Back to the Future

‘O’ Magazine Changed the Publishing Industry

From its covers to introductions of household names, the publication proved Oprah to be a maverick

Jenisha Watts
Published in
6 min readOct 14, 2020
Cover of O Magazine with Oprah Winfrey on a Windows 95 desktop with a rainbow gradient background.

This story is a part of our Back to the Future series on how key moments in the year 2000 influenced similar events in 2020.

When I was in college, I read an article in O, The Oprah Magazine that I’ve held onto like a button. I was an undergraduate student at the University of Kentucky, and my myopic mind was not yet filled with the possibilities of life outside the state. I wanted a better life than the one I was handed as a girl, and college was my way out, but I had no idea where to start. Thankfully, I had a poetry professor named Nikky Finney, who gave a talk to the Black journalism student organization. She picked up a piece of chalk, and our eyes followed her fingers as she wrote on the blackboard: Ida B. Wells.

One day, Finney told me to meet her in the English Department. When I arrived at her office, she handed me a 9x12-inch envelope sealed with a gold clasp, my name written in caps on the front. It felt like a special assignment. I rushed back to my dorm to open it. Inside was an article torn from the pages of O magazine. I removed the pages from the envelope and saw a photo of Dr. Angelou showing all her teeth in a smile, while a grinning Oprah laid her head on Dr. Angelou’s leg. The words stood out like 3D as I sat in my dorm room and read every word in the interview. The article was from the December 2000 issue, the first year O magazine was published. By the time I read the piece, it was already seven years old, yet it had a profound effect on how I see life:

Oprah: I know you don’t believe in modesty.

Maya Angelou: I hate it. It makes me wary. Modesty is a learned affectation. And as soon as life slams the modest person against the wall, that modesty drops.

Oprah: So when you hear someone being modest…

Maya Angelou: I run like hell. The minute you say to a singer, “Would you sing?” and they say, “Oh, no. I can’t sing here,” I say, “Oops! I wonder, where is that train to Bangkok?”

Oprah: Because?



Jenisha Watts
Writer for

Jenisha Watts is The Undefeated’s general editor for culture. Her Twitter bio quotes the late Toni Cade Bambara: Don’t leave the arena to the fools.