By the time The Oprah Winfrey Show began airing in national syndication on September 8, 1986—30 years ago next month—its driven and charismatic host was already a bona fide celebrity in Chicago and a rising star nationally. From her base at 190 North State Street, home of WLS-TV, the 32-year-old Baltimore transplant had propelled the station’s half-hour morning gabfest, A.M. Chicago (which was eventually renamed and expanded to an hour), from little watched when she took over in 1984 to top rated, besting her well-established chief competitor, Phil Donahue, in his home market. Winfrey had also garnered an Oscar nomination for her supporting role as the fiery Sofia in Steven Spielberg’s 1985 film The Color Purple, chatted it up with David Letterman on Late Night and Joan Rivers on The Tonight Show, and hosted Saturday Night Live.

Despite those accomplishments and her public displays of self-confidence—“I was like a hit album waiting to be released,” Winfrey told the Chicago Tribune in December 1985, four months after announcing a syndication partnership with New York–based King World Productions—success outside of Chicago was far from guaranteed.

Three decades after it debuted in a record 138 markets reaching 92 percent of America’s TV-viewing audience, Winfrey and key insiders share memories of The Oprah Winfrey Show’s first syndicated season—and the start of something unforeseeably big.

Robert Feder, TV and radio columnist (then with the Chicago Sun-Times)

Oprah [on her local show] had gone to No. 1 in Chicago after a month on the air. But there was still the question: What happens around the rest of the country with this unknown African American woman going up against the giant Phil Donahue?

Chris Tardio, Producer

I don’t think any of us ever assumed it wasn’t going to work, which isn’t to suggest that we weren’t under a lot of pressure and it wasn’t really intense and we didn’t want to do great. I do believe that every one of us understood that Oprah was a very special talent: incredibly bright, naturally inquisitive, as comfortable in front of a camera as not. It was just a matter of how big will it be?

Jeff Jacobs, Harpo Entertainment Group president and chief operating officer

When I expressed the thought that I hoped the rest of the country would love The Oprah Show as much as Chicago did, Oprah said, “People are the same everywhere—same feelings and emotions. If they like it in Chicago, they will like it everywhere.”

Debbie DiMaio, Executive producer

We had been in daily live rehearsal [doing the local show], so our only challenge going into [the national debut] was what to do on the first day.

Tardio

Getting a guest for the first show was a real trick. We reached out to every hot celebrity at the time you could imagine, and no one would do it, because no one really knew what we were doing or who Oprah was.

Alice McGee, Publicist and vice president of communications

Oprah gave Debbie license to call whoever she wanted. Debbie was begging, we were begging. Mike Ditka. Don Johnson. He was someone they really put the full-court press on.

Ellen Rakieten, Producer

We sent Don Johnson a mink teddy bear and rhinestone sunglasses. [Johnson declined.]

Tardio

Once we sort of went through the Rolodex of celebrities and nobody would do the first show, we said, “All right, what have we done [locally] that was really successful? Let’s re-create that for the national audience.” And that’s what we did.

DiMaio

I was going through topics with a longtime friend of Oprah’s, Quincy Jones, and I remember him shaking his head and looking at me and saying, “Baby, you are Pygmy stretchin’.” Like, “You’re trying to make something out of nothing here. You are in trouble.”

The subject of the first show: “How to Marry the Man/Woman of Your Choice.”

Oprah Winfrey

[From a journal entry she wrote at midnight before the show’s debut] I keep wondering how my life will change, if it will change—what all this means. Why have I been so blessed? Maybe going national was to help me realize that I have important work, or that this work is important.

On September 8, 1986, Winfrey stood amid her studio audience of 75 and excitedly proclaimed, “I’m Oprah Winfrey, and welcome to the very first national Oprah Winfrey Show!” Broadcast live in Chicago from 9 to 10 a.m., it was reaired across the country later that day.

Winfrey

[On her debut show] I have hives under my armpits.

DiMaio

We had a big party in Chicago [after the first show] in Grant Park in a big tent, and after the party I got in the limo with Oprah and I turned to her and said, “OK, we gotta stop right here. Because this is that moment where everything changes. We’ve got to be really present in this moment.” It’s like Bruce Springsteen’s “Glory Days”: they’ll pass you by in the blink of an eye.

The rest of week 1 was a smorgasbord: “Feuding Families,” “Aryan Nations,” “Sexually Abused by Doctors,” and “How Fat Affects Marriages”—much more sensational subjects than the New Agey, self-empowerment topics Winfrey would gravitate toward in later years.

Dianne Hudson, Producer

One of Oprah’s big things was, “Just run your race. Don’t look at the other horses in the race.” So we were in our zone and we really weren’t watching [to see], “What did Donahue do today? Let’s do that.”

McGee

No matter what was going on in your personal life, everybody [on staff] was all in for that hour. We were so attuned—even with our menstrual cycles. Sometimes we didn’t even talk. We didn’t need to talk. We just all knew what to do.

Phil Donahue, Talk show host

We continued to enjoy very good business, but it’s certainly true that Oprah started to make a lot of noise. I don’t recall being bright enough to see how powerful she could potentially become.

The Oprah Winfrey Show shot to No. 1 in New York City, Los Angeles, Philadelphia, and San Francisco during its first four weeks, and the wins kept coming. By October, in its hometown of Chicago alone, the program was seen by about 312,000 households—43 percent of those using a television from 9 to 10 a.m. At WLS, some say, there was envy in the air.

Tardio

Oprah had been treated like a stepsister from the time she arrived [at WLS] and started to build her morning audience. The news anchors were really the broadcast stars, as they are at any local station. But because our show was pretty close to an instant hit in syndication, that just elevated Oprah way above local news talent. When her star power eclipsed them, she and we were treated as the “Oprah clique” that didn’t mingle and were too big for our collective britches.

Lesia Minor, Production associate

When I would go over [to WLS] to edit, they were just—I don’t want to say nasty, but they were not as helpful as I think they should have been. Or some of the people would have a little attitude if you were going up in the elevator to the show.

It didn’t help matters that WLS could not profit from the show’s syndication because of restrictive federal regulations. The station was allowed to recoup only its production costs, around $4 million per season.

Joe Ahern, WLS general manager

It was extraordinary at the time that we couldn’t share in the profits. King World was the one really making terrific profits.

Tardio

Now that King World was involved as a syndicator, we not only had a master at the local ABC station, we had a master on a national level, which suddenly makes you aware that there are a lot of eyes on this. They didn’t meddle and they were really supportive, but we certainly felt the pressure that we were playing a game in a much, much bigger arena than we were before.

Tim Bennett, WLS program director

King World was so stunned in a most positive way at the success. Roger [King, the CEO] would just call up and say, “Is there anything I can do? Do you need money for anything?” He was tripping over himself out of excitement, because he had never seen, nor had any of us ever seen, anything like this.

The show’s topics—be it celibacy in the Catholic Church or miserable marriages—often connected with viewers (in particular, a core demographic of women ages 18 to 49) on a personal, even visceral, level. And while critics allowed, if only grudgingly, that Winfrey’s raw and real approach was engagingly unique, several denounced what they perceived as the show’s frequently tabloidish tone. A few days in, the Los Angeles Times’ Howard Rosenberg dismissed Winfrey’s program as “little more than low-brow Donahue,” with “feuding families sandwiched between an hour of male-hunting and an hour of Jew hunting, all in the name of Nielsen hunting.” TV Guide described the show as “so American it burns your eyes.” Indeed, the staff’s internal mantra to “Uplift, inform, enlighten, and entertain” wasn’t always fully adhered to. But as Winfrey would profess in a later season, after a show about sex addiction, “I say it’s OK to titillate if in the process you help someone.”

Winfrey

What I have always felt was that the show was a ministry to be used for good. It was never just a show for me. This was a show to help people know that they’re not alone. My goal from the beginning was to dissect the human dysfunction in such a way that people could see themselves and do better.

Rakieten

There were [topics] that we decided not to do because once we got involved in them, it just seemed like we were going to give somebody a platform for something that wasn’t good. After we did something with a white supremacist group [in episode 3], we realized we were never going to do that again. They weren’t coming to be part of something, to open eyes and [create] an understanding. And we realized early on, after a few experiences, that we didn’t want to blindside or ambush anybody, unless it was like, “Here’s your dream wedding.”

DiMaio

We felt we were designing the show to inspire people and invoke some sort of positive change in their lives. We also knew that in order for the show to be authentic and ring true to viewers, we would only do topics that Oprah herself was personally interested in. So those were kind of our parameters, and it was pretty easy to make decisions based on that.

Winfrey

When we’d have our meetings, [we’d ask], “What were people talking about at the hairdresser this week? What are people talking about in the restaurants you’re in? What are people talking about in your family?” That’s where we built the shows, right straight up out of our lives.

McGee

We were sitting around, and Dianne Hudson was telling us her [childbirth] story, and from that we did probably one of our most irresponsible shows [“Labor Horror Stories”]. Dianne had a really rough labor and thought bones were breaking. Every emergency room was calling us, saying, “How could you do this?”

Hudson

I was the only one on staff at the time who’d delivered a baby. I felt that the actual experience was often glamorized. So we just did a show where women shared their real-life experiences without trying to be politically correct about it. Maybe Alice got some calls from hospitals. I don’t know. I know we got great feedback from women viewers who appreciated the honest talk about a common experience.

Winfrey

We were flying by the seat of our pantyhose. We were doing shows that came out of a really pure space. We were doing what we thought was interesting and would connect to the audience. We were completely, absolutely so naive about the business of the business. The only strategy was, “What do we think will work?” And every single thing, I gave a gut check to. And that’s how we operated, straight out of the gut.

DiMaio

We were single women, for the most part, projecting ourselves into the minds of married women with children in the suburbs who were, at that time in the afternoon, doing housework or taking care of their kids or making dinner. Television had a tendency to be white noise in the background. Oprah was cutting through that with personal truth.

Hudson

We’d come up with these topics that were impossible to book. We’d announce [on the air], “If your husband is abusing you and it’s happening right now, call us and we want to talk about it on the Oprah Show.” So we’re looking for somebody who just got beat up last night and needs a way out, needs help, and is scared to death. The phones would ring off the hook. It was of the moment and it was real.

McGee

We were so trusted by our viewers. I swear to God, one time this [female caller] said, “I just don’t know what play set to buy for my children.” Seriously? We also became a suicide and sexual abuse hotline in some ways. [Even before we went national], it was like, “Please hold. Please hold.”

DiMaio

A lot of things and people had to come together to make this show successful and national, but there’s one group that always kind of gets overlooked, and that is the Chicago audience. At the end of every show, we would make an announcement on what [topics] we were doing. “Are you thinking about leaving your husband?” “Is your weight causing you problems?” And Chicago women picked up the phones and called us. We really couldn’t have done it without them.

In an era before email and social media, letters from viewers came flowing in like never before. Winfrey and her colleagues, swamped by daily production demands, handled the influx as best they could.

Winfrey

Oh my God, it was crazy. We couldn’t keep up with it. And in the beginning, I felt like we had to answer every letter, we had to respond to every person, we had to answer every question.

Minor

She received at least 1,100 letters a week. Mail was just flooding in. Oprah liked to know what people were saying. And she always liked to help someone in need.

McGee

I was on the frontline getting the feedback. Reading the letters and seeing the way Oprah struck a chord with people, I felt, This is more than a show.

Minor

Some of the letters, especially those [from women] being physically abused and they just didn’t know what to do—those were heartbreaking.

Rakieten

I remember the first time I got a letter from somebody based on a show we did [“People Who Kill Accidentally”]. She said it literally was the day she was going to kill herself, and she decided not to.

As the season went on, producers continued to pack the schedule with episodes that explored a variety of topics: obsessive love, terminal illness, bisexuality, in-law tension, and women in love with criminals. The staff planned the shows out of modest offices at WLS.

Hudson

We were in one big room, and it wasn’t all that big. We had one person booking the audience and one person who answered the phones. Debbie had her own little separate section, Oprah had an office in the back, and that was it.

Tardio

We worked insane hours, and we were really single-minded about it. It was our lives. We ate it, breathed it, slept it. We worked weekends. We worked nights. None of us had a life outside of that.

Bennett

When I’d leave at six or seven o’clock, [Oprah’s staff members] were still there. And a few times when I had a [late] function downtown, I’d come back to pick up some things and they were there at 10 o’clock. It was nonstop.

McGee

I know a lot of people at the time were like, “It’s a cult.” And it was in some ways, because we were of one mindset about the quality of work that we did.

Winfrey

Immediately it became more than just a show for them.

McGee

The cult thing didn’t originate at WLS, but likely in the Chicago media, who [saw] how fiercely protective and tightlipped we were about Oprah and the work we were doing, [knowing] that whatever we said or did in public could and would turn up in the next day’s gossip column.

Rakieten

We were all up in each other’s lives and what was going on. We would go into Oprah’s little makeup area and put on her makeup and take her earrings and whatever was in there, and we’d go out at night. Going to work there felt like going home.

McGee

Oprah gave a lot to us, but she expected a lot, too. She had really high standards. It was her ass on the line every day, and we felt that. It was palpable. She wasn’t nice. [She was] kind, openhearted. She’s not going to say, “That’s a great show” unless it’s a great show. And you’d hear about it if it wasn’t. So you wanted to deliver the goods for her.

DiMaio

Our meetings were very freewheeling. Each producer would come with a list of ideas, a pile of “expert” books, and pitch their ideas to me. We’d often take a kernel of one idea and brainstorm until we came up with a topic. We all sat in a small room, with six or seven desks facing each other. One wall had a giant dry erase board with the show topic calendar. Under that was a ledge that usually held a huge bowl of guacamole and chips and, on Fridays, a pitcher of margaritas. We shared personal stories and opinions about every human failing on the planet, and with that came compassion for each other and the audience.

McGee

If we could talk about something for a half hour, it had to be a show.

When November sweeps ended, the show was, as Feder wrote in the Sun-Times, “the top-ranked program in its time period in every one of the nation’s 10 largest cities.” King World was downright giddy. “Never has any first-run, syndicated show of any kind opened so strongly right out of the gate,” the company’s vice president of research breathlessly proclaimed. It was connecting like never before, and so was Winfrey, who cried with her audience and guests, giggled with them and at herself, and shared their anger and outrage. “I understand myself through your show,” wrote one viewer. “Sometimes I find myself laughing, sometimes cheering, and sometimes sitting in wide-eyed wonderment at the vastness of human love and compassion.” Although Winfrey had never been more beloved, she was also more of a target for those aiming to take her down. In December 1986, in a magazine story mock-ominously titled “It Came from Chicago,” journalist Bill Zehme, 28 at the time, repeatedly skewered his mark with the linguistic equivalent of a blade just off the whetstone. Originally written with Winfrey’s cooperation for Vanity Fair before being rejected there and migrating to a fledgling satirical monthly called Spy, his snappy and sarcastic profile savaged everything from Winfrey’s unabashed materialism (“I say minks were born to die!”) and aspiration to be “the richest black woman in America” to her ample girth and soaring grandiosity.

In the story, Winfrey is quoted as saying: “I believe that I have a higher calling. What I do goes beyond the realm of everyday parameters. I am profoundly effective. The response I get on the street—I mean, Joan Lunden [of ABC’s Good Morning America] doesn’t get that, and I know it. I know people really, really love me, love me, love me. A bonding of the human spirit takes place. Being able to lift a whole consciousness—that’s what I do.”

McGee

Oprah read the Spy article in the office. The WLS PR woman brought in a copy. And Oprah’s reaction—ours too—was that it was just so over the top we did not discuss it. Minutes after reading, Oprah wrote “I forgive you” on her personal stationery and asked me to mail it to Spy, which I did the same day. Spy published those three words in their [March 1987] edition under letters from readers. Generally speaking, Oprah didn’t get caught up in negative press and wouldn’t change her MO based on observations from [critics] eager to find fault with what we were doing.

Winfrey

[I was] literally always operating from my gut. I wasn’t thinking about what other people were going to think, particularly in those early years. As I became fodder for the tabloids, I was more conscious of what I said and how I said it. But the first year was full-on uncensored.

Bill Zehme, Journalist

I’m embarrassed by the piece entirely at this point. But I couldn’t help but make fun of the fact that she was very self-messianic. I’d never seen anything like it in my life. I’d never heard anyone talk like this. It was shocking. She would say things like “Money falls off of me” and “I was put here for a deeper reason.” The woman was in her 30s and you’re thinking, What the hell is going on here? This is Norma Desmond going haywire early, before the talkies. After it was killed by Vanity Fair—I think they didn’t want to go after, or even poke fun at, a woman of color at a moment when maybe that wasn’t the best thing to be doing—Spy desperately wanted to see it. And they really stepped up the bad adjectives. It was sharp when I turned it in, and they made it into a stiletto. When it came out, I got a note in the mail from Oprah on her stationery in a purple envelope: “Dear Bill, I forgive you. Oprah.” I can’t remember if I sent her flowers [before the note came] or afterwards. But people in the local media really liked the piece. There was a certain amount of giddiness afoot in Chicago about it that I did not embrace. The thing is, everything she said about what she was going to be—it was all true.

As her own fame grew, Winfrey began collecting more famous friends, and celebrities were increasingly willing to appear on her show. Throughout the second half of the season, having already scored a handful of well-known guests such as Lionel Richie, Barbara Walters, and Liberace (in what would be his final television appearance), Winfrey’s producers were able to book the even more famous likes of Burt Reynolds, Mel Gibson, Arnold Schwarzenegger, and Eddie Murphy.

McGee

Eddie Murphy wanted to fly first class. He wanted an entourage. He was young and successful. He wanted to party at the Pump Room, dammit! He wanted blondes. And Oprah used her own money to make that happen.

Minor

It was a big party and there were lots of women there. His handlers would just point out girls that Eddie wanted to come up to his room [at the Ambassador East]. One of my friends said, “I’m going up to his room.” I said, “Oh, no you’re not.”

Stars, though, made up only a small fraction of the guests. And while sensationalistic fare continued to pepper the roster (alien abductions, sex slaves, witches), topics occasionally turned dark. Sexual abuse was one of them. On her local program, in 1985, Oprah had revealed that she was abused as a child by relatives, as well as her mother’s boyfriend. She repeated a version of the story on national television during a brief taped intro on November 10, 1986, sparking a large uptick in letters and calls from survivors, and thereafter she devoted a number of episodes to the subject of sexually abused children and adults.

Race, too, was an occasional topic. As the country’s only African American female host of a national talk show, Winfrey was judged harshly by some in the black community for seeming too cozy with white America and for failing to sufficiently highlight the struggles of her own people. It wasn’t a hollow argument. At the end of season 1, only seven of more than 200 episodes had centered on so-called black issues.

Feder

The biggest [local] television story in 1986 wasn’t Oprah Winfrey. The biggest story on my beat was the boycott that Jesse Jackson was staging at WBBM-TV by Operation PUSH because the station had demoted its only black anchorman, Harry Porterfield. The city and television were so racially divided, and there was great sensitivity.

Hudson

[Oprah and I] are the same age. We were born in the ’50s in the South, so we came from segregation, from Jim Crow. We went to college during affirmative action time. When I came to the show [in the late summer of 1986], I was the only African American producer on the staff. There was definitely a responsibility we felt, not only to be successful but also to represent.

Winfrey

[There was] lots of pressure from the black community, so much so that I had a conversation with Quincy Jones, Maya Angelou, and Sidney Poitier about it. And Sidney Poitier said something to me that sort of became an imprint: “People expect a lot when you’re carrying their dreams.” I had black people saying to me, “Why are you always in the audience hugging white people? You don’t do enough shows about black people. You don’t do enough things to help black people.” And it was hurtful to me because I understood that, first of all, just the fact that I was there, hosting the show, was a step forward. And also, I understood that what you’re really trying to do is open up the heart space. I didn’t have the language for it, but you’re trying to get people to see what Maya Angelou articulated for me: that we are all more alike than we are different.

Roosevelt Cartwright, Winfrey’s makeup artist

I’m from the streets, and I’d hear what the black community was saying—that she catered to the white people. It hurt her, because she really didn’t. She had a show, and then she did what she wanted to do in the community. And she helped a lot of black people, but people didn’t see that. She’d read her [viewer] mail and say, “Roosevelt, go to these people’s house. Before you give them any money [provided by Winfrey], see what you think.” So I went. If I saw anything out of the ordinary [like drugs], I’d say, “I’m just dropping by.” I would not give them money. Instead, I’d go take them grocery shopping or turn their [electricity] on.

Winfrey

I remember a moment that impacted me for a long time, and I know had an impact on the audience. We were doing a show on parenting, and we had footage of a black father putting his two little girls to bed and reading to [them]. I knew that moment was more powerful than all the shows you could do on African American parenting because you got to see, “This father feels about his children the same way I do.” And that’s how you break down the walls of prejudice and racism, [by seeing other] people as yourself.

During February sweeps in 1987, at the outset of Black History Month, Winfrey and a small crew flew to Cumming, Georgia, in Forsyth County, about 40 miles north of Atlanta, to shoot a live show. For 75 years, ever since hundreds of blacks were forced from the city after rape and murder allegations were brought against three young black men there in 1912, Cumming had stayed all white, and most of its residents remained staunchly against integration. Roughly two weeks prior to the taping, Hosea Williams, an Atlanta city councilman and civil rights activist, had led 12,000 to 20,000 marchers in a protest in Cumming against Forsyth’s history of segregation. According to a New York Times report, they were met by “a stern-faced force of 2,300 guardsmen and police officers, [and] a group of hundreds if not thousands of white, mainly young, rural men and women, repeatedly shouting, ‘N—-r, go home!’ ”

Winfrey

I couldn’t believe there was still this all-white town. And we started talking about what would happen if I went to an all-white town.

Rakieten

We were really going into that situation because we wanted to know what was going on. We weren’t going in with any big prejudgment.

DiMaio

I went in advance to scout a location. I think word got out that I was there, and someone called me at my hotel room and said they were going to kill me. I was by myself, and I remember pushing a dresser in front of the door—not thinking I should call hotel security or anything—and just hoping for the best.

Bennett

From a production point of view, it was an anxious couple of days, because you didn’t know how some people would react.

Winfrey

My goal was to put ignorance on its most blatant display so that people could see for themselves how ridiculous it is.

Cartwright

The white people loved Oprah in Forsyth. I remember this woman stood up [during the show] and told Oprah [paraphrasing], “Oprah, you’re no n—-r. But the rest of them are n—-rs and we don’t want them in our county.” I moved to Atlanta later and I go to Forsyth now, and it’s totally different.

DiMaio

We did that show in a restaurant. I looked on the monitor and saw Hosea Williams literally marching up the hill. [He had returned midshow to make a stand against what he described as Winfrey’s “totally unbalanced” approach of featuring only residents, all white.] So there was the threat of violence in the air between [white] protesters and Hosea Williams. It was about to go south when the show ended. Coming outside with Oprah was almost like going from a dark room to sunlight. There were dozens and dozens of reporters there and cameras flashing and people hollering. It was just amazing. Astounding. It was such a clear example of the power that show had.

When the episode aired in 145 markets, it earned its highest national ratings yet and got lots of attention in the media. By the end of February sweeps, The Oprah Winfrey Show was the No. 1 syndicated talk show in America and third out of 400 syndicated programs overall, behind only Wheel of Fortune and Jeopardy! It had fast become such a force that it even merited mention the following month in a Donahue parody on Saturday Night Live.

On September 7, 1987, after 228 episodes, The Oprah Winfrey Show’s inaugural syndicated season wrapped, maintaining its top slot among syndicated talk shows. Winfrey herself won big, too, earning, by her own estimate, between $11 million and $12 million from her share of the syndication profits—a sliver of the gargantuan paydays to come. The show would go on to earn three statues at the Daytime Emmy Awards that year—a ceremony hosted by Winfrey—including for outstanding talk or service show and one for Winfrey as host. Over the years, forty-four more Emmys would follow.

A couple of days after the season’s end, Winfrey, her staff, and hundreds of well-wishers celebrated with a splashy victory bash on Navy Pier, dubbed OprahFest. Few of the invited celebrities came, the Tribune noted, but Winfrey’s The Color Purple costars Danny Glover and Akosua Busia were on hand. So were Winfrey’s father, Vernon, her beau Stedman Graham, and several people—including Roger King, Jeff Jacobs, and Tim Bennett—who’d played key roles in her rise. Effusive tributes to and from the woman of the hour abounded. It had, after all, been an extraordinarily auspicious start, one that kicked off a 25-season run that ultimately drew billions of viewers in 145 countries and generated billions of dollars. During that seminal first year, though, not even a lofty prognosticator like Winfrey could have predicted how far it would go.