JENN AND BILLY met in the summer of 2002, after Billy had finished his freshman year atVirginia Commonwealth University and returned home to lifeguard on Virginia Beach. Onemorning, he arrived at his stand to discover that the Luck of the Bonehead had struck again. Hisnew partner was a Corona commercial come to life, a beauty who earned top marks in all theBonehead scoring categories: she was a surfer, a secret bookworm, and a hard-core partyer whoseancient Mitsubishi had a life-size silhouette of gonzo writer Hunter S. Thompson aiming a .44Magnum stenciled on the hood.

But almost instantly, Jenn began to bug him. She fixated on Billy’s University of North Carolinabaseball cap and wouldn’t let up. “Dude!” Jenn said. “I need that lid!” She’d gone to UNC for ayear before dropping out and moving to San Francisco to write poetry, so if there was any karmicjustice on this beach, then she should be sporting the Tar Heels gear, not some pretty-boy surferlike him who only wore it to keep the pretty-boy bangs out of his eyes….

“Fine!” Billy erupted. “It’s yours.”

“Sweet!”

“If,” Billy continued, “you run down the beach, bare-ass.”

Jenn scoffed. “Dude, you are so on. Right after work.”

Billy shook his head. “Nope. Right now.”

Moments later, hoots and cheers rocked the boardwalk as Jenn burst out of a porta-potty, herlifeguard suit crumpled on the ground behind her. Yeah, baby! She made it to the next stand ablock away, turned around, and came charging back toward the throngs of moms and kids she wassupposed to be protecting from, among other things, full-frontal nudity by college dropouts goin’

wild. Amazingly, Jenn didn’t get canned (that came later, for shorting out the engine of herlifeguard captain’s truck by sticking a live crab under the hood).

During quieter moments, Jenn and Billy talked big waves and books. Jenn revered the Beat poetsso much, she was planning to study creative writing at the Jack Kerouac School of DisembodiedPoetics if she ever dropped back into college and got a degree first. Then she picked up LanceArmstrong’s It’s Not About the Bike and fell in love with a new kind of warrior poet.

Lance wasn’t just some brute on a bike, she realized; he was a philosopher, a latter-day Beat, aDharma Bum sailing the asphalt seas in search of inspiration and Pure Experience. She’d knownArmstrong had bounced back from cancer, but she had no idea just how close to the grave he’dactually been. By the time Armstrong had gone under the knife, tumors were spreading throughouthis brain, lungs, and testicles. After chemotherapy, he was too weak to walk but had to make anurgent decision: should he cash in an insurance policy worth $1.5 million, or turn it down and tryrebuilding himself into an endurance athlete? Take the payout, and he’d be set for life. Turn itdown and relapse, and he’s dead meat; he’d have no money, no health insurance, no chance ofseeing age thirty.

“Fuck surfing,” Billy blurted. Living on the edge wasn’t about danger, he realized. It was aboutcuriosity; audacious curiosity, like the kind Lance had when he was chalked off for good and stilldecided to see if he could build a wasted body into a world-beater. The way Kerouac did, when heset off on the road and then wrote about it in a mad, carefree burst he never thought would see thelight of print. Looking at it that way, Jenn and Billy could trace a direct line of descent from aBeatnik writer to a champion cyclist to a pair of Pabst Blue Ribbon-chugging Virginia Beachlifeguards. They were expected to accomplish nothing, so they could try anything. Audacitybeckoned.

“You ever heard of the Mountain Masochist?” Billy asked Jenn.

“Nope. Who’s he?”

“It’s a race, you crackhead. Fifty miles in the mountains.”

Neither of them had even run a marathon before. They’d been beach kids all their lives, so they’dbarely seen mountains, let alone run them. They wouldn’t even be able to train properly; the tallestthing around Virginia Beach was a sand dune. Fifty mountain miles was waaaay over their heads.

“Dude, that’s totally it,” Jenn said. “I’m in.”

They needed some serious help, so Jenn looked where she always did when she needed guidance.

And as usual, her favorite chainsmoking alcoholics came through in the clutch. First, she and Billydug into The Dharma Bums and began memorizing Jack Kerouac’s description of hiking theCascadia mountains.

“Try the meditation of the trail, just walk along looking at the trail at your feet and don’t lookabout and just fall into a trance as the ground zips by,” Kerouac wrote. “Trails are like that: you’refloating along in a Shakespearean Arden paradise and expect to see nymphs and fluteboys, thensuddenly you’re struggling in a hot broiling sun of hell in dust and nettles and poison oak… justlike life.”

“Our whole approach to trail-running came from Dharma Bums,” Billy told me later. As forinspiration, that’s where Charles Bukowski stepped up: “If you’re going to try, go all the way,” theoriginal Barfly wrote. “There is no other feeling like that. / you will be alone with the gods / andthe nights will flame with fire…. you will ride life straight to / perfect laughter, it’s / the only goodfight there is.”

Soon after, surf fishermen noticed weird goings-on each evening as the sun set on the Atlantic.

Chants would echo across the dunes— “Visionnnnns! O-O-O-O-O-mens!

HallucinAAAAAtions!”—followed by the appearance of some kind of loping, howling, four-legged man-beast. As it got closer, they could see it was actually two people, running shoulder-toshoulder.

One was a slim young woman with a “Gay Pride” bandanna on her head and a vampirebat tattooed on her arm, while the other, as best they could make out, seemed to be a welterweightwerewolf under a rising moon.

Before setting out for their sunset runs, Jenn and Billy would snap a tape of Allen Ginsbergreading “Howl” into their Walkman. When running stopped being as fun as surfing, they hadagreed, they’d quit. So to get that same surging glide, that same feeling of being lifted up andswept along, they ran to the rhythm of Beat poetry.

“Miracles! Ecstasies! Gone down the American river!” they’d shout, padding along the water’sedge.

“New loves! Mad generation! Down on the rocks of Time!”

At the Old Dominion 100 a few months later, aid-station volunteers at the halfway mark heardscreams echoing through the woods. Moments later, a girl in pigtails burst from the trees. Sheflipped up in a handstand, jumped back to her feet, and began shadowboxing.

“This all you got, Old Dominion?” she shouted, throwing punches in the air. As the sole memberof Jenn’s support crew, Billy was waiting with her favorite midrace meal: Mountain Dew and acheese pizza. Jenn stopped bobbing and weaving and tore into a slice.

The aid-station volunteers stared in disbelief. “Hon,” one of them warned her. “You’d better take iteasy. Hundreds aren’t halfway done till you hit the last twenty miles.”

“Okay,” Jenn said. Then she wiped her greasy mouth on her sports bra, burped up some Dew, andbounded off.

“You’ve got to get her to slow down,” one of the aid-station volunteers told Billy. “She’s goingthree hours faster than the course record.” Tackling one hundred miles i............