20 Years of Latitude: The Most Important Illustrator

For twenty years, Latitude has been a home for creativity in all its forms – from words that move us to performances that reshape us and images that stop us in our tracks. Some art speaks softly; some reaches straight for the heart. This illustrator has the power to do both.

Most Important Illustrator cover image

The best illustrations capture what words alone cannot: a moment, a feeling, a truth. Over the last twenty years, we’ve seen images that comfort, challenge, reassure, and remind us what it means to be human. As we celebrate two decades of Latitude, we’re honouring the artists whose work has helped shape how we see the world. This year, we’re proud to recognise one illustrator whose influence has stretched far beyond the page.

OUR CHOICE

Most Important Illustrator: CHARLIE MACKESY

From the moment we first encountered Charlie Mackesy’s drawings, we recognised their profound approach – gentle, honest, and disarmingly human. Long before his global recognition, Charlie’s work already carried the qualities that define him now: warmth, vulnerability, and an instinct for saying the quiet thing people most need to hear. Watching his journey unfold has been nothing short of extraordinary. Few illustrators have touched as many people quite like Charlie Mackesy.

Charlie began his career as a cartoonist for The Spectator, before illustrating books for Oxford University Press. For years, he worked like many artists do – steadily creating illustrations, paintings, and bronzes that appeared in many spaces such as galleries, public spaces, cafés, and private homes. He lived and painted in South Africa, across sub-Saharan Africa, in the US, and across the UK, developing a practice shaped by curiosity, compassion, and a belief that art should be accessible to everyone.

This was not the story of an overnight sensation. It was a story of decades spent honing a craft quietly, earnestly, and with a rare emotional honesty.

Charlie Mackesy - Early work (painting)

The Royal Albert Hall

If you’d been looking for Charlie in his earlier years, you might have found him drawing outside the Royal Albert Hall – a building he sketched so many times he’s joked he could draw it blindfolded.

Charlie Mackesy - Royal Albert Hall Painting

Lockdown, Loss, and the Courage to Be Vulnerable

During the pandemic, Charlie began posting small drawings online that he called “little marks on paper,” as a way to comfort others and steady himself during a time of anxiety and isolation. Hospitals put his illustrations on walls and screensavers, teachers taped them in classrooms, and friends sent them to one another to feel closer. One cartoon in particular reframed vulnerability as a type of strength – showing that asking for help, expressing uncertainty, or choosing kindness were acts of enormous bravery. This message resonated globally, becoming a cultural touchstone during a moment when the world desperately needed gentleness.

Charlie Mackesy - NHS Lockdown Illustration

His bestselling book The Boy, the Mole, the Fox and the Horse became a global phenomenon upon its release, breaking records for the most consecutive weeks in the Sunday Times Non-Fiction Chart and becoming the longest-running Sunday Times Non-Fiction Number One of all time.

Illustration extracted from The Boy, the Mole, the Fox and the Horse by Charlie Mackesy/Ebury Press

Illustration extracted from The Boy, the Mole, the Fox and the Horse by Charlie Mackesy/Ebury Press

Why Charlie Matters to Latitude

Charlie’s work embodies the essence of what our twentieth anniversary project celebrates: the moments and makers who defined the last two decades through truth. His illustrations remind us that gentleness can be radical, that honesty can be transformative, and that art – at its best – makes us feel less alone.

It feels only right that in this milestone year, we honour an artist whose work has helped the world find courage, connection, and hope. As we look back on the last two decades, we invite you to explore the creators and memories that shaped our shared journey.

As Latitude marks its twentieth anniversary, we are proud to name Charlie Mackesy as The Most Important Illustrator of the last 20 years – an artist whose work has not only captured the world’s imagination, but helped to heal it.

We look forward to sharing more moments, more artists, and more stories as we continue our journey through the last 20 years.

With love,
The Latitude Festival Team