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15 Most Expensive Gifts Oprah Gave Her Friends


15 Most Expensive Gifts Oprah Gave Her Friends

Everybody knows Oprah from her popular and world-renowned talk show. But now that she’s retired from hosting and spending every single day of the week in front of the camera, she has taken to the sidelines –  but only in that respect. Oprah is still pretty much active and influential as ever. She was just recently in a film called A Wrinkle In Time with Reese Witherspoon and Mindy Kaling, and is busy everyday running her network, OWN, or the Oprah Winfrey Network. She is also not taking a backseat in terms of being in the background, or off-camera, as owner, founder, and CEO of Harpo Productions.

Oprah Winfrey is reported to have a net worth of 3 billion dollars. She is one of the richest women in the world today. We all know her history, coming from poor beginnings, with nothing when she was born, no regular spoon, let alone a silver one. She strived her way to the top, made a name through broadcasting news and eventually moving to Chicago to have her own show. The rest, as they say, is history. Oprah is known to have a very generous, and sometimes, ridiculously extravagant, heart. Here are just 15 examples of how expensive her gifts to people can be.

15. Gayle King’s best Oprah gift ever

If anyone’s been watching the CBS network every morning, chances are you have seen Gayle King. She is the co-anchor of the morning show CBS This Morning, and been for the sixth year now. She became a member of the show back in 2012, but it had been a series of ups and downs for Gayle before she got the CBS gig. She started in news and was in this medium in the state of Connecticut for 18 long years. She was part of an NBC talk show and her own one, which were both cancelled. She was rumored to replace certain big names on the show The View, but it never took.

But what Gayle King is really known for is being Oprah’s best friend. She’s spent countless moments with Oprah, both typical, regular days, and special, important occasions. Oprah has showered her with everything a best friend could get from her best friend, but Gayle shared the best gift she has ever gotten from Oprah. She said that the best gift she got from her was a live-in nanny for her second baby. It was more on the circumstance, the timing and the importance of the gift. At the time she could not really afford a permanent nanny, and her best friend just solved that problem for her.

14. Baby showers and college scholarships

Once in a while, Oprah, in her show, would call upon a certain group of people, tell the world their story a little bit, and give them something that they will cherish forever. In 2006, she gave the audience of her show $1,000, a handheld camera, and a challenge to pay it forward and record it. That’s something no other show has ever done, it’s the mantra of Oprah’s show. At the beginning of the same year, Oprah held a National High School Essay Contest. From the 50-some thousand who sent theirs, 50 students were chosen. These kids were given a $10,000 college scholarship.

Perhaps one of the biggest gift-giving event the show ever had was the baby shower she had in 2004. Together with Cindy Crawford, she was on-site with Oprah, and other celebrities via Skype, they made almost 700 moms-to-be blessed and happy. Ben Affleck appeared first, giving the dads Diaper Dudes. Celebrity moms shared the gifts they got in their own baby showers. Cindy’s gifts were soft carriers and ExerSaucers. Heather Locklear gave Boppys, a support pillow. Denise Richards gave baby booties, and other celebrities like Sharon Stone, and Elle MacPherson, gave gifts of their own. There were also singing performances from Martina McBride and Kenny Chesney.

13. Lucky Mindy Kaling

Mindy Kaling is popularly known for her TV role as Kelly Kapoor in the NBC show The Office. She acted, wrote, directed and also had her own show called The Mindy Project. She was in two big films this year, Ocean’s 8 with Sandra Bullock, Cate Blanchett and Anne Hathaway. The other is A Wrinkle In Time with Reese Witherspoon and of course, Oprah Winfrey. At a movie press junket, oprah accidentally announced that Mindy was pregnant even before Mindy announced it anywhere or to anyone else. This story would be totally different if a different person spoiled it for Mindy.

Oprah made it up to Mindy though, well, saying she made it up to her is an understatement. She sent a gift for Mindy’s baby, and get this, it had to be delivered by a U-Haul truck. It was nothing, just some books. About a hundred of them, children’s essential classic literature. Oh, and it came with an elegant handcrafted bookcase and dollhouse. Oprah, with all those gifts, was not entirely happy with it and said that she wanted the dollhouse to look like more like the treehouse in their film. Mindy Kaling’s daughter was born on December 15, 2017, her name is Katherine.

12. O Magazine and Oprah’s housekeepers

Working for Oprah Winfrey definitely has its benefits. There are the obvious reasons, she is not just a celebrity, she is The Celebrity. Her net worth is upwards of 3 billion and some of that could just trickle down to us, no one knows. Then there are the other reasons, like a bonus check worth $10,000 or a monthly shopping spree. There was a rumor going around, well Oprah neither denied nor confirmed it, so it is labeled a rumor. But several witness accounts confirm it, and it’s pretty impossible to cover it up or to keep it a secret. They say that every month Oprah takes her housekeepers on a shopping spree, they arrive in a limo, get inside the boutique, Oprah hands her credit card to the cashier, and gives her maids two minutes to get what they want.

Working at O Magazine has its perks, with bonuses and such. During the publication’s 10th anniversary, Oprah gifted a check worth $1,000 to every employee in the company. It didn’t matter whether they were there since the beginning, or just started last week, each and every one got a check. Not just that, they were also gifted an iPad. We’d wait for the magazine’s 20th anniversary, stick around and see what’s in store for the loyal employees.

11. From truffle salt shakers to a trip to Italy

Gayle King’s work is not only as co-host of CBS This Morning, she is also an editor for O, The Oprah Magazine. Gayle was married for 11 years with attorney Bill Bumpus, they had two children, a girl and a boy named Kirby and William. Her time with her children oftentimes cross with her time with her best friend, Oprah. For example, in one birthday celebration Oprah took Gayle and daughter Kirby to Italy. It all started with Mariah Carey.

Mariah Carey went on Oprah’s show and gave Oprah a gift basket with a truffle salt shaker. Truffle is added to salt to give it a taste like no other, cannot be harvested as it grows wild, truffle has to be hunted using sniffing dogs. From then on, Oprah has been raving about how delicious truffle salt is and had it in her bucket list to go truffle hunting one day. This she did, together with Gayle King and her daughter Kirby Bumpus. They went to Italy, in Umbria, and went truffle hunting together. Being Oprah’s best friend has its benefits, she recently had a birthday bash thrown by Oprah and was called The World According To Gayle. Who wouldn’t want a birthday with all the food that you love in one room?

10. From Disney World and the city of brotherly love to Australia

24 years ago, Oprah took her whole audience on a trip to Philadelphia. At the time, this was a big gesture, 1994 was not big on television gimmicks, at least not on talk shows. There were 131 audience members that got to be on a trip with Oprah Winfrey and got to enjoy the City of Brotherly Love. Of course they visited the Liberty Bell and went and climbed Rocky’s famous steps, they also had their fill of the famous Philly cheesesteaks.

Two years later, Oprah was at it again. In celebration of her show’s 10th anniversary, her staff gathered 217 people celebrating their own little, memorable, and important anniversaries. They were all audience members, special people because they all had reasons to be there, and Oprah whisked them off to Orlando. Their destination, Disney World, the mother of all Disney Worlds.

At the beginning of her show’s 25th season, Oprah had something big planned. It had to be bigger than Disney World, it had to be further than Philadelphia. This is it, the last time they get to treat random people to a trip they will cherish forever. This time around they gathered what they called Ultimate Viewers and took them all to Australia. It was eight days in the Land Down Under, enjoy your time there, mate!

9. Barbara Winfrey’s gift

Vernon Winfrey was the father Oprah looked up to. But she spent most of her young years with her mother and grandmother, her father was not there for her until later in her life. Except for a short while when she was 8 years old, when she lived with her father for a time in Nashville, Tennessee, she grew up around her mother or grandmother. But ever since then, life with her father was not always good. But now that she has made a name for herself, things and circumstances have changed. Oprah’s mother was Vernita Lee, Barbara Winfrey was actually a different woman, not related to Oprah, that her father married when Oprah was 40 years old.

Their marriage did not last, Vernon and Barbara, but in the 14 years they were together, Oprah was able to give them a gift that was memorable for all of them. It was an 11-day cruise on a private yacht across the Mediterranean. The private rental cost $30 million and Oprah was joined with her partner and her best friend Gayle King. Together with Vernon and Barbara Winfrey, they cruised the Mediterranean on a luxury yacht and dined every day on three-course meals. That’s eleven days like no other. After their divorce, Oprah kind of divorced from Barbara as well, as they did not part in good terms. Maybe it’s because Barbara had to leave the comfy $1.4 million mansion Vernon was living in.

8. Tina Turner and Mariah Carey

Throughout her show, Oprah has given out countless free concert tickets to her audience members, to extraordinary people, to friends who other people wrote to Oprah about, and all the other ways that people get free stuff on the show. There are some that are special, like these two. Tina Turner and Mariah Carey are just two of Oprah’s most favorite people. They are not just perennial performers and singers, the range and the muscles on these women’s throats! They are also lucky to have tickled Oprah’s fancy and be counted as one of her friends. Both women would often guest in Oprah’s show, separately, and promote a concert tour, a show, or an album.

During Tina Turner’s 1997 tour, The Oprah Show tagged along and Oprah brought with her 6 out of 76,000 aspiring women to go on tour with Tina Turner. They arrived in Houston, was given VIP treatment and the time of their lives. It was the whole nine yards: luxury cars, shopping, and front-row tickets to Tina’s concert. In a seemingly regular show, two die-hard Mariah Carey fans asked Oprah when Mariah is guesting in her show again. The nonchalant question led to tickets to see Mariah Carey live in New York. They even got to meet her face to face, and whether it happened or not, these two lucky fans were personally asked by Mariah to join her in her next music video.

7. Mediterranean and Hawaiian holidays

Working for Oprah does not end in shopping sprees and thousand dollar checks, it goes on and will continue to go on as long as Oprah is still breathing. Oprah is making a habit of renting luxury boats and taking people on trips around the world. In 2009, the lucky group of people was her own Oprah Winfrey Show staff. She took her staff on a Mediterranean cruise and rented a nice bar and restaurant. Afterward they went on a 10-day cruise and visited Italy, Greece, and Turkey together with Oprah and their own families, that’s around 1700 people.

On another birthday celebration in 2016, Oprah changed venues and took 40 of her O Magazine staff to Hawaii. It was a vacation, a birthday celebration, and also a commitment to Weight Watchers, as these 40 were handpicked and are expected to participate in a Weight Watchers regimen. No one’s complaining, it’s an all expenses paid trip to Hawaii and a chance to lose weight and be healthier, sounds like a win-win. Both trips were at zero cost to the staff members and Oprah paid for it all. What boss can send their staff on weeks-long vacations? Only Oprah can! What a boss!

6. Princess Fannie and Katrina

Most talk shows recognize and award everyday heroes. These are those people that were never trained to be heroes, never asked to be one, and never ever asked anything in return. One such person was a woman named Fannie. In 2003, Oprah had her as a guest in her show. Not just a regular guest, but she received one of the honors in the show, the title of Princess for a Day, complete with a throne, a tiara, and a scepter. Fannie worked as a housekeeper and nanny and lived in New Orleans. The producers and staff of the show felt she deserved a much-needed break from her everyday routine, and more. They took her off work, sent her on a free vacation to New York City, and replaced her old car (with a busted air conditioner) with a new one. Oprah even gave her maid service for one year. All that because she was a regular hero. When Frannie’s little sister died, she left her three children parentless. Frannie took them in, together with her own children, and did her best to give them the lives they deserved.

Two years after that unforgettable moment for Frannie, Katrina struck and totaled their home. There was nothing left of it but the brick flooring. For 18 months they lived in a trailer parked in front of their property. They just did not have the funds to rebuild their home. Nate Berkus, Oprah’s designer friend, came to the rescue and rebuilt their house. It came out better than the old one. Frannie was just a memorable person with a big heart that doing one good thing for her was not enough for Oprah.

5. Legends Ball and legendary gifts

The Legends Ball is a 72-hour long celebration held by Oprah Winfrey in 2005. It was an event that honors 25 African American women in the fields of entertainment, civil rights, and the arts. The event was held in Oprah’s Montecito home. The younger African American women were not left out, they were invited as well, and they were called the young’uns. Celebrities like Janet Jackson, Tyra Banks, Naomi Campbell, Alicia Keys, and Halle Berry. At the end of the event, Oprah did what she did best and surprised the group of outstanding women yet again. As if the event and luncheon and recognition was not enough.

All guests were given diamond earrings. She gave all 25 legends drop earrings, and the young’uns also received hoop earrings. What a way to cap the event, and nobody but the one and only Oprah Winfrey can pull off. Among the 25 legends were Maya Angelou, Aretha Franklin, Rosa Parks, Diana Ross, Tina Turner, Dionne Warwick, Mariah Carey, Roberta Flack, Nancy Wilson, and Alice Walker. These are 25 of history’s most influential and most celebrated women in history. They all defied odds and rose to the top of their respective fields. When will Oprah get to attend a ball like this honoring her? Who will do it for her, we wonder…

4. Jackie and SNL

A letter was sent by a girl named Peggy to the show. She talked about a girl with straight As in Michigan University. A girl who loves improv and is a member of the comedy club at school. She likes SNL because she loves to laugh. She is Jackie. She was forced to leave college because she had cancer. The producers wanted to help Jackie, maybe give her something that she will remember for the rest of her life. Oprah’s show made it all happen. First, they contacted Saturday Night Live. Through the help of Gilda’s Club (named after SNL cast member Gilda Radner who died of cancer), Jackie’s dream of watching a SNL show was met with tickets to a taping.

With Justin Timberlake hosting, Oprah feels it’s still not enough and they could do a bit more for Jackie. They then worked on another thing. They sent Jackie on Oprah’s show, after reading Peggy’s letter, Oprah calls Jackie to the stage. Out came SNL cast members Andy Samberg, Kristen Wiig, and Jason Sudeikis. They greeted Jackie, then announced they have tickets for her to see the show and their guest host Justin Timberlake. It was a precious and heartwarming moment for Jackie and for everyone else in the studio, and to millions of people watching. Another person given the gift that no amount of money can buy. Just another day in Oprah’s show.

3. Patricia Lofton’s gift

What would you do if you found out that you are actually Oprah Winfrey’s sister? Would you go to the press and announce it to the whole world? Would you reach out to Oprah and meet with her? Patricia Lofton’s mother was Vernita Lee, she was immediately given up for adoption after getting born. She was born ten years after Oprah was born. We’re actually asking the wrong questions here. The question should be what would Oprah do? Well, this is what she did.

Oprah learned of her sister in 2010, then met her in 2011. There, she learned that her half-sister was clutching a dream close to her heart. Something she was not able to do for a number of reasons, just to finish school and be a social worker. Being a modern-day Genie to the regular person, this was a walk in the park for Oprah. But this woman was no regular person to Oprah, this was her own blood. It was her half-sister. She did not just want to give her one pampered, special day, send her on a vacation, and give her a new car. Those are things she does for total strangers. For her own sister, first she gave her a house worth half a million dollars. She also made sure money will be never be a problem for her little sis, so she sent her a monthly allowance. This allowed her to graduate and follow her dream. That’s what Oprah did!

2. You get a car!

The concept of the free car was a golden idea, one that Gayle King inadvertently jump-started. She was sitting next to an executive for Pontiac in a flight and started talking about Pontiacs as a giveaway. From there, Pontiac offered 25 cars to give out, but these Oprah producers are like sharks, they smelled the blood. They made Pontiac give up cars for every audience that sits on a show, a total of 276 Pontiac G6s, then worth almost $10 million. They even researched the audience members to include people who need new cars by handing out targeted survey questionnaires

It was a successful and pivotal show, but they did not cover all the bases on this one. The show forgot about the gift tax worth about $7,000 each. They took care of the registration and sales tax, but missed the gift tax. It was not how they wanted it to end. But years later in 2010, they took another shot at it, made sure everything is covered, and launched another You Get A Car show and went with the 2012 Volkswagen Beetle this time. Each car was worth $21,000 and no one paid any kind of tax, just keys to their new car.

1. Oprah’s Favorite Things

Oprah’s Favorite Things had long been a staple segment on The Oprah WInfrey Show. Now that the show is no longer airing, the segment is still being featured and shown in The O Magazine and on Rachael Ray. Blanketed both by Harpo Productions, these two are still under the influence of Oprah, in a way. We also see something of the same nature in Ellen DeGeneres’s show. Ellen’s version is featured every Christmas season, Oprah’s Favorite Things is shown every Thanksgiving season.

The segment started as early as 1998 and was aired annually every Thanksgiving week. It got its name from a holiday song from The Sound of Music titled My Favorite Things. These favorite things are assorted products, usually for women, that Oprah thinks would be a great gift to give to friends and loved ones. What’s exciting is that most of the time, the audience watching the show get to take home some, or all of the products, shown in the segment. It was a great way to promote a product, something the great minds of the show put together and made their own. The endorsement from her show boosts any company’s sales for that season, some even not able to take the sudden rise in demand as effectively promoted by Oprah’s show. A pop culture, Oprah’s Favorite Things is a revolution in the entertainment, endorsement, and promotion industry and a trailblazer in the business.

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