer at a local construction site. Over his career, Douglas says Gay stole millions of dollars worth of equipment, part of a fencing ring that would misappropriate heavy equipment, scratch out the VIN numbers, and paint them to look like new.

After being nabbed for stealing an RV in Alabama, Gay was being extradited to Tennessee to face the bulldozer charge when he escaped the first time, using a paper clip hidden in his mouth to unshackle himself from both handcuffs and leg irons.

During his 2007 run, he stole Gayle's tour bus not by hotwiring it, but by walking into the management company's office and asking for the keys. "He hasn't gotten through life killing people, but outwitting them," says Prof. Mihm.

Indeed, even Tennessee law enforcement officials view Gay's coolness and lock-picking skills with begrudging respect. Police, in fact, gave him the nickname "Little Houdini." Touched by Gay's attempt to see his mother. Coopertown, Tenn., police chief Dave Barrera made it known that Gay could see Annie one last time if he turned himself in, a reunion that never happened.

This week, Gay did what he has always done: Greet opportunity when it walks through the door. Perhaps aware that Capt. Thomas didn't know his reputation, Gay started working on his escape after Thomas stopped to eat at a Waffle House in Kennesaw. When Thomas returned, Gay asked to use the restroom. When the deputy opened the door, Gay, suddenly unshackled, bolted.

Though police have never known Gay to be violent, and Georgia media described him as "not dangerous," college officials locked down the Kennesaw State University campus on Tuesday, as unconfirmed eyewitness accounts described Gay walking through a dining hall as cool as a Sunday breeze.

Though there's no evidence that Gay has a gun, authorities have labeled him as "armed and dangerous."

"If a guy is wanting to escape as much as he is, we feel like he's going to try to do anything to get out," says Chief Douglas in Pleasant View.

Capt. Thomas, a 35-year-veteran, almost refused to come back to Tennessee until he caught up with Gay, says Coffee County Sheriff Steve Graves. In response to the escape, the sheriff's department has already mandated more intense background checks on prisoners lined up for transport.

"[Thomas] definitely wants to be the one who goes and picks [Gay] up when he gets caught," says Sheriff Graves. "But this time I'll send someone with him."