Current Rupert artist Stuart Trotter is almost celebrating 20 magical years of creating Rupert Bear annuals. Since 2008, Stuart has carried on Nutwood’s rich tradition with warmth, imagination, and charm, ensuring Rupert’s adventures continue to delight fans old and new. In light of this the Northern Echo published a interview with Trotter about his work on Rupert.
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My 20 magical years creating the Rupert Bear annuals
27th August 2025, By Peter Barron
A County Durham artist is celebrating a milestone, conjuring up the adventures of a treasured children’s character.
AS he approaches his 20th year as the official illustrator of the Rupert Bear annuals, Stuart Trotter can draw on a deep well of magical memories.
And he’s determined to stay true to the traditions of a character who can be traced back more than a century.
“As long as Rupert’s in my hands, he’s not going to be brought into the modern world – it would be like Tolkien giving Gandalf a mobile phone!” says Stuart, who has found his way from County Durham to a world of adventure through his talent for drawing.
The 90th Rupert annual will be published at the end of this month, and Stuart has again written and illustrated the stories that make up the book, featuring the lovable little bear in the red jumper, yellow checked trousers and matching scarf.
Always working a year ahead, this is the 2026 annual. Stuart’s first as author and illustrator was the 2007 annual, and the 2027 version has just been commissioned, so the creative process is about to start all over again. It takes a year of painstaking work, creating five stories, with 56 panels per story, but it’s a labour of love for Stuart, who fell in love with Rupert as a four-year-old in 1959 – the year Father Christmas first delivered the Rupert annual to the Trotter family's terraced home in the former pit village of Ferryhill.
“I loved it so much that I asked for the Rupert annual every Christmas after that, and I still have to pinch myself to think that, all these years on, I’m now the author and illustrator,” says Stuart.
“It’s a joy and a privilege because Rupert’s a treasured part of English literature and, here we are, on the verge of the 90th annual coming out.The market these days is mainly grandads buying it for their grandchildren, keeping the magic going from their own childhood. "It's a traditional England they yearn for – a gentle time, with lots of kindness, mystery and good storytelling."
Stuart’s mum and dad were readers of the Daily Express, which was the long-established home of the Rupert comic strip, so the little bear was always part of the Trotter household. Young Stuart spent much of Christmas 1959 working on the colouring competition at the back of the annual – filling in in a scene depicting Rupert, Bill Badger and Algy Pug by a goldfish pond. However, the finished entry was never submitted because Stuart couldn’t bear it to be cut out of his precious book.
Rupert was born on November 8, 1920, when he first appeared in the Express after Mary Tourtel, the artistic wife of the paper’s night editor, was commissioned to produce a cartoon to boost flagging sales. Alfred Bestall, who had been an illustrator with Punch, took over as the Rupert artist and storyteller in 1935, and continued into his nineties. A sign of Rupert’s popularity was that, during World War Two, the Express decided against axing him for fear of damaging national morale. Having grown up with Rupert, Stuart always enjoyed art at school, though it never crossed his mind that he might one day make a living from it. However, he studied graphic design at Coventry School of Art and Design before starting work as a freelancer.
In return for three hours free work a week, he was given desk space in Sally Williams' Design Studio in Coventry, and his career developed from there. Further down the line, he was doing some freelance work on Wallace and Gromit for London publishers, Simon & Schuster, when the Daily Express got in touch with an archive project for Rupert.
Stuart was asked to do a sample illustration, sticking to the revered Bestall style, and it was well received. A few weeks later, another publisher, Egmont, won the rights for the Rupert annual and Stuart’s sample was sent off. “Three months later, I got a call from Egmont asking if I wanted to do the Rupert annual and the rest is history," recalls Stuart. It was a case of being in the right place at the right time.”
When the news came through, Stuart’s wife and daughter were in a restaurant in Falmouth, so he phoned reception to order a bottle of champagne to be delivered to their table with a note saying: “This is from Rupert.” Stuart’s wife initially turned the bubbly away, telling the waiter: “Sorry, we don’t know anyone called Rupert!”
Nevertheless, it marked the start of a long, happy association with Rupert, which has now lasted almost two decades.
Apart from Rupert, Stuart has also illustrated a range of other much-loved characters, including Winnie the Pooh, Thomas the Tank Engine, The Animals of Farthing Wood, and Postman Pat. He runs his own business, Rockpool Children’s Books, designing, writing, illustrating, and producing.
Earlier this year, a Rupert mural, featuring ten illustrations by Stuart, was unveiled at the railway station in Surbiton, hometown of Alfred Bestall. The mural – printed and installed by Darlington company Screentech – tells the story of Rupert going on holiday from the station to Grey Rocks Cove.
In September, Stuart will travel to South West London for the Surbiton Festival to sign copies of the new Rupert annual, and he already has designs on reaching a new milestone. "My aim is to illustrate the 100th annual – so there are a lot more adventures to enjoy before we part company," he smiles.
