6 Best Oprah Book Club Books of All Time

Winfrey was a devoted fan of the Nobel Prize-winning author (she even starred in an adaptation of her book Beloved.) For her second-ever book club choice, she chose the elegiac and ambitious story of Macon "Milkman" Dead III, an African-American man living in Michigan from birth to death. Milkman is born in the chaos of a man's death and his life is defined by strife, familial drama, and the weight of his so-called inheritance. If you’ve never read Toni Morrison before, this is a great starting point.

This surreal drama of religious zealotry and colonialism was the June 2000 choice for the book club. Nathan Price is a preacher who packs up his family of four daughters and moves them to the middle of the Belgian Congo of the 1960s with plans to convert the locals to Christianity. The Price daughters – Rachel, Leah, Adah and Ruth May – and their mother, Orleanna, must contend with being intruders to this country and the stifling pressure of life in this strange land so unlike home. It’s an evocative read that makes you feel as though you’re stuck in the jungle with the Prices! 

A mercilessly bleak post-apocalyptic dystopian drama by the guy who wrote Blood Meridian may not have seemed like the natural choice for Oprah, but make no mistake: The Road is a very Oprah-esque choice! Yes, it’s pitch-black in its plot and one of the most depressing stories you’ll ever read, but there is hope in this tale of a father and son who fight to maintain a sense of purpose as they trail the ravaged remains of America. This one won the Pulitzer Prize, and for good reason. Just don’t read it on an off day.

Oprah loves a family saga. Many of her novel choices are multi-generational tales of legacy and identity. Middlesex is one of the most fascinating of the bunch, centred on three generations of a Greek-American family whose incestuous history leads to the birth of our protagonist, assigned female at birth but who slowly realizes he is intersex.

Jeffrey Eugenides is ambitious in his focus, blending classic Greek mythology with 20th century American immigrant mythmaking. Only his second novel, Middlesex won Eugenides the Pulitzer Prize.

It’s rare that Oprah picks more than one book for the month, but when she chose the acclaimed Marilynne Robinson, she knew she had to take on all four titles in her legendary Gilead series: Gilead, Home, Lila, and Jack.

The quadrilogy is a moving, purposeful, and quietly revelatory saga of family, faith, and spirituality. The first book, published in 2004 and a winner of both the Pulitzer and National Book Critics Circle Award, is an epistolary portrait of Reverend Ames, writing letters to his young son that reflect on his past. Barack Obama is one of the book's biggest fans.

When Oprah moved her book club to YouTube, she kicked off this new era with a short but startlingly good novella by Irish author Claire Keegan. Small Things Like These follows Bill, a coal merchant who grows convinced that the convent he delivers fuel to is a Magdalene laundry, an abusive forced home for "fallen women." His wife thinks he should keep his nose out of the church's business, but he cannot ignore the cruelty unfolding in his own town, part of a dark legacy that haunts Ireland to this day. The book was recently adapted into a movie, starring Oscar-winning actor Cillian Murphy.