The best books with “difficult” protagonists

Charlene Challenger Author Of The Voices In Between
By Charlene Challenger

Who am I?

I find “difficult” characters fascinating because their humanity isn’t easily discerned. They’re often complex and richly drawn and show us aspects of ourselves we may not want to admit to others. Examining the ugly, the hidden, can be exhilarating.


I wrote...

The Voices In Between

By Charlene Challenger,

Book cover of The Voices In Between

What is my book about?

Adoni lives in a downtown apartment with her mother, an abusive alcoholic. One evening, she finds herself drawn to the enchanting voice of a man singing in the alley beneath her bedroom window. The man brings Adoni to The Welcome, a colony of the In-Between world, where young people who have been rescued from harm are kept safe by their sworn immortal protectors, the Pipers. But when The Welcome is attacked by Changelings—led by the vicious and charismatic Sylvester—and a centuries-old grudge spills over the edge and threatens to destroy the colony and everyone who lives there, Adoni must find the strength and courage within to stop the oncoming war.

The books I picked & why

Shepherd is reader supported. We may earn an affiliate commission when you buy through links on our website. This is how we fund this project for readers and authors (learn more).

Never Let Me Go

By Kazuo Ishiguro,

Book cover of Never Let Me Go

Why this book?

Kathy, Tommy, and Ruth are boarding school students of Hailsham, where they are educated and protected by adults known as “guardians.” The students of Hailsham are clones, bred so that their organs will one day be harvested and donated. Donations are made until the clone “completes” – a euphemism for their inevitable death. Despite knowing this, Kathy, the narrator of the novel, and the other characters accept their fates. They don’t protest or rise against the system that sees them as commodities; instead, they choose to distract themselves by creating and maintaining an insular mythos about their world. That Kathy tacitly consents to her own destruction is perhaps the most difficult aspect of the novel to accept. Never Let Me Go is an incredible, heartbreaking masterpiece. 

Never Let Me Go

By Kazuo Ishiguro,

Why should I read it?

9 authors picked Never Let Me Go as one of their favorite books, and they share why you should read it.

What is this book about?

One of the most acclaimed novels of the 21st Century, from the Nobel Prize-winning author

Shortlisted for the Man Booker Prize

Kazuo Ishiguro imagines the lives of a group of students growing up in a darkly skewed version of contemporary England. Narrated by Kathy, now thirty-one, Never Let Me Go dramatises her attempts to come to terms with her childhood at the seemingly idyllic Hailsham School and with the fate that has always awaited her and her closest friends in the wider world. A story of love, friendship and memory, Never Let Me Go is charged throughout with a sense…


The Door in the Mountain (The Ariadne Series)

By Caitlin Sweet,

Book cover of The Door in the Mountain (The Ariadne Series)

Why this book?

Set against a beautiful, violent landscape, The Door in the Mountain is the story of Ariadne, a young princess navigating her culture’s customs and her personal responsibilities. In Ariadne’s world, the course of one’s life is determined by whether one has a “godmark” – a special gift or ability granted by the heavens. Ariadne desperately wants to be godmarked like her brother and parents. That desperation fuels a mean streak that, at times, turns to downright cruelty. Caitlin Sweet is a master of characterization, and as a reader, I can’t help but sympathize with Ariadne’s longing to fit in with her family – to be considered their equal in all aspects – even when her words and actions are despicable to those around her. 

The Door in the Mountain (The Ariadne Series)

By Caitlin Sweet,

Why should I read it?

1 author picked The Door in the Mountain (The Ariadne Series) as one of their favorite books, and they share why you should read it.

What is this book about?

Ancient Crete: a place where a beautiful, bitter young princess named Ariadne schemes to imprison her godmarked half-brother deep in the heart of a mountain maze, where a boy named Icarus tries, and fails, to fly--and where a slave girl changes the paths of all their lives forever.


Lolita

By Vladimir Nabokov,

Book cover of Lolita

Why this book?

Lolita features one of the most hateful of all protagonists in 20th century literature. A sniveling, sputtering hypocrite, Humbert Humbert gleefully hangs his misanthropy, his frustrated sexuality, his pathetic mediocrity, around the neck of a child, and changes the course of her life forever. That Humbert is a pedophile is undeniable; that he unapologetically recounts his crimes with such beautiful lyricism is truly terrifying. The novel is best read with a modern lens. This is not, as is so often touted, a controversial love story; it is a brilliant, unnerving satire about western patriarchy and rape culture that grows more and more disturbing as time goes on.

Lolita

By Vladimir Nabokov,

Why should I read it?

8 authors picked Lolita as one of their favorite books, and they share why you should read it.

What is this book about?

'Lolita, light of my life, fire of my loins. My sin, my soul. Lo-lee-ta: the tip of my tongue taking a trip of three steps down the palate to tap, at three, on the teeth. Lo. Lee. Ta.'

Humbert Humbert is a middle-aged, frustrated college professor. In love with his landlady's twelve-year-old daughter Lolita, he'll do anything to possess her. Unable and unwilling to stop himself, he is prepared to commit any crime to get what he wants.

Is he in love or insane? A silver-tongued poet or a pervert? A tortured soul or a monster? Or is he all…


Intimacy

By Hanif Kureishi,

Book cover of Intimacy

Why this book?

Jay, a selfish, self-absorbed screenwriter, reflects on his failings as a lover, husband, and friend on the eve of leaving his wife and children. From the way Jay describes his marriage and his approach to fatherhood, it’s clear he’s more than willing to throw his comfortable life away and damage three innocent people for no other reason than he’s bored, shallow, and desperate to blame his incompetency on those closest to him. What keeps the reader engaged is how painfully funny it all is – Jay’s obliviousness provides ample opportunity for mature audiences to chuckle and shake their heads at every meanspirited quip he makes at his family’s expense. By the end of the book, readers can only feel relief that he’s done them an incredible, and long overdue, service.

Intimacy

By Hanif Kureishi,

Why should I read it?

1 author picked Intimacy as one of their favorite books, and they share why you should read it.

What is this book about?

'It is the saddest night, for I am leaving and not coming back.'

Jay is leaving his partner and their two sons. As the long night before his departure unfolds he remembers the ups and downs of his relationship with Susan. In an unforgettable, and often pitiless, reflection of their time together he analyses the agonies and the joys of trying to make a life with another person.


A Christmas Carol

By Charles Dickens,

Book cover of A Christmas Carol

Why this book?

At once ghost story and scathing social commentary, this holiday classic recounts the night Ebeneezer Scrooge is visited by three spirits concerned with his welfare. Scarred by his experience growing up in a miserable boarding school, Scrooge rejects kindness toward his fellow man in favour of the financial gain afforded him by the industrial revolution. Over the course of the evening, the spirits show Scrooge the life he came from, the life he has, and the kind of death that awaits him if he fails to reconnect with his humanity. Scrooge speaks one of the cruelest lines of dialogue in English literature: “If they would rather die, they’d better do it, and decrease the surplus population." That we continue to root for his redemption is a testament to Dickens’ genius. 

A Christmas Carol

By Charles Dickens,

Why should I read it?

12 authors picked A Christmas Carol as one of their favorite books, and they share why you should read it.

What is this book about?

Tom Baker reads Charles Dickens' timeless seasonal story.

Charles Dickens' story of solitary miser Ebenezer Scrooge, who is taught the true meaning of Christmas by the three ghosts of Christmas past, present, and future, has become one of the timeless classics of English literature. First published in 1843, it introduces us not only to Scrooge himself, but also to the memorable characters of underpaid desk clerk Bob Cratchit and his poor family, the poorest amongst whom is the ailing and crippled Tiny Tim.

In this captivating recording, Tom Baker delivers a tour-de-force performance as he narrates the story. The listener…


5 book lists we think you will like!

Interested in a middle age man, cloning, and Greek mythology?

7,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about a middle age man, cloning, and Greek mythology.

A Middle Age Man Explore 9 books about a middle age man
Cloning Explore 7 books about cloning
Greek Mythology Explore 47 books about Greek mythology

And, 3 books we think you will enjoy!

We think you will like My Sister, the Serial Killer, The Road, and A Clockwork Orange if you like this list.