Ramblin’ Jack—not to be confused with Ramblin’ Jack Elliott, above—ran away from home to join the rodeo. David Briggs

“A tall tale doesn’t mean that the tale is a lie. It just means that it’s tall.” — Ramblin’ Jack 

Most people agree that Ramblin’ Jack, who was a student of Woody Guthrie, a self-appointed adoptive father of Bob Dylan, and has drawn the admiration of neon names like Paul McCartney, Tom Waits, Bruce Springsteen, Johnny Cash, Jack Kerouac and Slick Willy Clinton himself, has lived a unique life. The Grammy-winning cowboy has recorded 18 studio albums, 14 compilations and five collaborative albums. There is plenty of hot light on Jack’s exploits. But few know the real story. 

“I was supposed to be born in Miles City, Montana,” Jack said. “The stork was flying towards Miles City and he happened to be flying low over Billings. Will James, a hero of mine who would paint pictures to sell or trade for a whiskey bill, was out in front of the bar. He saw the stork flying with me—you know how they do, with the diaper in their beak, all wrapped up? 

“Will was amazed, and beckoned for the stork to come on down. It landed, walked into the bar with Will (he died from alcohol at age 50) and had a drink. He must have had three or four drinks, truthfully. When that bird finally realized he’s got this baby, he took off, really discombobulated, and I got delivered to Brooklyn by mistake.” 

It’s the only conceivable explanation for why an old cowboy like Jack was born to an upper-class family in Brooklyn. “It’s my story, and I’m sticking to it,” Jack said. 

For no reason other than a vague, though fond, memory of hanging out in a Montana bar while a long-necked wading bird got into a serious drinking contest with an alcoholic cattle-rustling painter, Jack started reading Will James’ books when he was 12 years old. In fact, he read all 23 of James’ books in one day, during a lunch break at school. 

He started with Cowboys North and South as he was peeling the foil off of his Jell-O (Jack ate his Jello-O first at every meal, a fact which, through a lengthy series of events, led to the creation of Elmer Fudd in March of 1940, though that’s a story for another day). By the time he got to his carrot sticks, Jack was halfway through The Three Mustangeers. When he opened his milk, he was turning the first page of The Dark Horse. He finished The American Cowboy with exactly one second before the bell rang. 

Jack knew he was destined to be a cowboy, and it was just his luck that the Madison Square Rodeo was coming to town. “My parents made the sad mistake of bringing me to that rodeo,” Jack said. “It had all the best cowboys in the country.” 

When he turned 15, Jack packed his belongings into a knapsack and set out to become a cowboy. “I got a job at a traveling rodeo, making two dollars a day grooming horses,” he said. “I brushed ‘em, fed ‘em, slept right there on the ground in a tent with 60 horses.” 

Despite the hard work—he put in a solid 23 hours each day, with one hour off for lunch—Jack was happy. “It was probably the only reputable rodeo east of the Mississippi River,” Jack said. In fact, it was the only rodeo east of the Big Muddy. There had been one other rodeo outside of Bangor, Maine, but a freak tornado had picked it up—cowboys, horses, bulls and all—before dropping it off a few miles from El Paso, Texas. 

Jack’s parents, who hadn’t heard from him in months, started circulating pictures of the runaway through the Bureau of Missing Persons. “I just completely forgot about [writing them],” he said. Jack’s parents were no rubes, and they sent flyers to every ranch and rodeo for which they could find an address, knowing that their son was of the cowboy persuasion. 

The jig was up once Jack’s boss, Col. Jim, found out he was a runaway and contacted the boy’s family. His mother and father drove up to the ranch, roped him, tied him and drove him back home. Jack bit through the ropes twice, but his parents had brought a few spare coils in case of just that eventuality. 

By then Jack had gotten to know a lot of the guys on the rodeo circuit. “One of the cowboys was just out of the army. He was a paratrooper, so he had fantastic leg muscles,” Jack said. “He used to tight-leg the bulls. A lot of riders ride just by balance, but he’d get a good grip on ‘em.” The cowboy, who went by Harry Tompkins, worked at a dude ranch in upstate New York.  Jack asked his parents if he could join him there.

Jack’s father, a surgeon who had delivered very nearly every baby born in Brooklyn between the years 1920 and 1940, acquiesced, and Jack spent summer vacations on the dude ranch. 

“I rode a steer for three jumps, and you can’t get hurt riding steers,” Jack said. “They’re little and not vicious. But that steer was the only cow-type animal I ever rode. I’m terrified of bulls. When I was in the arena, working for the rodeo, I always kept a hand on the fence.” 

Bulls weren’t the only part of cowboy culture that was hazardous to a growing boy’s health. “I hadn’t quite discovered the dangers of tobacco back then, when more cowboys smoked and chewed,” Jack said. “This gentleman, Mike Hastings, always had his cheek puffed out with apple chewing tobacco. It was very strong stuff; a solid plug wrapped in paper. You had to have real strong teeth to bite a chunk.” 

With the help of a chisel, sledgehammer and a half-stick of expired dynamite, Jack managed to break off a small piece. “I took a tiny little bite and got so dizzy I almost fell off my horse,” he said. “The spit hit my knee, dribbled down and off my stirrup in a solid stream of tobacco juice. It was pretty hard stuff. I gave it up.” 

When Jack was working for the rodeo, Marlboro cigarettes were not yet associated with cowboys. “I met one of the Marlboro cowboys, the first one who was very famous, the foreman of a ranch in Green River, Wyoming,” Jack said. “Darrell Winfield was his name, but he died of cancer. You see, Marlboro gave him all the cigarettes he could smoke, and he must have smoked like a steam engine. He was the first of three Marlboro men to die of cancer.” 

It’s a little-known fact that Bob Dylan smokes Marlboros. “I don’t think he advertises it,” Jack said. “If he did, half of America’s youth would be dead by now. He must be nuts. But then, most geniuses are nuts.” 

But Jack’s getting ahead of himself. When he was working at the rodeo, Jack met a rodeo clown named Brahmer Rogers—named after the breed of cow that is worshipped in India—while working at the rodeo. Brahmer recited cowboy poetry and sang, which piqued Jack’s interest. 

After his parents dragged him back home, Jack started learning to play the guitar, but the steep learning curve was frustrating. So, in exchange for seven silver dollars and seven years of his life, an old Gypsy woman gave Jack all the musical talent in the state (which is why no talented musicians were born in New York in 1946). He started busking for a living, and soon drew the attention of Woody Guthrie, the legendary musician who would shape his future.

Jack met Woody in 1950, and declared that he wanted to be Woody’s acolyte and ward. “I was fascinated by the way Woody sang without any fancy embellishments or histrionics like some of our pop singers,” Jack said. “He was totally real and natural and telling it like it is, not putting in a lot of false grunts and groans for the ladies in the balcony.” 

Woody, whose health was deteriorating from Huntington’s disease, accepted Jack’s offer and took him in as a pupil and friend. Jack spent nearly every day at the Guthrie home, studying his methods and style. He emulated Woody’s style so perfectly, reproducing every mannerism and nuance with natural confidence, that Woody once said, “Jack sounds more like me than I do.” (Though, when Jack started brushing his teeth and scrambling eggs just like Woody, he was told to knock it off.)

After touring together in Florida and California, Jack left Woody’s tutelage to explore the greater world on his own. Of course, leaving his mentor had been an accident. While fishing off the coast of Florida, Jack hooked the biggest, meanest lamprey eel in creation. Over 30 feet long and six feet wide, that eel dragged Jack off the pier and through the water and toward the horizon. By the time Jack could catch a breath, he was already speeding through international waters. By the time the sea monster finally got tired, he was only a few miles from the beach of Plymouth, England. 

Jack traveled around Europe, playing Woody Guthrie and cowboy songs, and even recorded some albums in London. There, Jack had a modest influence on the British music scene. “I bought my first guitar after seeing Jack perform,” Mick Jagger once said. 

“What was it Paul McCartney said?” Jack asked at a live concert in San Francisco in 1999. “He said he learned the San Francisco Bay Blues off of my early English recording, and I know he did, too, because he sang it with all the same mistakes that I did.” 

When Woody was on his last legs, in 1961, Jack came back to America to visit him in the hospital. There, he met another would-be pupil of Woody’s. “There was this kid, Bob Dylan, visiting Woody,” Jack said. “[Bob] said he had all six of my record albums recorded in England, somehow got a hold of them, and said he liked them.”

Jack became a father figure to Bob, whose father, Abram, had contracted polio when Bob was just six. Woody, Bob’s icon and hero, was too ill to teach any more students. But Jack, who by then had gleaned everything Woody had to teach, passed his knowledge on to the young folk singer. 

Though he still traveled, Jack was happy to be back in the U.S. of A. He even bought his first horse. “His name was Young Brigham. He was a Mormon,” Jack said. “He was very opinionated. He didn’t like hippies. I tried to turn him on to marijuana, but he didn’t like it.” 

Jack continued to record album after album. Sometimes, Jack would secretly record three or four records at once, in order to give himself a break whenever the public came howling for a new one. And, true to his name, Jack kept traveling the country, meeting a number of strange travelers.

“I used to know this guy from Washoe Lake. A Russian,” Jack said. “He was flying [his plane] in Oregon, and he had to pee real bad. So he landed in a farmer’s field, hit a bump and the plane did a flip upside down. He wasn’t hurt, but he quickly hitchhiked out of there, because he was afraid the farmer would be mad at him for breaking up his nice tilled field. [That Russian] made the most delicious pickles and borsht.”

After hanging out in Los Angeles for a while—“a godless town”—Jack decided he needed some religion. “I was a born-again Christian for a while,” he said. “Everyone in this church was so loving and friendly. I got baptized and became a member of the church for a little while there. I still have a prayer I say whenever I fly that mentions every important part of the airplane. I say it while taxiing, because it takes quite a few minutes to say, and helps dispel some of the boredom of going to take off. [It begins,] ‘God bless this plane, pilot and crew. God bless the wings and the fuselage too….’ So far it’s always worked for me.” 

After all his adventures, Jack decided that one lifetime wasn’t enough, so he decided to treat himself to a second time around. This month, Jack started aging backwards. “I was supposed to turn 80, but I couldn’t do it,” he said. “I was pretty tired of 79, and I didn’t want to be 80. It feels good, too, getting younger. In another 78 years I’ll be born. Back to the womb.”