From a feminist retelling of Moby-Dick to a fresh look at Cinderella from the perspective of her stepsister, the longlist for the UK’s top children’s book prize, the Carnegie Medal, is packed with reimaginings of classic stories.

Established in 1936, the Carnegie has been won by some of the UK’s best-loved children’s authors, including Noel Streatfeild and CS Lewis. The 20 books in the running this year range from Kit de Waal’s first young adult novel, Becoming Dinah – a reimagining of Moby-Dick in which a teenage girl sets off on a trip in a camper van with a grumpy one-legged man – to Jennifer Donnelly’s take on Cinderella, Stepsister, and Sharon Dogar’s Monsters, about the creation of Mary Shelley’s Frankenstein.

A host of picture books up for the Kate Greenaway medal for illustration also give fresh takes on the classics. And the Ocean Was Our Sky, illustrated by Rovina Cai and written by Patrick Ness, tells the story of Moby-Dick from the perspective of the whale; Quill Soup, illustrated by Dale Blankenaar, is an African retelling of the European folktale Stone Soup; and Mary and Frankenstein, illustrated by Júlia Sardà and written by Linda Bailey, is another title to riff on the making of Frankenstein.

This year also marks a first for the prize: Annet Schaap’s story of a lighthouse keeper’s daughter, Lampie, translated from Dutch by Laura Watkinson, is the the first translated book to be longlisted for the Carnegie. Chair of judges Julia Hale called it “as satisfyingly dark and light as the best fairy story adventures”.

Taking as their mission “to inspire and empower the next generation to shape a better world through books and reading”, and focusing on finding an “outstanding reading experience”, judges also found a strong theme of homelessness and identity in the longlisted novels. In Susin Nielsen’s No Fixed Address, a boy and his mother live in a camper van, one step from homelessness, while in former winner Sarah Crossan’s Toffee, a teenager runs away from home and is taken in by an elderly woman with dementia. Angie Thomas’s On the Come Up follows an aspiring rapper trying to escape the poverty of her neighbourhood, while Nikesh Shukla’s The Boxer, about the aftermath of a racist attack, is “brilliantly nuanced”, said Hale, and left judges “simultaneously bruised, reeling and uplifted”.

Hale said that among the 162 submissions for the two medals, there were lots of books about social media and the internet. But the titles chosen by a volunteer team of 14 children’s and youth librarians from across the UK were “more about universal things, like families and friendships and the way children and young people navigate the sort of challenges that they face in the world”.

“Through writing and illustration, the authors and artists offer children and young people stories of hope, discovery and understanding about themselves and the world they live in,” said Hale. “There is a strong emphasis in the longlists on how young readers can navigate that journey, through relationships with families and friends and from learning more about themselves.”

The shortlists for both prizes will be announced on 19 March, and the winners on 17 June.

2020 CILIP Carnegie Medal longlist

The Black Flamingo by Dean Atta, illustrated by Anshika Khullar

A Pocketful of Stars by Aisha Bushby

Toffee by Sarah Crossan

Becoming Dinah by Kit de Waal

Louisiana’s Way Home by Kate DiCamillo

Monsters by Sharon Dogar

Stepsister by Jennifer Donnelly

Lenny’s Book of Everything by Karen Foxlee

Nowhere on Earth by Nick Lake

Lark by Anthony McGowan

The Skylarks’ War by Hilary McKay

No Fixed Address by Susin Nielsen

Inkling by Kenneth Oppel

Patron Saints of Nothing by Randy Ribay

Lampie written and illustrated by Annet Schaap and translated by Laura Watkinson

Voyages in the Underworld of Orpheus Black by Marcus Sedgwick and Julian Sedgwick, illustrated by Alexis Deacon

The Boxer by Nikesh Shukla

On the Come Up by Angie Thomas

Girl. Boy. Sea. by Chris Vick

Paper Avalanche by Lisa Williamson

2020 CILIP Kate Greenaway Medal longlist

Captain Rosalie illustrated by Isabelle Arsenault, written by Timothée de Fombelle and translated by Sam Gordon

Wisp: A Story of Hope illustrated by Grahame Baker Smith and written by Zana Fraillon

Quill Soup illustrated by Dale Blankenaar and written by Alan Durant

B is for Baby illustrated by Angela Brooksbank and written by Atinuke

And the Ocean Was Our Sky illustrated by Rovina Cai and written by Patrick Ness

Fanatical About Frogs written and illustrated by Owen Davey

Voyages in the Underworld of Orpheus Black illustrated by Alexis Deacon and written by Marcus Sedgwick and Julian Sedgwick

Lubna and Pebble illustrated by Daniel Egneus and written by Wendy Meddour

When Sadness Comes to Call written and illustrated by Eva Eland

The King Who Banned the Dark written and illustrated by Emily Haworth-Booth

You’re Snug With Me illustrated by Poonam Mistry and written by Chitra Soundar

The Iron Man illustrated by Chris Mould and written by Ted Hughes

The Suitcase written and illustrated by Chris Naylor-Ballesteros

The Undefeated illustrated by Kadir Nelson and written by Kwame Alexander

The Dam illustrated by Levi Pinfold and written by David Almond

Mary and Frankenstein illustrated by Júlia Sardà and written by Linda Bailey

Little Wise Wolf illustrated by Hanneke Siemensma, written by Gijs Van der Hammen and translated by Laura Watkinson

Tales from the Inner City written and illustrated by Shaun Tan

Child of St Kilda written and illustrated by Beth Waters

Planetarium illustrated by Chris Wormell and written by Raman Prinja