Gawker Readers Give Back: More Oprah Sightings and Horror Stories

Yesterday, one of Oprah's ex-employees sent us her tale of woe working at her media company, Harpo. Now a few more readers have come out of the woodwork to share their stories and sightings.

Working Out with Winfrey

Scott says he often spots the showbiz queen jogging near the lake.

Sometimes, I go bicycling along Chicago's lakefront early in the morning, and I see Oprah while she's jogging. She usually has one or two assistants with her who are wearing reflective gear.
Encountering "Jogging Oprah" for the first time is amusing because she looks so unlike her TV self without makeup. You see this large woman in a pink sweatsuit plodding along—head thrust forward in grim determination like an old bull—and you think: "Waaaaait... Could that be Oprah?" And then you get closer and you think: "Oh my God! It is Oprah!"
And then you think: "That's too bad..."

Getting Hired at Harpo

This Gawker reader once interviewed at Harpo. It didn't go well, clearly:

I had the strangest interview with the Oprah senior staff about 12 years ago. If it's possible to have a passive aggressive interview, then this was it.
I got the call to fly to Chicago to meet with the Executive Producer, Dianne Atkinson Hudson. So the Oprah staff arrange for my travel, putting me on an 11 am flight from NYC to Chicago. After I land, I take a cab over to the studios, where I wait for about an hour. They bring me in to meet Diane, who was a very serious person—I mean, an awful, "I'll-cut-your-throat" kind of serious. She tells me she wants me to meet someone else, but never specifies who this person is. This person is a senior producer-type and proceeds to interview me, but at no time does she introduce herself to me or does anyone give me an indication of what this lady's name is. As we say our goodbyes back in Diane's office, and I ask her what her name is, the silence just sliced right through me. She coldly tells me her name, and as I slither away, I know I am not getting a call back.

Oprah Goes Shopping

In the mid '90s, Susan waited on Oprah in a Chicago department store. Winfrey was worried her purchases wouldn't be expensive enough.

So, from 1990-95, I worked as an assistant manager at Marshall Field's State Street store in downtown Chicago. Oprah's "home store" was Water Tower Place, so I was quite surprised when O and her entourage (her hairdresser, and about 3 other hangers-on) showed up on my floor late on a Thursday afternoon.
A little background: When Oprah first arrived in Chicago, Field's supplied the wardrobe for her show. So, she had a lot of loyalty to us, and particularly a saleswoman in the "28 Shop" (higher-end/designer women's department). She was a very tiny, older Asian lady, and as I was briefed by the store manager, she would get any/all commissions on whatever Oprah purchased. Even though this lady had no idea about our ordering procedures. So basically, me and my people were going to have to do all the work, and get no credit for it. This rubbed me the wrong way immediately, but I had to roll with it.
I was told she was looking for a complete tablesetting (china, crystal, and silver) for, I think, 40 people. She came in and swanned around, surrounded by store brass, looking at stuff. Her underlings, especially the hairdresser, seemed to be having a lot more fun than she did, running around with stuff like kids in a candy store. I was asked to hover discreetly in case Oprah had any questions about an item, but not to try and engage her. At one point, I observed that she was holding a $1,000.00 St. Louis crystal pitcher, which is very fancy indeed, with lots of 24K gold applied to it. As she was chatting with the store muckety-mucks, she was swinging the pitcher casually by the handle, dangerously close to a display table. I stepped up and said, "Ms. Winfrey? Excuse me, but that pitcher is the only one of its kind in stock, and if it should break, the lead time is about nine months. Would you mind if I put it aside for you?"
I thought the store manager was going to die, right there. Anyway, she regarded me for a moment or two, then handed me the pitcher without a word. Meanwhile, her peeps had put together the following setting for her to look at:
- Bernadaud (high-end French) china, name of which escapes me, which was white with a multi-colored border of various fruits and a gold rim;
- A modern stemware pattern by Mikasa (low-end Japanese) which consisted of three sizes (water, wine, champagne flute) each in a different pastel color; and
- A very traditional, very ornate silver pattern.
By themselves, there was nothing objectionable about any of it; but combined, I have to say it looked like ASS. Nothing matched, style-wise, and each element was competing for attention. The hairdresser guy (Andre?) was especially enamored of the china, which Oprah called the "Tutti-Frutti" pattern, repeatedly. My gay male counterpart in the china section, who was also told to stay close to answer questions, took that as a gay slur.
Anyway, she never bought the pitcher, and we were given instructions to write up a drop-ship rush order for 40 or so, with accessories, of the Frankenstein table setting. Since it was so late, we couldn't contact the buying office until the next day, so my fellow sales leader (Glenn — he was also a great friend, and he died of AIDS complications a few years ago, otherwise he'd love to he telling you this as well) and I stayed a little late to write everything up. As we were leaving for the night, I made a bet with him that the order would be cancelled the next morning. I won. Oprah and her pals wasted several hours of our time, got one person extremely hyped over a possibly huge commission, and made a bunch of middle-aged men (the store bosses) clench their ass-cheeks, all for nothing. Glenn and I also had a theory that she was trying to drum up gossip that she would be hosting her wedding to Steadman at her Indiana farm soon (the items were to have been shipped there, and this was during the height of the "Oprah-Steadman engagement" period.)
Then about two weeks later, I was walking through the floor, and I hear a voice call my name. I turn, and see a really frumpy-looking African-American woman in a velour tracksuit. Her hair was pulled back and really frizzy and her skin looked like crap. Very bad acne/acne scars. Once she started speaking to me, I realized it was Oprah. Honestly, she is unrecognizable without the spackle/wig. Anyway, she was very nice, and asked me if I would offer my opinion on a china pattern she was looking at for her house. It was Villeroy and Boch (German, middle-range) "Petite Fleur." Very cute, kind of French-country, with a small, scattered floral design. I said, "What's not to like?" Oprah responded, "Well, it's not that expensive, and I don't want people who come to my house to think I'm cheap."
I was kind of stunned by that, and said something to the effect of: "I know that you could buy this entire store if you wanted to. Why on earth would you care what people think? If you like the design, it makes you happy, buy it. If not, don't." I almost offered to charge her more, if it would make her feel better, but I kind of sussed that the lady has NO sense of humor, especially about herself. Our encounter ended there. (I think I said I had to pee, or had some pressing tabletop business to attend to, and told her to have a nice day).

'In a Whirl, She Was Gone'

In 1993, Oprah sponsored a benefit for an educational development organization called Facing History and Ourselves. Winfrey enlisted local schoolchildren to participate in a fundraising event and this tipster—then only 13-years-old, but still afraid of Winfrey's reach—was among those picked to tape a TV spot promoting the fundraiser.

Five kids were driven over to Harpo with our teachers and FH & O leaders. We were excused from school to tape. We arrived in the studio, which I remember being smaller than I thought, but this was back in 1993 and I was 13. We were instructed to wear red and not hug Oprah. We could only shake her hand if she ventured to us first.
Mind you, this was a bunch of 7th and 8th graders.
So there we were, waiting for O to arrive, while an entire camera crew slouched and sloughed. She was 45 minutes late. And let me tell you, when she hit that stage with her people, you would have thought the Queen of England arrived. I've never seen so many people jump to their feet and alter their crumbly behaviors into sweet sycophants. The effect was incredible to my 13 year old mind.
She also has really bad skin, tons of acne scars, and wore tons and tons of makeup. There were spray colors in her hair so it illuminated on TV correctly. We taped the spot in two takes. Afterwards, her team tried to shuffle her out. But, she said she wanted hug us. They screeched to a halt.
Yes, I got a hug. Not to sound weird, but it was warm at first and then very cold and reserved. She pulled back after you hugged her.
In a whirl, she was gone. I came away thinking to myself that even with us kids, she wasn't as nice as on TV.

Oprah's Golden Jubilee

This ex-Harpo staffer says Oprah made some interesting comments at her birthday bash a number of years ago.

At her 50th birthday party in the back studio with Stevie Wonder she made a speech and I'll paraphrase the lovely racist remark that caught my ear: "I know I've made it because I have all these white people working for me!"
The other thing I'll say is that Harpo is one of the best and most consistent shows in town and you're lucky if you can work there, but they ain't union. One of my bosses worked there for 15 years, was married with two kids and worked an average of 65 hours a week before he was salaried with full benefits. This was not uncommon and divorce is incredibly common over there.

The Harrowing Tale of Harpo Hell

Finally, the pièce de résistance: This reader says she was fired for "not having the Harpo spirit," but not before accumulating some memorable moments from her time in Oprah's employ.

I worked at Harpo for about 3/4 years late '90s-early 2000s and I can corroborate the part of this story that alleges that the producers are all wickedly insane bitches.
I vaguely remember Carla but never worked with her directly so I am not entirely sure how true it is that she never worked all of the overtime she was paid for, but it wouldn't surprise me.
I started as a viewer mail processor, opening incoming mail, sorting the wheat from the chaff, throwing most of it in the shredder, helping myself to the books people sent in for O to read, the afghans people knitted her, a lot of scented candles, and got to eat the hell out of some delicious chocolate-covered strawberries some California company sent in hoping to get on her favorite things show (Sorry, dudes).
After a year, I was laterally promoted to the research department and a year or so after that they retooled the department so each researcher was assigned to a specific production team.
I lobbied hard to be put on the Book Club team, but that position went to a brown-nosing asshat from some southern state who wore her accent like a badge and didn't know what they meant when they asked her to create a list of "classic literature." She came to me and asked, "I honestly just don't understand what they mean by 'classic.' What makes a book a 'classic?'" I ended up putting the list together for her and, of course, she got the credit.
Long story short(ish) I ended up being uncerimoniously fired for "not having the Harpo Spirit." Something to do with me not wanting to stick around and work late hours and on the weekends for the production team who seemed to only want me around to order pizzas, get them coffees, and pick up dry cleaning.
As it was the very first time anyone had ever fired me from anything, I was heartbroken. But as the years have gone on, I realize I am much better off and much saner and probably less addicted to drugs and drinking than I would be if I still worked there. I was super pissed when she started taking everyone and their families on vacations, though. All I ever got was one lousy Christmas party and a Tina Turner concert out of her... Oh, and all that free stuff... Right.
And also, yeah, Oprah is just not right. I ran into her once on my way to get coffee one early morning and it was just me, her and her dog walker in the stairwell. I politely said "Good Morning, Ms. Winfrey, I hope you had a good break," and she couldn't be bothered to acknowledge my existence (which really didn't surprise me as her security goons used to have to clear the hallways any time she was going anywhere because she didn't ever want to come into contact with any of us).

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