Written By: Ben Cosgrove

From Jesse James and Butch Cassidy to Scarface and Tony Soprano, outlaws have held an ambiguous place in America’s popular imagination: we fear and loathe the gangster’s appetite for violence; we envy and covet his radical freedom. In early 1965, LIFE photographer Bill Ray and writer Joe Bride spent several weeks with a gang that, to this day, serves as a living, brawling embodiment of our ambivalent relationship with the rebel: Hells Angels.

Here, along with a gallery of remarkable photographs that were shot for LIFE but never ran in the magazine, Ray and Bride recall their days and nights spent with Buzzard, Hambone, Big D and other Angels (as well as their equally tough “old ladies”) at a time when the roar of Harleys and the sight of long-haired bikers was still new and for the average, law-abiding citizen almost unfathomable. The day-to-day existence of these leather-clad hellions was as foreign to most of LIFE magazine’s millions of readers as the lives of, say, Borneo’s headhunters, or nomads of the Gobi Desert.

“This was a new breed of rebel,” Ray told LIFE.com, recalling his time with the Angels. “They didn’t have jobs. They absolutely despised everything that most Americans value and strive for stability, security. They rode their bikes, hung out in bars for days at a time, fought with anyone who messed with them. They were self-contained, with their own set of rules, their own code of behavior. It was extraordinary to be around.”

Ray spent some of the time with the Angels on a ride from San Bernardino (about 40 miles east of Los Angeles) to Bakersfield, Calif., for a major motorcycle rally. The Berdoo-Bakersfield run is a trip of only about 130 miles but in 1965, it would offer enough moments (both placid and violent) for Ray to paint a rare, revelatory portrait of the world’s most legendary motorcycle club in its early days. The way in which the story came about, meanwhile, was as dramatic and unexpected as Bill Ray’s pictures.

“I’d done a story on Big Daddy Roth,” writer Joe Bride recalled, “a genuine L.A. phenomenon and legend in the Southern California car culture. He had a lucrative business designing hot rod-themed decals and cartoon figures. While I was wrapping up the story with Big Daddy, the Angels were in the news. They were accused of terrorizing a small central California town and being major growers and distributors of pot. Big Daddy said he knew a lot of Angels, did business with them and that they were more lost nomads than real criminals. After meeting them, by the way, my take on them was a little bit closer to the prevailing opinion than to Big Daddy’s. . . .”

“I told Big Daddy Roth I’d like to meet the Angels, talk to them about doing a story,” Bride said. “It would be a chance for them to get some recognition, and explain why they did what they did. Not long after the story on Big Daddy ran, in late 1964, Roth called and said, ‘They’ll meet you with conditions.'” Bride met two Angels at Big Daddy’s store. They blindfolded him, put him in a car and drove into the mountains. At a bar “with what looked like 100 bikes parked outside,” no longer blindfolded, Bride met a stocky, long-haired Angel who asked if he shot pool. They played some nine-ball, and Bride beat the guy two out of three games. Bride then negotiated, there in the bar, a relationship where the Hells Angels agreed to allow him and Bill Ray to shadow them. Bride sat back, had a few beers, and then they drove him back to L.A. Not long after that, Ray and Bride began reporting the story.

Ray and Bride spent more than a month with the Angels in the spring of ’65, “mostly on weekends,” Ray remembers, “but the Bakersfield run was around the clock, three days and nights. In Bakersfield, I slept on the floor of the Blackboard Cafe the bar that the Angels basically lived in while they were there.”

“I got along with the Angels,” Ray says today. “I got to like some of them very much, and I think they liked me. I accepted them as they were, and they accepted me. You know, by their standards, I looked pretty funny.”

Ray vividly remembers the moment he truly felt accepted, or as accepted as he was ever going to be, by the Angels. In a confrontation reminiscent of a famous scene in Hunter S. Thompson’s classic 1966 book, Hell’s Angels, when Thompson was almost stomped to death by bikers, Ray says that “he got in a bit of trouble one day, in a bar. Some bikers guys who weren’t Angels saw me taking pictures. They didn’t like it, but they didn’t realize that I was a sort of mascot of the real tough guys. I’d been shooting the Angels for maybe a week at this point. I was about to be attacked by one of these guys when a Hells Angel standing next to me made it clear that if a hair on my head was touched, the other guy was a dead man. From that point on, I felt . . . well, not safe, because I never felt safe with those guys, but as if I’d passed a test, somehow.”

Ray stresses that while the Angels he spent time with smoked pot, and he once saw them “beat the holy hell” out of some other bikers behind a bar, he “never saw these guys involved in anything deeply illegal. Then again, they always had plenty of money for gas and beer. They lived on their bikes that is, when they weren’t hanging out in bars. Their money had to come from somewhere, but none of them ever worked.”

The FBI has contended that the Angels and other motorcycle gangs are involved in extortion, drug dealing, trafficking stolen goods and other criminal activities.

“There’s a romance to the idea of the biker on the open road,” Ray says. “It’s similar to the romance that people attach to cowboys and the West which, of course, is totally out of proportion to the reality of riding fences and punching cows. But there’s something impressive about these Harley-Davidsons and bikers heading down the highway. You see the myth played out in movies, like Easy Rider, which came out a few years after I photographed the Angels. You know, the trail never ends for the cowboy, and the open road never ends for the Angels. They just ride. Where they’re going hardly matters. It’s not an easy life, but it’s what they choose. It’s theirs. And everyone else can get out of the way or go to hell.”

—gallery by Liz Ronk

Hells Angels, California, 1965. Bill Ray Life Pictures/Getty Images

Hells Angels, California, 1965. Bill Ray; Life Pictures/Getty Images

Big D, a member of the San Bernardino, a.k.a, “Berdoo” Hells Angels, during a ride from San Bernardino to Bakersfield, California, 1965. Bill Ray; Life Pictures/Getty Images

Inside the Hells Angels’ San Bernardino clubhouse, 1965. Bill Ray— Life Pictures/Getty Images

“Little Jim” drinks beer from a waste basket at the Angels’ clubhouse in San Bernardino, 1965. Bill Ray; Life Pictures/Getty Images

Hells Angels’ “old ladies,” California, 1965. Bill Ray; Life Pictures/Getty Images

Two “Berdoo” Hells Angels clown for Bill Ray behind a bar during a stop on their run from San Bernardino to Bakersfield, 1965. Bill Ray; Life Pictures/Getty Images

Hells Angel “Hambone” posed during a ride from San Bernardino to Bakersfield, Calif., 1965. Bill Ray; Life Pictures/Getty Images

Hells Angels and locals outside the Blackboard Cafe in Bakersfield, Calif., 1965. Bill Ray— Life Pictures/Getty Images

Hells Angels, their “old ladies” and hangers-on outside the Blackboard in Bakersfield, California, 1965. Bill Ray; Life Pictures/Getty Images

Hells Angels cruise north from San Bernardino to Bakersfield, 1965. Bill Ray; Life Pictures/Getty Images

A man in Bakersfield, Calif., cast what appeared to be an appraising eye over the Hells Angels’ Harley-Davidsons, 1965. Bill Ray; Life Pictures/Getty Images

Hells Angels Bill Ray; Life Pictures/Getty Images

Hells Angels Bill Ray; Life Pictures/Getty Images

Sonny, the leader of the San Bernardino Hells Angels, needed stitches in his head after crashing his bike, California, 1965. Bill Ray; Life Pictures/Getty Images

Women—including one with a bandaged nose—in a bar while male bikers gathered in a separate room, California, 1965. Bill Ray; Life Pictures/Getty Images

A sheriff’s officer kept an eye on the proceedings outside a bar that the Hells Angels had made their headquarters-away-from-home during their San Bernardino-to-Bakersfield run, 1965. Bill Ray; Life Pictures/Getty Images

Two women who were riding with the Hells Angels at a bar in 1965. “This is one of my favorites from the whole shoot,” Bill Ray says. “There’s something kind of sad and at the same time defiant about the atmosphere.” Bill Ray; Life Pictures/Getty Images

Hells Angels Bill Ray; Life Pictures/Getty Images

Outside the Blackboard Cafe at night, Bakersfield, Calif., 1965. Bill Ray; Life Pictures/Getty Images

Hells Angels Bill Ray; Life Pictures/Getty Images

A teenager seems drawn by the Angels and their machines, California, 1965. Bill Ray; Life Pictures/Getty Images

Two “reputable” motorcyclists photographing the Hells Angels, 1965. Bill Ray; Life Pictures/Getty Images

During their ’65 run to Bakersfield, the Angels pushed their way into a motorcycle hillclimb, in which bikers race up an often insanely steep incline. The Angels wanted to take part; organizers said no (but finally relented). Bill Ray; Life Pictures/Getty Images

A biker named Roseberry sported a “one percenter” patch—a badge of honor for the Angels and other motorcycle clubs whose members revel in and celebrate their outlaw status, 1965. Bill Ray; Life Pictures/Getty Images

A biker named Roseberry getting fingerprinted, 1965. Bill Ray; Life Pictures/Getty Images

An Angel getting frisked. Bill Ray; Life Pictures/Getty Images

A Hells Angel—with his “old lady” holding on tight—pulled a wheelie in downtown Bakersfield, Calif., 1965. Bill Ray; Life Pictures/Getty Images

Bikers (including Sonny, left, with a bandaged head) and their “old ladies,” California, 1965. Bill Ray; Life Pictures/Getty Images

Hells Angels Bill Ray; Life Pictures/Getty Images

“Buzzard” and an “old lady,” California, 1965. Bill Ray; Life Pictures/Getty Images

A Hells Angel salute, 1965. Bill Ray; Life Pictures/Getty Images