Genius
A footballing genius who became an all-time hero of the Wearside club, his capricious nature often set him against football's establishment.
A Yorkshireman from Bradford, he played as an amateur for Bradford Park Avenue and, having been sacked as a member of Arsenal's ground-staff, two years earlier, he signed on as a professional with the club, at the age of 17, on Christmas Day 1939.
"It was during the war and illegal to sign a contract on Christmas Day," he later recalled, "but I didn't care and neither did the club. It was all I ever wanted to do."
Ironically, he was a Bradford City fan and such was his love for the game that he turned out for Park Avenue in the morning before guesting for City in the afternoon.
After six seasons at the Yorkshire club Len Shackleton joined Newcastle United for the then princely sum of £13,000. He scored six goals on his debut, still a club record, during The Magpies' 13-0 thrashing of Newport County.
His time in Newcastle was short-lived. After a mere 18 months at St James's Park, during which he scored 25 times in 57 appearances, he was lured to Sunderland for £20,500. The rest of his career would be played out against the backdrop of the Roker Roar.
Record
During his 11 years with Sunderland, Shackleton reached two FA Cup semi-finals and narrowly missed out on a championship medal. He holds The Wearsiders' post-war record, having scored 101 times in 348 games.
As well as illuminating the field with dazzling displays of skill, Len Shackleton gained the deserved reputation as 'the clown prince of football'. Tales of his antics have passed into football legend.
On one occasion, 2-1 up against Arsenal with 5 minutes to go, he dribbled the ball into The Gunner's penalty area before standing on the ball, pretending to comb his hair while looking at his watch.
Showman
He once hoofed the ball into a huge snowdrift on the cricket pitch at Sheffield United's Bramall Lane while Newcastle were 2-0 up in an FA Cup tie and, on numerous occasions, he mocked opposition full-backs by playing one-two's with the corner flag.
But such showmanship did not endear him to everyone. England's long-standing manager Walter Winterbottom tried to make Len Shackleton conform.
"If only Len would come half-way to meet the needs of the team there wouldn't be many to touch him," he once complained. In 1954, Shackleton got his chance.
Controversy
In a thrilling encounter at Wembley, which was perhaps his finest moment, England beat the then World Champions, West Germany 3-1, Shackleton himself scoring.
The following year he published his autobiography. Entitled "Clown Prince of Soccer", the book famously contained a chapter headed: "The Average Director's Knowledge of Football".
At the foot of the now legendary empty page was a note reading "This chapter has deliberately been left blank in accordance with the author's wishes."
Scathing
Len Shackleton retired from football in 1957. Though he lit up the domestic scene, his curtailed international career owes much to England selectors like the one who refused to pick him, "because we play at Wembley stadium, not the London Palladium."
In retirement 'Shack' was scathing about the tiny sums paid to him and his contemporaries, while keeping a weather eye on other clown princes, like Paul Gascoigne.
Len Shackleton's unconventional approach to the beautiful game may not have been to everyone's taste but, to countless thousands who saw him weave his magic in those austere post-war days, his memory will live every bit as large as today's cossetted superstars.