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The Most Interesting Man in the World Has Nothing on the Guy Who Made Him Famous

Jonathan Goldsmith, 78, is lounging on a stack of throw pillows, on a bench overlooking a hillside terraced with grapevines, set among the lush green hills of L.A.’s Topanga Canyon, smoking a fat Cuban cigar. A pair of hawks circle overhead, riding the updrafts; in the distance, the blue sky meets the blue Pacific Ocean. The sun warms his face, deeply tanned with bronzer by a makeup artist, framed within the razor-sculpted lines of his familiar salt-and-pepper beard, which has been darkened here and there with a product called Liquid Hair. A small patch of lightly forested belly lies exposed by an errant flap of his untucked shirttail. The little hillock of pale skin rises and falls, rises and falls, measuring his even breaths.

The lookout spot is part of an estate that’s been rented by an ad agency for a series of commercials about Luma, a new kind of wireless router system that provides network security for the home. Goldsmith is here to play himself — wise and wisecracking, the ultimate help-desk authority. The web is a cesspool of digital sickness, and you’re swimming in nothing but goggles. A catered lunch for the 50-person crew has just concluded. With another half hour to go before his next shot, Goldsmith has climbed the 50 or so steep stone steps that wind up the hill. Because he’s wearing a brand-new pair of blue suede shoes — an inside joke among the wardrobers? — the soles are unscuffed and slippery. Faltering a bit along the trail, he rested his hand upon his son’s forearm for balance.

Since 2006, when he first showed up in regional commercials as the brand spokesman for Dos Equis, a formerly obscure Mexican brewer owned by Heineken, Goldsmith has been known across the planet as the Most Interesting Man in the World. An ageless, debonair adventurer with a suave Latin delivery and big brass balls who has lived life to the fullest, his only regret was not knowing what regret feels like. A cross between James Bond and Don Juan (with a dash of Don Quixote), he became internationally known for his aristocratic bearing, his incredible feats of daring, his kindness to children, his addictive charm.

Over time, a series of clever ads painted a pointillist portrait: His shirts never wrinkled. He could parallel-park a train. His mother had a tattoo that says S-O-N. One time he went to a psychic — to warn her. Sharks had a week dedicated to him. His business card read, “I’ll Call You.” He was allowed to discuss Fight Club. His beard alone had experienced more than a lesser man’s entire body. He lived vicariously through himself.

He was… the Most Interesting Man in the World.

Until last year, anyway.

“It was the company’s decision,” Goldsmith says. He shrugs his shoulders, blows a gray cloud of smoke into the air. His accent is classic New York City, where he was born. “They decided to go in another direction. They thought I was too old. They wanted to bring in a younger guy. They’d made a deal to sponsor the college football playoffs, I guess. They thought the demographics would be more favorable to connect with their audience.”

For its part, Dos Equis played the exit to the hilt. They used the hashtag #adiosamigo and distributed life-size cardboard cutouts to grocery stores and bars around the world so fans could take selfies. They ran a sweepstakes, giving customers the chance to win some of the Most Interesting Man in the World’s possessions, including his mariachi suit. His concluding commercial appearance, which aired in March 2016, was reminiscent of a state funeral, attended by fictional representatives from across the fictional globe.

After shaking hands all around and giving a set of keys to a Buddhist monk, the brand representative who saw Dos Equis sales rise more than 34 percent during his stewardship — taking the product from an unknown regional brand to one of America’s most popular — boarded a rocket for a one-way trip to Mars.

He was replaced by a 41-year-old Frenchman. Initial response on the company’s website wasn’t good, as reported by TMZ:

Susan Brahm Czysz: I so miss the original guy. He was 10 times better. They really messed up those commercials.

Shelia Duncan: There is only 1 most interesting man in the world. And this guy is not it!!! Bring back the real Most Interesting Man… Please.

Saralea: They did that switch all wrong there. They should have said the most interesting man in the world is so interesting that he has a son! The most interesting DUDE in the world. Duhhh… can’t be on board with this NEW interesting man. I don’t buy it.

According to a poll by the research firm YouGov BrandIndex, the numbers agreed. Early numbers showed that brand consideration in the target age group dropped by more than half. “Millennials aren’t finding the new Most Interesting Man in the World all that interesting,” wrote Advertising Age.

“Of course, it turned out they were wrong,” says the former Most Interesting Man in the World, tilting his head imperceptibly and raising an eyebrow. You can almost hear the strains of Flamenco guitar.

“You can’t just act interesting, my friend. You have to be interesting.”

At the time he landed the Dos Equis gig, Goldsmith had been knocking around New York and Hollywood for nearly half a century, scoring small parts in some 350 theater, TV and film productions by his count. His specialty as an actor, he likes to say, was “falling off horses and getting killed in a variety of ways.”

During the course of his career, he worked with Burt Lancaster and John Wayne, Shelley Winters and Joan Fontaine; caroused with playwrights Tennessee Williams and Arthur Miller; crossed egos with Dustin Hoffman; painted houses with Nicholas Colasanto (the guy who played Coach on Cheers); slept with a bevy of starlets, including Tina Louise, who played the hot marooned actress on Gilligan’s Island, and “six vegetarians, nine Buddhists, 18 nurses, six teachers, countless receptionists and one runner-up to Miss Florida.”

Later, he started a production company with his great friend, the Argentine actor and bon vivant Fernando Lamas, who was married to Hollywood’s favorite aquatic nymph, Esther Williams. At age 67, facing a roomful of much younger Latino actors who were auditioning to become the face of a new Mexican beer, Goldsmith would channel the accent and mannerisms of the departed Lamas, whose ashes Goldsmith had some years earlier sprinkled into the ocean from his sailboat. (Billy Crystal’s archetypal playboy character, Fernando — “You look maaaaarvelous” — was another borrow from Lamas.)

The friend, lover and colleague of stars — but never star himself — Goldsmith had long ago given up his Hollywood hopes by 2006, when he auditioned for the part of the Most Interesting Man in the World. At the time, he says, he was a desperate man, broke and broken, living in the bed of his 1965 Ford Diesel pickup truck in a cold-shower campground in Malibu.

As he tells me over the course of two days and writes in his forthcoming autobiography, Stay Interesting, Goldsmith’s life story — to the extent it can be verified — seems every bit worthy of the persona he would later wear in public, albeit without the accent.

Goldsmith was born in 1939 in New York City. His mother was Greta Roth, one of Harry Conover’s Cover Girls. In the years following World War II, Conover was known for having the first ultra-elite modeling agency; the term “cover girl” was derived from Conover’s early concepts. Looking back, Goldsmith says his mother might have lacked a certain innate ability to nurture. Case in point: When he was six months old, he says, she left him in a grocery store in Riverdale. (“Though she did remember to take her groceries,” he adds.)

Roth had tragically lost her own mother when she was young, leaving her father to raise her and an older brother, which he did mostly by farming out the children to different relatives. Despite a “debilitating deformity of his legs that made it difficult to walk,” Goldsmith writes, his grandfather was “a radical eccentric, an intellectual and a drifter” who wandered the country for a time in a camper, lived on a pirate boat off Costa Rica, and helped start Muscle Beach. Emotionally, his mother and her brother were left to fend for each other.

Goldsmith’s father was Milton Goldsmith. He too was an eclectic sort. Briefly a semi-pro basketball player, he later trained boxers. According to family lore, he’d beaten the New York City quarter-mile champion in a foot race while wearing street shoes. Later Milton settled down and became a P.E. teacher. A devoted outdoorsman, he taught his son to fly fish and shoot a Winchester .22 rifle. Jonathan’s uncle once said to him: “Your father is the most successful man I know because he has no ambition at all.”

After a short marriage, Goldsmith’s mother divorced Milton and married Jerome S. Lippe, the owner of Leipzig and Lippe, which manufactured housewares, baskets, barbecues and other home products. After a lavish ceremony in Havana, they took an apartment in a Park Avenue hotel. There were servants and silver trays and a Haitian maid Goldsmith recalls as One-Eyed Betty, who believed in voodoo and went fishing with him in the reservoir. Lippe adopted the boy, and his last name was changed. In fact, even early in his acting career, Goldsmith went by the name Jonathan Lippe.

At age 5, Goldsmith was packed off for a place he remembers as Mrs. Hunt’s Boarding School in Cedarhurst, Long Island. His mother told the headmistress he was a “difficult child at home — a naughty, unloving, unmanageable boy.” When he saw “the taillights of her taxi disappear,” he writes in Stay Interesting, he ran as fast as he could, trying to catch her. Unsuccessful, he “hid under the yellow flowers of a forsythia bush,” but was soon found and remanded.

In the coming years, Goldsmith would frequently go AWOL from the school and take a series of trains to his father’s humble apartment in Harlem. Among his favorite memories of childhood were mornings when he’d “wake up on the couch under the sheets he kept for me in the closet,” sleeping in one of his oversized T-shirts. “I’ve had trouble sleeping all my life, but never in those shirts. It was like a shield, and my father was my protector.”

After a series of misadventures, disciplinary problems and matriculations to different boarding schools, Goldsmith ended up back in public high school in Westchester County, where he played on the basketball team and met a friend (the only other Jew in the rural school) named Anthony Hatzenberg, who wore his hair slicked back and went by the nickname of Tony Mambo. It was Tony who took him into New York City and introduced him to his first hooker, who was “pretty enough,” and wearing a long, oversized T-shirt. “Edie Matthews, bless her, made me a man,” he writes in his book.

Always eager to earn money since it represented independence to him, Goldsmith worked throughout high school at a variety of jobs. He delivered newspapers, was a stock boy at a liquor store and worked on a Christmas tree farm near the Sing Sing Prison. “Whenever they would execute somebody, the lights on our Christmas trees would grow dim,” he recalls. He also worked at a number of Catskills resorts as a busboy, salad man and waiter. One memorable afternoon he stuffed 2,000 prunes with peanut butter. He was fired at every stop for one reason or another — side hustles, charging extra food to guests (which he’d eat himself), placing bets at Saratoga racetrack for guests.

After two years at a Boston junior college, where he “majored in gin rummy and minored in dog handicapping” at the Wonderland Greyhound Park, Goldsmith returned to New York. Since he was small, Goldsmith says, he’d suffered from anxiety and night terrors; for his whole life, he says, he felt unwanted and insecure. He saw his first psychiatrist at age 5 or 6 and continued going to therapists on and off throughout his childhood, mostly to please the adults. After college, concerned about his son’s future, his father sent him to meet a friend of his — Fredric Wertham, a well-known German-American psychiatrist and author most remembered for his crusade against violent imagery in mass media and comic books. This time, something clicked.

At the conclusion of their session, Goldsmith remembers vividly, Wertham told him: “Your mother, I feel sorry for her.” For the first time in his life, Goldsmith says, he felt like someone truly understood him. Then the doctor told him he was going to arrange an introduction to Broadway director Philip Deacon, who was teaching acting classes on the Lower East Side.

Attending his first class, Goldsmith was asked to do an improv — a man carrying a heavy suitcase full of cash across a desert. “When I had finished, I looked around,” Goldsmith recalls. “The entire class was standing and clapping. I had done something extraordinary, and it felt so natural. The applause alone was intoxicating. I knew from that moment my life would never be the same. I’d found my calling.”

Goldsmith spent the next several years taking more acting classes, living in cold-water walk-ups and playing small roles off Broadway and at regional theaters around the country. In 1961, he got his first big break in an early run of Natural Affection by William Inge (who would later invite him to his house in L.A. and propose taking a shower together). The play was directed by Harold Clurman, founder of the Group Theater in New York and the husband of legendary acting coach Stella Adler. The female lead in the play was Shelley Winters. After Goldsmith appeared again with Winters in a 1962 Broadway production of Tennessee Williams’ Night of the Iguana, Winters urged him to come to Hollywood to meet her agent.

Goldsmith can’t quite remember the exact year, but sometime around 1963 or 1964, he bought a used VW Bug and drove across the country to L.A. He crashed with a friend from the Neighborhood Playhouse in New York, Walter Koenig, who would later become well-known for playing Chekov in Star Trek. On his first night in Hollywood, he saw The Doors at the Whisky A Go Go.

Over the next 30 years, Goldsmith would pursue the rocky life known to generations of Hollywood’s Almost Famous — living in odd places (an abandoned frog farm), doing odd jobs (driving a garbage truck) and having odd experiences (locked out of a woman’s house naked, his car broke down on the drive home; the responding officers thought he was insane). In time, he began to land roles, most of them small parts. He did a lot of Westerns: Gunsmoke, Bonanza, High Chaparral, The Virginian and Hang ‘Em High. But there were also roles on The Doctors, My Three Sons, Dynasty, Charlie’s Angels and Knight Rider.

Regardless: “Usually I was cast as a guy who was about to be killed,” he says.

He was pushed off roofs in T.J. Hooker, Dallas and Streets of San Francisco (in another episode he drowned in a bathtub). In other shows, he was mowed down by a machine gun, electrocuted, blown up by dynamite, run over by a car, pushed off a boat into a mucky swamp and hanged from a gallows.

In the Shootist, the last film starring John Wayne, Goldsmith was killed by the Duke himself, shot in the forehead. The scene took nine takes. Wayne’s gun had blanks, but off-camera, there was a prop man with an air gun who fired pellets filled with fake blood at Goldsmith’s forehead, “leaving a nasty welt.”

In time, Goldsmith says, he just couldn’t take it anymore. Facing 60 and still struggling, married, trying to raise and educate a family, he decided to end his acting career. “There was no doubt I worked hard to make it,” he says. “I put in my best efforts. I was friends with a lot of stars. I knew plenty of people around town. I owned a production company with Fernando. But I just couldn’t seem to get over the last hump. Finally, I decided, Screw it. I’m done.

Instead, Goldsmith started a company that marketed waterless car-wash products. At one point, he says, he employed more than 100 people and “was netting more than $150 million a year in profits,” according to his book. He was married with children, lived in a custom-built house on 120 acres in the High Sierras and owned a 60-foot sailboat. But after nearly a decade, for reasons he declines to discuss, the company disintegrated, Goldsmith says. His marriage soon followed.

By 2006, when the call came for the Dos Equis audition, Goldsmith was at his wits’ end. “I had no income and lots of bills — attorneys, mortgage and more. I was looking at bankruptcy,” he says. His sailboat, the one from which he’d sprinkled the ashes of his old friend Fernando, was on the auction block. With nowhere else to turn, he decided to give acting another shot.

After shaving in the sideview mirror of his truck, Goldsmith drove to the audition in Hollywood. The line of actors disappeared around the block, all of them younger and Latino. According to his agent, the Dos Equis people were looking for “a Hemingway kind of guy.” For the audition, all the candidates would be asked to do an improv, ending with the line, “…And that’s how I came to arm-wrestle Fidel Castro.”

As he had in that first acting class so many decades ago on the Lower East Side, Goldsmith killed it. There was applause in the audition room. They called his agent that afternoon with the news.

Over the next decade, the Most Interesting Man in the World became part of the zeitgeist, a universally beloved figure, the ultimate personification of cool. Michael Jordan asked for a selfie with him. Leonardo DiCaprio crossed a restaurant to shake his hand. President Barack Obama invited him as the guest of honor to his exclusive 50th birthday weekend at Camp David with 10 of his closest friends.

Pete Souza/White House

And then, in March of 2016, it was over.

“Honestly, it was a little bit of a shock,” Goldsmith says. “But it was a hell of a run.”

Back inside the rented estate in Topanga Canyon, at the commercial shoot for Luma, Goldsmith is in a dressing room on the first floor, being readied for his next scene. As the makeup artist touches up his face, the sound guy snakes a microphone cord around his torso. The wardrobe woman buttons a crisply ironed white shirt.

Goldsmith continues talking as the crew fusses, accustomed to the routine. He waves his unlit cigar for punctuation. He is warm and unguarded, accommodating even though I can tell it’s a bit of a burden. Approaching his ninth decade, he is still vibrant. Later, though, between takes, I’ll catch him in the chair fast asleep. But for the moment, he’s feeling chatty. I’ve asked him about his Dos Equis commercial highlights — he’s reminiscing about his various animal co-stars.

“They were fun, but they were dangerous,” he says, sounding a little more like Woody Allen than Fernando Lamas. “Imagine being 15 yards away from a wild rhinoceros. Or semi-wild, anyway. When they told me his name was Spike it didn’t make me feel any better. The only thing between me and him was this kid with a little circus whip.”

“Another time I worked with this puma,” he continues. “He hated me. He had these big green eyes, and he just hissed at me and spit at me. But the one that frightened me the most was the barn owl. He would fly down and land on a gauntlet I had. He had these huge claws, and I could feel them clamping down. I worried that even if I moved wrong…”

Today, Goldsmith lives with his second wife, Barbara, the agent who got him the Dos Equis audition, on a rural property with views of the mountains near Manchester, Vermont, where he hunts, fishes and chops his own wood, and where he still receives hundreds of letters from fans every month. When he’s not there, he’s either making public appearances or spending time visiting his five children (ages 32 to 47), 11 grandchildren and 7 great-grandchildren.

Last week, he introduced Jay Leno at a charity benefit. Next week, he’s going to a ceremony on an Native American Indian reservation. This summer, he’ll be hosting KAABOO, the high-end oldster music festival in Del Mar, California. He’s spoken at Harvard twice. He’s also a spokesman for the Make-A-Wish Foundation in Vermont and works closely with Hunger Free Vermont and other local charities. “Vermont is a very poor state,” he says. “One out of five kids goes to bed hungry. And we have a drug problem.” He’s active in politics as well, which is how he met Obama in the first place, during the former president’s race for a second term.

While playing the Most Interesting Man in the World has made Goldsmith wealthy, beloved and iconic, the effect goes much deeper. “When I was younger, I always felt slightly uncomfortable in a crowd,” he says. “I never liked the party atmosphere, I never had the ability to laugh freely and wholeheartedly. I was always conscious of guarding myself, conscious of real or imagined insecurities. It was always like I was viewing life from a distance.

“So for me, playing him was amazingly liberating. He had facilities and ease that I didn’t have. I enjoyed being that character. The reactions of people were astounding. Political figures. Sports figures. Celebrities. They all wanted to meet me. After I first met Obama I was driving home with my wife, and I said, ‘This guy actually seems to like me. He’s interested in me. How can that be?’”

It’s like that thing they teach for self-improvement, I suggest. Becoming the person you project.

He looks at me earnestly. “I always knew I was a good person,” he says, “but I never felt like I was a successful person. I do now. I feel a confidence that eluded me most of my life. There’s a lot of wonderfully talented people in the world. Beautiful actresses, handsome actors, stars. But there’s only one Most Interesting Man in the World.”