How Sir Paul McCartney Endured Prison and Other Hardships

Bradley Calvin
8 min readAug 3, 2019

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Sir Paul McCartney on tour in 2010 (Photo: oliver.gill)

In 1980, a decade after the collapse of the Beatles, Sir Paul McCartney arrived at Tokyo’s Narita International Airport where he was met first by screaming fans and TV cameras, and then handcuffs.

Perhaps the most adored and famous human on earth during Beatlemania’s zenith in the mid-sixties, Paul headed for Japan with his family over a decade later, this time as the frontman and leader of his own band.

Paul McCartney and Wings, a concert-attraction juggernaut, were to embark on an eleven-date world-tour beginning in Tokyo’s Budokan Hall, “where the Beatles had appeared in 1966 during the chaotic Far East tour that helped finally sicken them of live performance,” biographer Philip Norman writes in Paul McCartney: The Life.

Norman, with Paul’s tacit approval and access to Paul himself and those close to him, tells the story of this troublesome episode in Paul’s usually cushy life. During the “search of Paul’s luggage, the surgical-gloved customs officer lifted up a jacket to reveal a transparent plastic bag containing a large wedge of what was clearly marijuana.”

So, instead of progressing from private jet to presidential suite and later to the stage, he found himself spending the night in a holding cell, unable to sleep for fear “of being raped.”

Much different than modern times, or Europe or America back then, where he would receive bail, “Japan had no such system; pending a further investigation of the evidence against him, he would be held in custody.”

Potentially facing seven years’ imprisonment with hard labor, owing to Japan’s outdated and harsh anti-drug laws (Paul had only 7.7 ounces of weed), he was transferred to “central Tokyo’s grim nineteenth-century Kosuge Prison… in company with some of Japan’s most hardened criminals, and to be treated little differently.”

It’s easy to conjure an image of a mega-rock-star, accustomed to privilege, luxury, and historically lax treatment by police authorities around the world (without a passport, Paul once talked his way into France), to be devastated with trembling fear while in “virtually solitary confinement.”

Likewise accustomed to confinement in hotel rooms, limos, and dressing rooms during the touring years of the Beatles, Paul resolved to make the most of the ordeal that Norman says “could have broken a far more physically robust man.” What could easily have been a time of despondency was instead hilarious, illuminating one of Paul’s strategies for dealing with the emotional crevices of life:

“After a few days, I [Paul] became like Steve McQueen in The Great Escape. My natural survival instinct and sense of humor started to kick in… I’m going to be the first up when the light goes on, the first with his room cleaned, the first who gets to wash and do this teeth.”

Paul learned to communicate with inmates, who spoke little or no English, by shouting well-known Japanese brands: “Toyota!” or “Kawasaki!” His neighboring cellmates would respond, “Johnnie Walker!”

He joked around with the convicts, once making a “terrifying individual” jailed for murder “roar with laughter.”

Inescapably famous, he was inevitably requested — by the same man, a murderous “yakuza or Japanese mafioso” — to sing a capella “Yesterday.” He wisely agreed. Despite the guard’s half-hearted demand for silence, Paul gave a three-song encore.

He introduced a game, which originated from his time as a Beatle often trapped in hotel rooms or the studio, called “Touching the Highest Place on the Wall.” He usually won.

“His fear of rape receded,” writes Norman, “so much so that when offered a bath in private he elected to use the communal showers” where his mullet-esque hair towered over his “slightly-built” Japanese shower-mates while he led group singalongs.

This transformation occurred over a span of little more than one week.

Paul’s approach to dealing with imprisonment loudly echos beliefs fundamental in Stoic Philosophy. The Stoics emphasize the essential life-skill of teasing out things inside and outside of your control, and focusing on the things you can control.

The first-century Greek slave-turned-stoic-schoolmaster Epictetus stressed to his students this invaluable skill:

“So in life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control.”

Seneca the Younger, coming to his life’s end while Epictetus was just a child, wrote:

“Floods, or fires, will cause us loss. And we cannot change this order of things; but what we can do is to acquire stout hearts, worthy of good men, thereby courageously enduring chance and placing ourselves in harmony with Nature.”

With a stout heart and noble spirit fitting his knightly title, he refused to let external circumstances invade his mind. Norman reveals Paul’s mindset during this time:

“After so many years of limitless power and free will — and the stresses, both external and self-inflicted, that went with them — he found himself almost relishing the bleak simplicity, solitude and utter powerlessness of his prison life. ‘Suddenly’ he would remember, ‘I didn’t have to do the job any more.’ Far from penance, it came as a relief to lose all the myriad trappings of being Paul McCartney — even his very name — and revert to his status long ago when he’d first known John and George, as ‘just one of the lads.’”

On tour in Scotland in 1960, two decades prior Paul’s time as a “Japanese jailbird,” the Beatles traveled from gig to gig in a van boiling over with clashing adolescent egos. George Harrison remembered returning home from the tour “like orphans… shoes full of holes, clothes a mess.”

No matter how obscure the venues were on the outside or deserted on the inside, Paul used humor to get by, “greeting the Highland girls with an unfailing smile and ever-ready joke Scottish accent.”

Norman agrees that the Scotland tour “revealed Paul’s ability — one he would keep all his life — to get the most out of even the poorest situation.” In consonance with the mindset he adopted in Japanese prison, he again coupled his resoluteness with an unfailing sense of humor.

Stoic mindset complemented by a sense of humor were key ingredients in his elixir of the mind that brought him solace. It’s not a new tactic. Though peace of mind was tragically impossible in the trenches of the First World War, soldiers often turned to the only thing they had left in their control that could possibly lighten the darkest depths of humanity: humor.

A later tour with the Beatles illustrates another of Paul’s mental strategies for enduring hardship.

During residency in Hamburg’s Reeperbahn, “Europe’s most notorious red-light area, surrounded by strip clubs, prostitutes… pimps, transvestites and gangsters” the boys lived in ill-fitted quarters, where “rats scuttled over the bare concrete floor and the smallest rain-shower came dribbling through the ceiling onto the dingy little cots below.”

Not even nineteen-years-old, upon his return from Hamburg, Paul’s physical condition astounded his father and brother, the latter remembering Paul as “an emaciated skeleton.” To endure his sleep-deprived, squalid Hamburg experience, he retreated to the one thing truly under his own control — his thoughts.

He reframed into something useful how he perceived his environment. “He imagined himself,” Norman writes, “as a struggling artist, a young Picasso or Matisse, surviving in a Parisian attic. And one day, he thought, all of this would make ‘a chapter for the memoirs.’”

(Paul had done just that about his time in Japanese prison, writing a piece he called Japanese Jailbird. Sadly, he had only one copy printed, reserved only for his children when they got older, then locked up the manuscript.)

In the same vein, Marcus Aurelius famously wrote in his journal that “the impediment to action advances action. What stands in the way becomes the way.” Paul, time and again, would harvest the good out of bad situations, often resulting in the sweet melodies carrying his lyrics that have been replayed for decades to the ears of the world.

What was a home invasion by one of the contingent of Paul-adorers perpetually camped outside his London home became “She Came In Through The Bathroom Window.”

What was the sorrowful memory of a reassurance he’d often hear from his mother, who died when he was ten, transformed into the cathartic “Let It Be.”

What was the indignation Paul felt from seeing John Lennon neglect his own son Julian, just as John had been neglected by his father, became the hopeful message in “Hey Jude.”

Tim Ferriss, an avid evangelist of Stoicism, uses a similar mental model. On The Tim Ferriss Show, he describes the self-talk he sometimes employs when facing difficulties: “…even if this turns out poorly, it’s going to make a good story. Even if I hate this, it’s going to make a funny story.”

This last mental exercise isn’t actually a strategy for overcoming obstacles, but rather a decision-making process. It’s similar to the “regret-minimization framework” used by Jeff Bezos, in which projects himself into the future to the age of eighty. From the perspective of an old man, Bezos will ask himself what he thinks of whatever he is facing in the present.

And owing to this decision-making model, the world was blessed with one of history’s most poignant and thoughtful songs.

Paul with the Beatles, famously stepping onto American soil for the first time in 1964 (Photo: michellerocks)

In 1966, twenty-four-year-old Paul began writing songs, along with the other boys, for Revolver, a marked pivot toward maturity for the Beatles. Paul’s brilliant songs, Norman posits, “were not prompted by a bursting confidence, as was generally assumed, but by the insecurity from which no one ever imagined he could suffer.”

“As he so often did, he’d been wondering what would happen when he reached the inconceivable age of 30; by which time the whole Beatles thing would presumably be over and all he’d have left would be songwriting. Picturing himself in a middle-age, smoking a pipe and wearing a leather-elbowed tweed jacket… he set himself to write the ‘mature’ kind of song he’d need to then if he didn’t want to starve. And ‘Eleanor Rigby’ was the result.”

Norman calls it insecurity but I think it’s rather a stoic mental pre-exposure to tragedies, sorrows, and disappointments bound to happen in life. The Stoics obsessed about keeping present in your thoughts the idea that tragedy will strike you or your loved ones at any moment, to prepare yourself to endure such losses bravely and with noble spirit.

With humility and stoic forethought, Paul understood that nothing is permanent, and thanks to his envisioning of himself as an aging songwriter, we have the fortune of having “Eleanor Rigby” in music history’s catalog.

Though still an “aging songwriter” to this day, Paul’s sense of humor is easily found. I had the good fortune of seeing Paul on tour in his seventies. Scanning the many signs in the crowd constructed by fans, he came across one that he read with amusement: “Sign my ass!” Paul responded, “Sign my arse? All right, let’s have a look.”

This article was originally published at thoughtmedley.com.

Couple Paul’s Stoic strategies for dealing with difficulty with that of fellow performer and billionaire Jerry Seinfeld’s, or with the Stoic Philosophy found in the music of the Grateful Dead.

(This article contains Amazon Affiliate links to show you where to find the invaluable resources mentioned within.)

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Bradley Calvin

Business school grad, operations leader for a Fortune 500 company and author of the blog thoughtmedley.com where I write about business, history, music and more