‘One Day, Oprah Will Pay for Her Crimes’: Read an Excerpt from Ira Madison’s New Book (Exclusive)

Cultural critic Ira Madison III has appeared on The Late Show with Stephen Colbert, Watch What Happens Live with Andy Cohen, The Wendy Williams Show and the Netflix dramaYou. Now, the writer and host of the podcast Keep It is gathering his thoughts in a new essay collection.

In Pure Innocent Fun, out Feb. 4, 2025 from Random House, Madison examines his own life through the lens of pop culture, from The Fresh Prince of Bel-Air to Britney Spears.

Madison, a Black gay man from Milwaukee, Wis., “recounts the impact of some of his formative experiences including learning about gay sex from his mom’s Lil’ Kim CDs; the most devastating election of his adolescence — Jennifer Hudson’s 2004 American Idol elimination — and never getting his driver’s license in high school, making him just like Cher Horowitz in Clueless: “A virgin who can’t drive,'” according to the book’s synopsis.

Below, in an exclusive excerpt from Pure Innocent Fun, Madison reflects on how Oprah Winfrey impacted his body image.

One day, Oprah will pay for her crimes. I’m not talking about making snake oil salesmen like Drs. Oz and Phil famous or the 2018 film adaptation of A Wrinkle in Time; I’m talking about her documentation of her weight loss from the ’90s until now. If you were born in the ’90s, then Oprah has pretty much been the same size for most of your adolescence and adulthood. But for elder millennials, born in 1986 or earlier, and anyone older, Oprah’s journey with her weight has a very specific chokehold on you.

Oprah’s weight loss odyssey began with the November 15, 1988, episode (titled “Dreams Come True”) of her daytime talk show The Oprah Winfrey Show, when she announced that she’d dropped a significant amount of weight in four months. With a feathered bob and dressed in a size 10 pair of Calvin Klein jeans, black boots with a sexy but sensible heel, a glittery belt and a body-hugging black sweater, Oprah looked like your auntie who let you go to the corner store to buy her Newports rather than the oversize-blazer-and-pantsuit-wearing-middle-school­ science-teacher energy she’d formerly served.

And to further drive home the fact that she’d lost a lot of weight, she rolled out the exact amount in animal fat on a little red wagon. She wasn’t just hosting The Oprah Winfrey Show; she was doing shows, honey. Oprah was showing out, and as a result, “Dreams Come True” became the highest-rated episode of the program’s 25-year history (and it remains so).

Oprah has since expressed regret for this moment. In 2024, she hosted ABC’s  An Oprah Special: Shame, Blame and the Weight Loss Revolution to discuss her use of Ozempic, the antidiabetic medication also used for weight loss, and how she finally conquered her struggles with weight. In the special, she blames the media for bullying her into trying fad diets, starving herself, etc., over the years and how much shame she has for carting out that wagon of animal fat. In fact, she started to gain the weight back the day after shooting “Dreams Come True.”

I’m not here to hold Oprah to some morality that I don’t even have myself — I used a version of Ozempic prescribed to me in 2023. It worked well for a few months, until the Writers Guild of America strike happened and I ran out of money for it (and a gym membership), even with the discount from my insurance, so that was the end of that! The only issue I have with Oprah discussing her weight shame and then doing a special about how Ozempic finally helped her is how it’s really only about helping her. Which would be fine if the whole point of her talk show was about helping people. Every time she discussed weight over the years, it was all to justify to the public why she was on the latest fad diet. With Oprah, when there’s something to sell, objectivity always seems to go out the window.

The Oprah Winfrey Show debuted on September 8, 1986, and became incredibly influential because she sold relatability and not a sideshow. In 2002, Christianity Today described how she’d essentially become a spiritual leader to her viewers. Her friends became their new mentors. Dr. Phil became their therapist. Suze Orman became their financial planner. Dr. Oz became their doctor. Iyanla Vanzant became their life coach. Whatever books Oprah read, the people read.

This backfired after author James Frey was revealed to have fabricated or exaggerated parts of his memoir A Million Little Pieces, which was an Oprah’s Book Club pick. To save face, she invited him on the show for a public tongue-lashing. I don’t even remember if Oprah uttered the words “I feel like I have been duped” to Frey, but I always remember her saying them, so they’re real enough for me. Oprah taught me to go with what I feel, even if it’s not necessarily the truth. Oprah could convince us to do anything — and this authority communicated a warm relatability. Inexplicably, she became everyone in America’s weight-loss guru because Americans are experts at taking personal anecdotes as facts.

What Oprah hasn’t truly apologized for is that when she rolled 67 pounds of animal fat into millions of homes* through their TVs, she sparked an entire generation of unhealthy dieters. It was about fighting the media’s depiction of her, yeah, but there’s a reason Oprah’s Book Club selections sell out immediately. She has the Midas touch. But, sis, you know you were in physical pain with each and every fad diet you went on, yet you still went on TV and suggested other people try them. Maybe Oprah’s misery wanted some company: “If I have to starve myself to look good, then, s—, so does everyone else.”

* The year 1988 is too early for me to have a memory of this, but the number of times I saw it replayed through archival footage on pop-culture TV shows of the I Love the ’80s variety made it clear that this was Oprah’s villain arc.

From the book PURE INNOCENT FUN: Essays by Ira Madison III, to be published on Feb. 4, 2025, by Random House, an imprint and division of Penguin Random House LLC. Copyright © 2025 by Ira Madison III

Pure Innocent Fun by Ira Madison III comes out Feb. 4, 2025 and is available for preorder now, wherever books are sold.