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Which Oprah Winfrey Book Should I Read First?

With the prevalence of Oprah’s book club, it’s no surprise that many readers turn to Oprah Winfrey to find additions to their TBR pile. However, some readers turn to Winfrey, not for her latest book club pick but to read the books she’s written!

Oprah has written a variety of books, including her 2021 release, What Happened to You? and the timeless Journey to Beloved. But, whereas Oprah’s Book Club readers can pick up the newest addition and dive in with the rest of the book club, those who’re reaching for one of Miss Winfrey’s books will have a bit more of a challenge in determining which book to read first. This isn’t an impossible question, though—there are a few different ways you can approach reading Oprah’s own bibliography, one Oprah Winfrey book at a time.

Reading Chronologically


To read Oprah Winfrey’s written works in the order they were published, you’d want to begin with 1996’s Make the Connection: 10 Steps to a Better Body & Life, co-written by Winfrey and trainer Bob Greene. Winfrey supplies testimonials throughout this book, attesting to Greene’s methods and program as a tool that helped her feel better about her body and herself. If your shelves have a dedicated space for books about health and wellness, this older title is sure to be an excellent addition.

Reading in Reverse


Alternatively, you may decide to approach Oprah’s books in reverse chronological order, opting instead to start with her most recent release. In that case, you’ll be starting with What Happened to You?: Conversations on Trauma, Resilience, and Healing, co-authored by Dr. Bruce Perry, a renowned brain and trauma expert. In this book, the two reconsider trauma and the behaviors that arise in its aftermath, using deeply emotional insights to move the conversation from the blame-filled question of “What’s wrong with you?” to the more enlightened “What happened to you?”

Reading a Fan Favorite


As of this writing, Oprah’s What I Know For Sure is her highest-reviewed book according to Amazon. This keepsake collection unites the life lessons, inspiration, and revelations shared in O, The Oprah Magazine’s popular monthly column of the same name. The essays in this collection are arranged by theme, with subjects including joy, resilience, clarity, power, and connection, offering readers insight into this inspirational media mogul herself while inspiring them to transform their own lives.

Reading What Catches Your Eye


When it comes to an influential woman like Oprah, you’ll surely hear of her new releases beyond the limits of a bookstore or article like this. Instead, you may come across an excerpt or recommendation that brings a particular title to mind. For example, maybe you’re intrigued by Winfrey’s iconic Journey to Beloved, detailing her experience of bringing Toni Morrison’s classic novel Beloved to the screen. Oprah Winfrey portrayed the novel’s protagonist, Sethe, and developed her own spiritual connection to the project and this role, in particular—a connection that transformed her life ever since, as outlined in this look at the making of the film.

While Oprah’s Book Club may be the more popular source of new books to read, Miss Winfrey’s own bibliography has its own assortment of titles to choose from. Whether you’re interested in cinema, inspiration, wellness, or resilience, there’s a book by Oprah herself that’s sure to find a place of honor on your bookshelf. Start at the beginning and read through each release chronologically, pick up a particularly well-reviewed title from her collected work, or choose the first title that catches your eye. In any case, you’ll have plenty of books to choose from—and even more if you move on to her book club picks next.


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