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20 Most Expensive Things Oprah Bought For Her Friends And Family

Oprah Winfrey may be a billionaire, once sharing the cover of Forbes along with the likes of Bill Gates and Warren Buffet, but she didn't get there through frugality or stinginess. Oprah famously built her fortune from nothing. She was born into poverty in rural Mississippi, but began to make her mark early in life, and was already co-anchoring her local news station at the age of 19. She was quickly transferred to daytime TV and eventually succeeded with her own show. After decades of success, Oprah retired from her chat show, but only to start her own media empire, with a magazine, website and television network. She also still acts in and produces movies. Oprah is currently the richest African American person and has been named one of the most influential women in the world. She is a force to be reckoned with, and is a classy and kind-hearted person to boot.

The chat show queen is currently worth nearly 3 billion and she is known for her consistent generosity and philanthropy, to audiences, to friends and family, and even to strangers over the internet. There have been many memes based on her love of surprising people with expensive and over-the-top gifts. She is all about sharing her wealth, and sometimes she really goes all out with the gifts she gives to her loved ones. Here are 20 times Oprah went above and beyond with extravagant gifts.

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20 Oprah Gave Diamond Earrings To A Bunch Of Celebrity Friends

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In 2006, Oprah threw a “Legend’s Ball,” which celebrated 25 African American women who were prominent in entertainment, art, and civil rights. The three-day event involved a luncheon held at Oprah’s Montecito home, and the highlight was a white-tie ball.

The 25 celebrated women included Maya Angelou, Aretha Franklin, Toni Morrison, Rosa Parks, Diana Ross, and Tina Turner. Many younger African American women were also involved, including Alicia Keys, Halle Berry, Naomi Campbell, Tyra Banks, and Janet Jackson.

Footage of the event was later condensed into a one-hour documentary showcasing interviews of the attendees and “behind the scenes” moments from the ball. The event culminated in a gospel luncheon, during which reportedly there were many spontaneous performances by attendees. At the end of the luncheon, Oprah surprised all her guests with a pair of diamond earrings, giving drop earrings to the “Legends” and hoop earrings to the “young’uns.”

19 Oprah Gave Her Step-Mother An Expensive Cruise

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Oprah’s father Vernon Winfrey married Barbara Winfrey when Oprah was in her 40s, and they divorced 14 years later with much bitterness between the star and her stepmother. However, before the divorce, Barbara has admitted that Oprah treated her and Vernon to an “amazing” private 11-day Mediterranean cruise.

The mega-wealthy celebrity rented a yacht worth $30 million and brought along her partner Stedman and best friend Gayle. The cruise included three-course meals three times a day, with full table settings and all the trimmings.

Barbara was disappointed that she didn’t get to spend more time with Oprah on the cruise, later accusing her of spending too much time with friend Gayle King. However, these accusations were only made after the divorce, when Barbara was asked to leave the $1.4 million mansion she had shared with Oprah’s father.

18 Oprah Gave School Uniforms, And A School, To Girls In South Africa

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Oprah founded a $40 million school in South Africa, known as the Oprah Winfrey Leadership Academy for Girls, after a discussion with Nelson Mandela. At the time she said, "When you go to Nelson Mandela's house, what do you take? You can't bring a candle."

The school opened in 2007 with a lavish ribbon-cutting ceremony attended by Spike Lee, Nelson Mandela, and Tina Turner, as well as Oprah herself, and has since accepted hundreds of students.

The students are selected from disadvantaged backgrounds, and many of them come from families devastated by AIDS. However, Oprah’s generosity did not end at creating the school. She personally ensures that all the girls are fed and clothed and will call them personally when they are sick (which is a gesture very much appreciated by the often orphaned students). Since its opening, Oprah has spent well over $100 million on her not-a-candle for Nelson Mandela, but she appears to have no regrets.

17 Oprah Gave Everyone A Car

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Oprah is perhaps most famous for giving each of her entire studio audience a new car in 2004 to kick off her 19th season. The audience believed originally that only a handful of those present would receive a car, and were each given gift boxes that they thought might contain a key. In a surprise twist, every box had a key to a new car in it.

The episode even spawned a meme, with Oprah announcing, “You get a car, you get a car, everyone gets a car!” Overall, 276 Pontiac G-Sixes were given away to a handpicked audience. Oprah had ensured that every member of the audience was a fan of the show and that they needed a new car.

She also had paramedics standing by in the studio, in case the excitement was too much for any of the audience members. Unfortunately, it later emerged that each person would be required to pay up to $7000 in tax for their new car, as they were classified as “prizes.” However, The Oprah Winfrey Show producers did offer to give audience members a cash prize in lieu of the vehicle if they preferred.

16 Oprah Gave Her Audiences Myriad Gifts, Including A Private Vacation With Her

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Cars are not the only giveaway Oprah had on her show, of course. Giving expensive presents to a shocked audience was a staple of the show. Her surprises have varied from thousand dollar scholarships, to iPads, to Mariah Carey concerts. She has also given away somewhat bizarre items, such as a refrigerator with a television and DVD player in it, and free KFC vouchers for everyone. And that really meant everyone in the country, and not just her audience (there was a voucher on her website that could be downloaded at the time).

Oprah always tried to make the surprise special to the audience, picking people who needed, or would really appreciate the gift. And when she really wanted to do something special, she would treat her fans to a holiday. Oprah took entire audiences, of hundreds of people, on holidays to Philadelphia and Disney World.

Finally, for her final season, Oprah handpicked an audience of The Oprah Winfrey Show superfans and took them to Australia for an 8-day vacation with her.

15 Oprah Gave Her Workmates A Juicer

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The Oprah Winfrey Show finished in 2011, but Oprah has continued to stay in the spotlight as an actress and producer. In 2017 she was filming A Wrinkle In Time on location in New Zealand, along with Mindy Kaling, Reese Witherspoon, and Chris Pine. However, when the film wrapped, Oprah couldn’t help but return to her roots as a talk show host. She demonstrated her favorite juicer for her fellow cast members, right before gifting each one of them with the $400 appliance. The cast and crew were appreciative of the gift but may not have been thankful for long. The juicer that Oprah gave them was the Juicero, the product of a short-lived start-up that went out of business by the end of 2017. The Juicero is widely mocked now as it turned out to be nothing more than a gadget to squeeze out bags of already-juiced fruits and vegetables that were sold on subscription. However, the company has offered refunds for its customers, so Oprah might not have been wrong when she called this "The wrap gift that keeps giving.”

14 Oprah Bought A Warehouse Of Her Partner's Books To Help His Sales

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Oprah has been with her partner Stedman Graham since 1986. They were engaged to be married in 1992 but didn’t proceed with the ceremony. They have both since said that they don’t believe they were meant to marry and that it might have ruined their relationship if they had gone through with it. Graham is the CEO of S. Graham & Associates, a marketing consulting firm, and has published over ten books.

There has been a lot of speculation about their unconventional relationship over the years, fuelled by rumors that Oprah is actually in a romantic coupling with her best friend, Gayle King. Oprah’s ex-stepmother fanned the flames of these rumors by claiming she had never seen Oprah and Stedman be physically affectionate with each other in public (although there are plenty of paparazzi photos available to prove otherwise.

However, she also claimed that Oprah bought a “warehouse” of Stedman’s books in order to place him on bestseller lists.

This accusation may or may not be true but, if so, it was an extremely generous – and publicly risky – gift for a partner that Oprah supposedly doesn’t really care about.

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13 Oprah Threw Gayle King An Extravagant 60th Birthday

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Gayle King has been best friends with Oprah since they were both in their 20s (for around 40 years). She was once the host of her own show and has since been made an editor of O, The Oprah Magazine. She is also co-anchor of the CBS News morning show CBS This Morning. In acknowledgment of their long friendship, Oprah threw Gayle an extravagant 60th birthday party.

The theme of the shindig was “The World According To Gayle” and included all of her favorite foods, such as burgers, cheese melts, popcorn, and various desserts. The “birthday cake” was a massive tray of cupcakes, arranged to spell out birthday wishes with chocolate and yellow icing. All the guests were asked to wear yellow, which is Gayle’s favorite color.

Oprah arranged for Gayle’s children and her co-host on This Morning, Charlie Rose, to attend the surprise birthday party, even though it meant that Rose had to miss the White House Christmas party, which was held on the same day.

12 Oprah Took Gayle And Kirby Truffle Hunting In Italy

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Gayle King’s 60th birthday bash was only one of a long line of gifts Oprah has given her best friend over the years. Frequently, when Oprah goes on vacation, Gayle will join her. Most recently, the billionaire flew Gayle and her daughter Kirby over to Umbria, Italy so that they could go truffle hunting together. Oprah has never made a secret of her obsession with truffles and has said that she takes truffle salt with her whenever she travels. She traced the obsession back to when she was given a gift basket by Mariah Carey, which contained a truffle salt shaker. Participating in a genuine truffle hunt has been on Oprah’s bucket list for years. In 2017 she finally got the chance to go and treated her BFF to the trip.

The trio went out with traditional truffle hunters and dogs and managed to find Oprah a bag of 15 white truffles, which can sell for up to $10,000 per pound (Oprah estimated that her bag was almost a pound worth of the valuable fungus).

The hunt ended with a feast of homemade pasta, gourmet pizza and, of course, truffles seasoning everything in sight.

11 Gayle King's Favorite Gift From Oprah Was A Live-In Nanny

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While Oprah has given her BFF Gayle King many expensive gifts over the years, Gayle has admitted that the gift that she appreciated the most was quite unconventional. On the show Watch What Happens Live, in 2017, Gayle explained to host Andy Cohen that her favorite gift from Oprah was a live-in nanny.  Gayle had her second child only 11 months after her first and called it a moment when you say to the doctor, ‘I thought this diaphragm was supposed to work.’

She was completely overwhelmed having two infant children in her care and said that, at the time, she could never have afforded to hire the nanny on her own.

Gayle has always considered Oprah a generous friend, even on the first night they met, when both were working at a Baltimore TV station. The station was hit by a powerful snowstorm and Oprah invited her future BFF to her house to spend the night when she realized Gayle wouldn’t be able to reach her own home. Oprah was earning only $22,000 a year at that point but still bought them both sweaters to wear, as they didn’t have appropriate clothes for the weather.

10 Oprah Hosted A 3-Day Extravaganza At Mar-a-Lago For Maya Angelou

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Oprah considered the author and poet Dr. Maya Angelou to be one of her closest friends, describing her as a “mentor-mother-sister-friend.” So when Dr. Angelou turned 80 in 2008, Oprah wasn’t likely to let the event pass without recognition. She held a 3-day gala, with 500 attendees, in the poet’s honor, which reportedly cost her around $4 million. Perhaps even more extraordinary is that Oprah managed to convince Donald Trump to let her hold the gala at the Palm Beach Mar-a-Lago resort, closing it to the public during a busy weekend.

The grand ballroom of the resort was set with several marble stages and hosted a wide array of talent, including Donna Summer and Tony Bennett. This might, however, be eclipsed by Oprah’s present to her friend for her 70th birthday, which was a week-long Caribbean cruise for the poet and 150 of her friends.

9 Oprah Held A Wonder-Woman Party For 28 Girls

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In 2017, Oprah held a “Wonder Woman Day” in honor of the release of the female-led superhero film. She invited 28 ten-year-old girls and their parents to her house in Montecito, Los Angeles for the celebration. The party featured a cake from local bakery Charm City Cakes with a large Wonder Woman shaped fondant topper, on top of red and gold icing. The party was also catered with plenty of barbecued hot dogs and hamburgers, as well as popcorn served in large Wonder Woman themed tins. Oprah also provided everyone with Wonder Woman flip-flops and dressed herself and her dog, Sadie, in the super heroine’s signature gold tiara.

Oprah documented the process of putting together the party behind the scenes through her Instagram account. She even earned the approval of Wonder Woman herself, Gal Gadot, who reposted one of Oprah’s videos of the day, saying “This is awesome!”

8 Oprah Treated Her Staff To A Two-Week Mediterranean Holiday

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In 2009, Oprah decided to try for the title of World’s Best Boss by treating her staff at The Oprah Winfrey Show to an all-expenses-paid Mediterranean cruise.

The media mogul kicked off the two week holiday by renting out the Poble Espanyol, a recreated Spanish village with restaurants and bars, and featuring traditional dancers and concerts.

She celebrated her 55th birthday there, surrounded by her staff and their families, around 1700 people. Her staff stayed in the rented village for 3 days and were then treated to a 10-day cruise on the Norwegian Gem liner. They sailed from Barcelona and visited Italy, Turkey, Greece, and Balta along the way.

Oprah paid for everything, including transport, entertainment, and meals. This was estimated to cost over $5400 per person for each of her employees and their family members.

7 Oprah Took Her Employees To Hawaii

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If you work for Oprah you can expect a few perks.

In 2016, she took around 40 of the staff of her magazine on an all-expenses-paid trip to Hawaii to celebrate her birthday. The only catch was that the chat show queen had recently bought a 10% share of Weight Watchers and the staff were expected to participate in healthy activities and earn “fit points.”

Oprah spent the morning of her birthday waking at the crack of dawn to go for a hike with her “dream team.” It was later announced that the entire group of staff members had lost 96 pounds in total during the week-long trip.

Oprah spends a lot of time in Hawaii and owns a relatively modest, although fully modernized farmhouse there, as well as an estimated 800 acres of land. This isn’t the first time she’s treated her staff to a vacation in Hawaii, as she took her chat show staff on a cruise there in 2000.

6 Employees Of O Magazine Got A $10,000 Check Each

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Holidays aren’t the only thing that Oprah’s staff members receive from their generous boss.

In 2010, to celebrate the 10th anniversary of the magazine O, The Oprah Magazine, Oprah gave every employee working on the lifestyle mag a check for $10,000, along with an iPad.

As if that wasn’t generous enough, each of the iPads came in a leather case, engraved with the employee’s initials. It didn’t appear to matter how long the employees had been working at the magazine either, as all of them got the same gift, even if they had only been employed for a few weeks. O Magazine has now been circulated for 18 years and remains popular. Every issue of the magazine features Oprah herself, occasionally sharing the spot with other iconic women, such as Michelle Obama and Ellen Degeneres.

5 Oprah Gives Her Housekeepers Regular Shopping Sprees

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It isn’t just the staff of her chat show and magazine who can count on Oprah’s generosity. She is also reportedly extremely generous to her personal staff, such as her housekeepers. It has been rumored that she takes her maids on a shopping spree once per month, allowing them to purchase whatever they like.

The housekeepers arrive at the designer stores in a limo, and Oprah has been seen telling them to get whatever they want in two minutes. She hands her credit card to the salesperson and says that she will pay for whatever her six housekeepers want to buy.

The shopping spree resulted in a pile of designer clothes and reportedly costs “thousands and thousands” of dollars. While generous, that amount is only a drop in the bucket for Oprah, even if she does take them out every month.

4 Oprah Gave A Fan Her Wedding Dress

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In 2014 Oprah wore a Brian Rennie for Basler white-feathered dress while posing for the cover of the magazine Essence. After the magazine hit the shelves, one of her fans from Atlanta tweeted the billionaire actress, jokingly asking for the dress, saying that Oprah won’t ever wear it again.

Twitter user @snobaby28 wrote “@oprah you look beautiful in that essence cover pic. WOW. CAN I please have that dress? Cuz I know u won't wear again lol luv u (sic)."

It must have been a shock to the fan when Oprah replied, saying, ‘“You're right I won't wear ever again contact my assistant and show her this tweet.”

Oprah was as good as her word and the fan, who was reportedly called Brandi, later said that she had received the designer dress. She sent an ecstatic thank you to Oprah, saying that she would wear the dress for her wedding “as soon as she found Mr. Right.”

3 Oprah Gave Books To Famous Kids

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It must be difficult to figure out what to get friends when you hang out with some of the world’s richest and most famous people. Oprah has had a long and illustrious career so far, and has many, many famous friends, although not many who can match her level of wealth. Beyonce and Jay Z come close, as their total worth as a couple is now over a billion dollars. So what do you get for the child of a couple who has everything? Keeping with a tradition that has also been extended to Tyler Perry’s child and the Clooney twins, Oprah reportedly gave Blue Ivy a treasure chest filled with books as a third birthday present. She clearly is one for thoughtful gifts as well as expensive and extravagant ones.

2 The Best Gift Oprah Can Give

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So what does Oprah herself say is the best gift to give? She once told her audience in an after-show chat that she considered a "grateful journal" to be the best gift someone can give you. This is a “nice, pretty” journal that you purchase and then keep for a year, writing down in it every time you are grateful for something about the person in question. The intention is to eventually give them a gift filled with thoughtful and loving memories and reasons why you love them.

This wouldn’t be an extravagant gift for the average person, but for Oprah it might be a different story. It is estimated that at the height of her success in 2011, Oprah was earning around $600 per minute. So if she took only around ten minutes of her time per week over a year to write in a ‘grateful journal’ she would end up handing over a gift worth over $300,000 to some lucky recipient. Of course, the memories contained in it would presumably be priceless.

1 Oprah Gave Her Half-Sister A House

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In 2011 Oprah revealed to the world that she had a half-sister that she had never known. Oprah was born to an unmarried, teenage mother, Vernita Lee, and was eventually sent to be raised by her biological father.

Patricia Lofton was born almost ten years later to the same mother and was quickly given up for adoption. Oprah didn’t learn that she had a half-sister until 2010, almost 50 years later. Patricia had reportedly known since 2007 that Oprah was her sister, but had refused to sell out her sister to the press. They were reunited in 2011 and that’s when Oprah discovered that her sister had a dream: to graduate from college and become a social worker.

Oprah set out to help her sister make her dream a reality. First, she bought her a $500,000 house in Wisconsin, and then she provided her with a monthly allowance. This allowed Pat to quit her job and go to college.

Finally, in 2017, at the age of 53, Pat graduated from college and fulfilled her lifelong dream. Oprah attended the graduation with Stedman, and the doting big sister sent out photos from after ceremony, expressing her pride in her “lil sis.”

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