#25 (tie): Confronting a Tabloid Snitch (November 16, 1992)
A week after announcing her blockbuster engagement to Stedman, Oprah spoke with Al Schweitzer, a private eye and admitted briber, who said he once sold Oprah's personal phone number to a tabloid.
#25 (tie): Follow-Up Show 1991 (November 25, 1991)
From a mooching son to a woman who defended herself against a potential rapist to couples fixing their relationships, Oprah looked back at some of the most unforgettable moments of her sixth season.
#24: Friend Makeovers and Fashion (November 8, 1988)
In 1988, Oprah convinced Gayle's mom, Peggy, to chop her long locks and reach the hair-raising height of '80s fashion.
#23: Inside the Life of an Obese Person (February 7, 1994)
This was the first of many times The Oprah Show
checked in on Stacey Halprin
—who would later go on to lose more than 350 pounds and inspire others to take control of their weight loss.
#22: How to Find Loved Ones, Hated Ones and People Who Owe You Money (February 11, 1994)
In 1994, 50 people in Oprah's audience learned the techniques of private detectives to find people missing in their lives.
#21: Denying My Race (February 8, 1994)
Shirlee Haizlip, author of the book The Sweeter the Juice, told how members of her biracial family had at different times chosen to identify, or "pass," as different races.
#20: Only Good News (November 5, 1993)
This was one of Oprah's favorite episodes ever—an hour of wall-to-wall, grin-inducing good news. Oprah spread the love by giving some hard-working neighbors the day off, babysitting for a deserving couple, hiring a job applicant at Harpo and even giving away a puppy to a boy who had always wanted a dog!
#19: Rodney King Verdict: Anger and Aftermath (May 5, 1992)
In 1991, Rodney King, a black man from Los Angeles, was pulled over by police after a high-speed chase. An amateur video that was seen around the world showed LAPD officers hitting King more than 50 times with a baton and kicking him six times before handcuffing and arresting him. After a trial on police brutality charges ended with a not-guilty verdict for the officers, some black residents of L.A. rioted and looted.
In 1992, everyone in America had an opinion about the verdict and the riots—and Oprah was in Los Angeles to hear them out.
#18: People Shed Their Disguises (February 21, 1994)
In this 1994 show, a man with a 20-year-old beard found himself in a close shave, a man said "ta-ta" to his toupee, a makeup addict went in for an intervention, and a woman who wore wigs for a quarter-century was convinced to go "topless"!
#17: Forsyth County, Georgia (February 9, 1987)
Oprah earned her reputation as someone who will talk to anyone
when she traveled south to tape a show on race with the residents of Forsyth County, Georgia, in 1987. Then known as a hotbed of racism, Forsyth County hadn't had a single black resident since before World War I. Tensions ran high and calls for understanding were few.
Read what happened when The Oprah Show returned to Forsyth County 24 years later
#16: I Hate Your Interracial Relationship (February 17, 1992)
Loving v. Virginia, the landmark Supreme Court case that legalized interracial marriage, turned 25 years old in 1992. But these marriages, especially between whites and blacks, were still taboo throughout America at the time of this highly rated show.
#15: Elizabeth Taylor (March 4, 1992)
Oprah's first interview in 1988 with Elizabeth Taylor
was legendary alright—legendarily bad! Right before the interview Liz announced she wouldn't talk about her famous relationships, and gave short answers to all of Oprah's questions. Oprah later found out Liz was in excruciating back and hip pain at the time.
In their second interview four years later, the queen of Hollywood was finally ready to open up about her marriage (her eighth) to construction worker Larry Fortensky, her close friendship with Michael Jackson, her time in rehab and her tireless work as an AIDS activist.
#14: The Other Side of the Betty Broderick Story (November 3, 1992)
Seven months after her interview with Betty Broderick, the woman convicted of murdering her husband and his second wife, Oprah revisited the story and gave a voice to the youngest victims: Kim and Dan, the Broderick children.
#13: Reunited with Your First Love (February 11, 1992)
Meet the ones who got away! In 1992, Oprah and Gayle took a trip down memory lane and checked in with their high school sweethearts.
#12: Meet Erica Kane and All Her Men (February 18, 1991)
In 1991, Susan Lucci—Erica Kane on All My Children
—appeared with the eight men who've played her TV husbands.
Watch what happened when Susan reunited with them again in 2011.
#11: When the Wife Meets the Other Woman (February 20, 1989)
This episode featuring a classic daytime TV topic aired on the Monday after one of Oprah's all-time most-memorable shows: Alaskan bachelors who were looking for brides.
#10: How Fame Affects a Relationship (February 2, 1989)
When Oprah needed a guest to talk about how paparazzi and tabloid headlines can affect a relationship, she didn't have to look far for an expert. On this 1989 show, she and Stedman opened up about their life in the spotlight, and Stedman even answered a question—asked, literally, by everyone in the audience—about when he was going to marry Oprah. "I love her and she loves me. She's my woman and I'm her man," he said. "We will announce properly when we're going to get married when we decide we're going to get married, and not before."
#9: Oprah's Weight Loss Show (November 22, 1993)
When Oprah wheeled out that red wagon of fat in 1988, she thought her war with weight was over, but it had only just begun. In this 1993 show, Oprah read from her personal journals about the humiliation of getting up to 226 pounds, and then announced the big change in her life: personal trainer Bob Greene! In Bob's first show, he demonstrated why confronting the emotional element of weight loss is just as important as nutrition and exercise.
#8: Fifth Anniversary Show (September 9, 1991)
In this clip show, Oprah looked back at the most unforgettable moments of her first five years on the air—including the wagon of fat
, the woman with 92 personalities
, Robin Williams, and the trip to Forsyth County, Georgia
. "Some of the best times of my life have been spent right here on this show," she said.
#7: Why I Love Older Women (February 15, 1993)
Think the term "cougars" was invented for Ashton and Demi? Think again! Oprah tackled the topic of older women who date younger men back in 1993. In the show—which included a phone call with Cher—a guest named Vinnie had the quote of the day: "It's the difference between riding in a Volkswagen and a Cadillac," he said. "If you want to ride in a Volkswagen, go ahead. If you want the Cadillac, go for an older woman."
#6: The Home Alone Controversy (January 11, 1993)
In the 1990 comic hit Home Alone, 8-year-old Macaulay Culkin is accidentally left behind as his family heads off on a Christmas vacation—and hilarity ensues. In a true case from 1993, parents David and Sharon Schoo left their daughters Nicole, 9, and Diana, 4, alone while they took a Christmas vacation to Mexico. When David and Sharon landed, they were arrested on charges of child abandonment, endangerment and cruelty.
Using this case as a springboard for discussion, Oprah interviewed parents about whether it is ever acceptable to leave young children unattended at home.
#5: Oprah Makeovers (February 2, 1993)
While lucky staffers from The Oprah Show and Entertainment Tonight got style makeovers, the big news came at the beginning of this show when Oprah confronted tabloid headlines about her alleged wedding plans and even reports of a secret pregnancy! "As things come to life and as we start making plans, I'll let you know," Oprah said. "You don't have to read the trash, okay?"
#4: I Killed My Ex and His Wife: Betty Broderick (March 2, 1992)
In her first interview after being convicted in the murder her ex-husband and his second wife, Betty Broderick opened up to Oprah about why she did it. In 1992, Betty's story was later turned into a two-part made-for-TV movie starring Meredith Baxter
#3: Michael Jackson (February 10, 1993)
Oprah's groundbreaking 1993 prime-time interview with Michael Jackson at his Neverland Ranch provided her with two of her highest-rated shows of all time.
On the afternoon before Oprah's prime-time interview with Michael Jackson, The Oprah Show was all about the King of Pop. Oprah interviewed Michael's biggest fans and celebrity friends Gladys Knight, Smokey Robinson and Iman. Oprah even revealed the time she tried to do a Michael Jackson impersonation on A.M. Chicago in 1984!
#2: Celebrity Hall of Fame (February 11, 1993)
On the day after the interview, The Oprah Show ran a montage of highlights from Oprah's biggest celebrity interviews to date—Bill Cosby, Elizabeth Taylor, Bette Midler, Tom Cruise, Arsenio Hall and more.
#1: Diet Dreams Come True (November 15, 1988)
In what became a milestone moment in pop culture history, Oprah rolled out a little red wagon loaded with 67 pounds of fat
—equal to her weight loss success at the time.