The Funniest Books of the 21st Century

Here at Five Books, we love covering the shortlists for the annual Bollinger Everyman Wodehouse Prize for Comic Fiction. The judges are fantastic at flagging up new books with humorous elements—sometimes cosy, feel-good comedy and sometimes ‘serious’ literary fiction whose dark themes are offset by hilarious turns of phrase.

This year, to celebrate the prize’s 25th anniversary, its organisers decided to offer an extra award to recognise the ‘winner of winners’. To do so, they asked a group of judges—comedian Tatty Macleod, designer Patrick Grant, television presenter Claudia Winkleman, comic Sindhu Vee, and Hay Festival founder Peter Florence—to review every winning novel since the prize’s founding.

But how to choose the funniest book of the 21st century? Judge Tatty Macleod told Five Books: “‘Funny’ can be a complicated thing to ask of a book, because you are not always necessarily going to be laughing out loud. That’s a hard bar to hold a book to, especially if it’s over 300 pages. I can’t expect to be laughing out loud all the time.

“It’s more about whether the book is observationally funny, if it gives me an interesting perspective. Do I want to pick this book up? Is it like a warm hug? Because that’s what I look for in a funny book. Finding a book that captures that sense of lightness and escapism, or of going into a different world or a different life and losing themselves in that, and having a good chuckle along the way—that’s what I was looking for.”

Comparing older books with more recently published novels could be tricky, she noted. “It’s been an interesting exercise to see how humour and comedy adapt over time.” Nevertheless, it was a 2005 novel that ultimately won out, when the judges selected A Short History of Tractors in Ukrainian as their winner. Its author, the British-Ukrainian writer Marina Lewycka, died earlier this year, but reportedly was told of her triumph shortly before she passed away.

“A Short History of Tractors in Ukraine captures perfectly the hilarious complexity of family dynamics,” explained Tatty Macleod of the judge’s decision. “It deals marvellously with the shifting relationship with ageing parents. It’s as absurd as it is moving and a very worthy winner for the Vintage Bollinger Prize.”
Here’s the full list of previous winners of the Wodehouse Prize for Comic Fiction, to help you select your next humorous read.

2025

2024

2023

2022

2021

2020

2019

2018

Prize withheld ‘after judges failed to laugh‘

2017

2016

2015

2014

2013

2012

2011

2010

2009

2008

2007

2006

2005

2004

2003

2002

2001

2000