Richard McCabe
Rupert
Kelly Macdonald
Olive
Geraldine Somerville
Lady O
Simon Williams
Zoo Director
Stephen Campbell Moore
Ernest
Shaun Dingwall
Alfred
Domhnall Gleeson
A. A. Milne
Mark Tandy
Portrait Photographer
Robert Portal
Headmaster
Mossie Smith
Sharon the Midwife
Richard Clifford
Toy Shop Manager
Margot Robbie
Daphne Milne
Phoebe Waller-Bridge
Mary Brown
Nico Mirallegro
Cooper
Richard Dixon
MC at Pageant
Vicki Pepperdine
Betty
Sarah Jayne Butler
Winning Mum
Alex Lawther
Older Christopher Robin Milne
Bentley Kalu
American Cop
Will Tilston
Christopher Robin Milne
Simon Connolly
Radio Host
Nick Blakeley
Zoo Photographer
Allegra Marland
Fan 1
Ann Thwaite
Pageant Dignitary
Nicholas Richardson
Newspaper Man
Mark McKerracher
Groupie 1
Victoria Bavister
Mother at Zoo
Tommy Rodger
Douglas Minor
Rolan Bell
American Cop