How to Become a Cheryl Strayed Stan in Time for the 'Wild' Author's Next Buzzy Adaptation

Her book 'Tiny Beautiful Things' is now a Hulu miniseries starring Kathryn Hahn.

Cheryl Strayed is best known for her 1995 decision to hike the Pacific Crest Trail—which, at more than 1,000 miles, is not a path for the faint of heart. She wrote about the experience in her bestselling 2012 memoir Wild: From Lost to Found on the Pacific Crest Trail, which was adapted into an Oscar-nominated film produced by and starring Reese Witherspoon in 2014.

But Strayed had a devoted fan-base even before then. For two years prior to publishing Wild, Strayed anonymously wrote the advice column "Dear Sugar," which amassed a huge following online, for a site called Rumpus. In The New Republic, Ruth Franklin called the then-mystery writer, who famously referenced her own real-life experiences in her columns, “the ultimate advice columnist for the Internet age, remaking a genre that has existed."

In July 2012, months after revealing her identity and publishing Wild, Strayed released Tiny Beautiful Things, a collection of her Dear Sugar columns. On April 7, a small-screen adaptation of that book, starring Kathryn Hahn, will stream on a Hulu (all eight episodes will drop at once).

Here is everything you need to know about Cheryl Strayed's wildly successful career—and how to read her books in order.

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Who is Cheryl Strayed?

Strayed is an author and podcast host who formerly worked as a newspaper reporter. As a teen, Strayed lived in a house that her family built themselves—and it didn't feature indoor plumbing until after Strayed moved out.

Professionally, Strayed got her start by publishing essays in Vogue, The New York Times Magazine and more.

What is Cheryl Strayed most famous for?

Strayed released her memoir, Wild: From Lost to Found on the Pacific Crest Trail, on March 20, 2012, to enormous acclaim and success. Reese Witherspoon, who almost immediately optioned the book, went on to star as Strayed in the Oscar-nominated film adaptation.

The book is about Strayed's decision to hike the 1,100-mile trail in 1995 while on a path toward self-discovery. Strayed told Oprah Winfrey that she was inspired to take the hike after her mother's death in 1991.

"My mother's death brought me to what I think of as my most savage self," she said. "It stripped me of the one thing I needed. My mother was the taproot of my life. And suddenly, I didn't have that anymore. I had wild love for my mother. I had wild sorrow. And then I went wild. I went wild into my life."

When did Cheryl Strayed hike the Pacific Crest Trail?

Strayed began her hike of the Pacific Crest Trail in 1995, three years after she first committed to the prospect. Strayed admitted to Winfrey that she went back and forth on the decision, but ultimately felt that embarking on the hike was about something much bigger than herself.

"I was failing in so many ways in my life, and my biggest fear was that I would fail again on this trip," she explained. "I simply could not fail. I was too proud to call my friends and say, 'You know how I was gonna hike that trail? I didn't do it.' So, no matter what, no matter what, I had to get that pack attached to me and go. It didn't feel good. It felt terrible. It was really painful. But I had to do it, and now I see why: I needed to carry that heavy weight. I needed to carry the weight that I couldn't bear."

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Strayed has also noted that being on the trail gave her a lot of time to really dig into her own life and decide how she wanted to live it going forward. In an interview with Vogue, she acknowledged that hiking such a long trail can be boring at times, but doing so isn't without a reward.

"One thing any backpacker will tell you is that it’s tedious and monotonous," she said. "You’re bored sometimes, so you really have to make the fun in your head. I would find myself lost in long, uninterrupted sessions of thinking deeply about important relationships in my life."

What is Dear Sugar?

In March 2010, Strayed begin writing "Dear Sugar," an advice column for Rumpus—only she didn't reveal her true identity at the time (and wouldn't for another two years).

In the column, which promised “the by-the-book common sense of Dear Abby and the earnest spiritual cheesiness of Cary Tennis and the butt-pluggy irreverence of Dan Savage and the closeted Upper East Side nymphomania of Miss Manners," Strayed revealed intimate details about her own life while dispensing wisdom on topics like infidelity, friendship, jealousy and more.

After revealing her identity in 2012, she told The New Yorker, "I think a lot of people assume Sugar’s anonymity granted me the freedom to write with that sort of intimacy, but I think it’s the form itself. In each column I am doing many things, but first and foremost I am writing a letter to one person about a problem he or she is having, which, by its very nature, is an intimate exchange. One of the most fascinating things about writing the column has been the opportunity to explore the direct address in a public arena."

Strayed penned her final Dear Sugar column in 2012, but revived the series as a podcast ten years later, in December 2022.

Are Reese Witherspoon and Cheryl Strayed friends?

Strayed asked her agent to send a copy of Wild to Reese Witherspoon ahead of the book's release in 2012. The actress was immediately captivated by the memoir, and soon bought the rights to make it into the 2014 film she starred in.

Strayed and Witherspoon (along with Laura Dern) became friends while making the film.

The author told Indie Wire that she and Witherspoon bonded in a lot of ways. "Reese and I have an awful lot in common," she said. "For one thing, Reese has been an actress since she was a kid. We’ve both had this really strong drive to essentially make art in the world—me through words and her through acting. So our trajectories were different, and we’ve had different experiences along the way, but I think there’s something kindred about me and Reese."

What type of books does Cheryl Strayed write?

Strayed has written four books, including one novel, Torch (2006), and three nonfiction titles.

How to read Cheryl Strayed's books in order

Here is a chronological list of Cheryl Strayed's four books to date.

Torch (2006)

Torch follows Teresa Rae Wood, a waitress who is known for her radio show Modern Pioneers! As the character tells listeners, she's a survivor—a woman who took her two kids and left her first marriage without looking back. Sadly, the family is hit with personal tragedy and forced to grapple with fear and grief in a deeply human way.

Wild: From Lost to Found on the Pacific Crest Trail (2012)

Perhaps Strayed's most famous book, Wild: From Lost to Found on the Pacific Crest Trail is a detailed memoir about her decision to hike the Pacific Crest Trail in 1995. It was adapted into a film that was released in 2014.

Tiny Beautiful Things (2012)

Tiny Beautiful Things, a collection of the most celebrated moments from Strayed's Dear Sugar column, was tailor-made for her earliest fans. The book was adapted into a miniseries for Hulu, with all 8 episodes streaming on April 7, 2023.

Brave Enough (2015)

Strayed's most recent book is a collection of more than 100 inspirational quotes by the author herself.

Happy reading!

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