If you used to be a fan of the Oprah Winfrey Show, then you might remember one of her successful makeover participants, and the shock it gave his wife when the final results were revealed.
Watching makeovers remains a favorite pastime for audiences everywhere. It’s something we’ll watch in fictional movies or in reality shows. Someone or something is getting changed? Then we want to be there to see it!
Today, shows or TV segments revolving around makeovers are a dime a dozen. But back in the day, the fabulous Oprah Winfrey is the one who truly set the standard for what people should expect to experience in a simple makeover. Her makeovers were never about changing the person themselves, or even changing their habits. They were about helping people realize the beautiful people they always were underneath the, perhaps poor, style choices they were making.
That’s exactly what Oprah did for these two men that fateful day in 2003. While both men experienced transformations that left the audience cheering, for one of them the transformation was so startling that it had audiences picking their jaws off the floor.
Classic Oprah Winfrey
The Oprah Winfrey show was THE daytime TV show to watch. Gracing our screens for 25 seasons from 1986 to 2011, we all hoped it was a show that would continue forever. Reportedly, an estimated 42 billion people watched it every week, making it the highest rated daytime talk show watched in the United States. It wasn’t just loved by audiences, but by critics as well, leading to its impressive 47 Daytime Emmy Award wins. The only reason it didn’t win more is because Oprah felt she needed to be fair to the other deserving shows on air, and so she chose to stop submitting her show for consideration. What a woman!
Beating the odds
While today she might be a worldwide icon, Oprah did not always lead the glamorous life she does now. She had a challenging childhood, and had to face a lot of adversity throughout her younger years. For a large portion of her life she lived in poverty and experienced unspeakable things that no young woman should face including assault, teen pregnancy, and a miscarriage. But in true rags to riches fashion, Oprah wasn’t going to let any of these obstacles stand in her way. Instead, she used her experiences to drive her and push her towards reaching her goals, something she has accomplished beyond all of her wildest dreams.
An inspiration to us all
For many, Oprah is a true inspiration. Some might even call her a hero. In the mid ‘70s Oprah became the first black woman to anchor the news at WLAC-TV, which inspired black women across the country. In 1998, she established her charity Oprah’s Angel Network, which has contributed over $80 million to projects across the globe. Not only did she find huge success, but she has used it to help others and be as generous as possible. Many are even hoping she’ll consider running for president in the next election!
Making the world a better place
One of the things people adored about The Oprah Winfrey Show were the moments where they could witness someone’s life change for the better, right before their eyes. Today we might be used to seeing something like it on shows like Ellen, but Oprah is the one who truly created something from this idea. Viewers everywhere would contact the show and nominate their family, friends, or even themselves, for something they believe was needed to make their lives better.
Hair, hair, everywhere
Getting picked for one of Oprah’s signature transformations didn’t always require a nomination. For one man in Chicago, all it took was for the show’s producers to see him walking by and decide to offer him a makeover. After they convinced him they could help him ditch his dull look with the help of their trust “Fab 5” crew of stylists, Roland Jones took the producers up on their offer. But no one could have anticipated what would happen next.
When Roland showed up to the show he brought his wife and kids with him. His wife, Kimberly, told Oprah that she had never seen her husband without his beard. His daughters agreed, saying they had no recollection of ever seeing their father beardless in over 20 years. The studio audience had a laugh as pictures of Roland were shared across the screen. It was pretty clear that this was a man who had never gone without a beard in his adult life…so maybe the time had come!
Contestant number two
Roland wasn’t the only bearded individual seeking a makeover. The other star of the episode was Gerald, a man who had been nominated for the show by his wife begging to see him with a new look. Gerald’s wife explains that when she first fell in love with her husband he was handsome and clean shaven, but over time he stopped shaving and let himself go. She couldn’t even remember the last time he had a haircut.
Plea for help
As photo’s of Gerald flashed across the screen, Fiona, his wife, continued to desperately beg for help. She pleaded with Oprah to help Gerald update his look, get rid of his awful unibrow, and get him back to the handsome man he once was. Her plea drew laughter from the audience, but little did they know what they would see when the Fab 5 got through with him. The time for the men to transform was about to begin.
The professional’s take
Before Gerald and Roland could be taken backstage for their makeovers, Oprah invited the grooming expert, Kyan Douglas, to weigh in on some of the issues they would be addressing. Using his expert opinion, Kyan was quick to point out Gerald’s lovely eyes, but shared his dismay that they were being masked by his crazy eyebrows! Roland’s eyes presented a similar problem. Kyan believed that both men were clearly “creative guys” and he hoped that their new looks would help reflect that.
Let the work begin
The time had arrived for the magic to begin. Roland and Gerald were whisked away backstage, and the Fab 5 got to work. It was decided that both men would receive new haircuts to better suit their faces, and the beards would likely have to go as well. And of course, some major work was going to be done on those long and bushy eyebrows. But some were skeptical, could the stylists really transform these men the way their wives wanted? Well, they were going to find out soon.
The first amazing transformation
The first big reveal was the unveiling of the new and improved Gerald. All his wife wanted was to be able to see his lovely face, and not a “total hippy” like he was before. The audience wasn’t sure what to expect, but as Gerald stepped through the curtain gasps and screams could be heard around the room. He was almost unrecognizable compared to the man he was before, and his wife looked like she was in complete shock.
A clean and young look
Gone was the long hippy hair, the beard, and the bushy unibrow. Instead, Gerald stood before the audience looking like a young man with a cleaned up look. Gerald couldn’t keep the smile off his face as Kyan talked through what he had done. The choppy hair look was done using straight edge razors, they shaved the beard completely, and attacked that unibrow until it was groomed to perfection. He looked like a brand new man, but his makeover wasn’t even the most shocking one of the day.
A complete metamorphosis
No one could have predicted the shocking transformation they would witness when Roland stepped out for his big reveal. It was hard to believe they were even the same person! His sister, who was in the audience, couldn’t believe his fashionable clothes and new look, and shouted, “You look 19 again, bud!” Gone was the drab hippy, and in his place was a handsome man sporting jeans and a blazer.
The handsome gentleman in grey
Before his transformation some compared Roland’s look to that of a grizzly bear in hibernation, but once the Fab 5 were through with him that look was gone. It seemed miraculous! His long hair was replaced by a much more chic cut, giving him the look of a silver fox. Add in the clean shaven face and he looked years younger. Like Gerald, some work was also done on his eyebrows. People could hardly believe what they were seeing.
The shock of a lifetime
The audience was obviously in shock, but that was nothing compared to the total shock his wife, Kimberly, was in. Before the makeover, many had commented on how different she looked from her husband as a well groomed woman, but that certainly wasn’t the case now! As the cameras panned to her face it was clear she was completely surprised and elated. All it took was a chance meeting in Chicago and now her husband looked like the man he should be. Kimberly could barely hold back her excitement.
The daughters’ shock
Roland’s wife was beyond surprised, but nothing could have prepared people to see the reactions from his daughters. The look on their faces really said it all. Jaws dropped, hands flew to their mouths, and they were clearly emotional. After decades of seeing their father with long hair and a beard his new look was astounding to them. Finally, after all this time, they could see the handsome man that had always lurked underneath all the hair.
The eyes have it
Kyan Douglas saw beneath the bushy eyebrows what others couldn’t, that these men, especially Roland, had some gorgeous eyes just waiting to be shown off. People couldn’t take their own eyes off Roland’s hypnotizing blue ones. Oprah, impressed with the makeover herself, asked Roland how he felt about it. He was very pleased and said, “I feel like I’m alive again,” which brought out emotional cheers from the audience. The transformation affected Roland both physically and mentally.
Roland and Gerald are hardly the only two people to have been given a makeover by Oprah and her team. It would be nearly impossible to count the hundreds, or possibly thousands, of transformations that took place on 25 seasons of the Oprah Winfrey Show. Even today, the clips of the many makeovers on her show continue to garner millions of views on YouTube. It’s amazing to see what just a change of clothes and haircut could do for a person.
Back in 2002, one couple came on the show for a makeover and they quickly became fan favorites. Dubbed the “Rock and Roll Hair Couple,” Tim and Wendy White arrived on the show after being nominated by their friends. Both had long listless hair, and neither knew how to use their hair in fashionable styles. It had been ages since either of them had tried out a new hairstyle, so what could Oprah do for these people clearly stuck in a different era?
Oprah and her team showed off their skill, and certainly did not disappoint, with these transformations. Wendy made her debut first with short curled hair that had been dyed blonde. Next up was Tim, whose hair had been cut short, but was still left with a bit of edge to give it that rock and roll vibe. When the two see each other they are both surprised, but also excited. They had finally stepped out of the past, and now looked like a cool hip couple out on the town.
Saying goodbye to the caveman
For the makeover of bearded Josh, Oprah enlisted the help of her friend Tim Gunn, the well known fashion expert and television personality. Sporting a wild “caveman” like beard, Oprah received a plea from his girlfriend, Heidi, to help take it away and make him “a little less hairy.” Tim and his team shaved the beard and cut Josh’s hair, creating a handsome and young looking man. However, Tim did leave a tiny bit of the beard because he didn’t want to change Josh completely.
On the same episode, Tim Gunn also helped with one of Oprah’s more memorable makeovers. Like they had with Roland, Jason was picked out by the production when they spotted him in a hardware store wearing baggy overalls and an unkempt beard. People couldn’t believe their eyes when Jason walked out of his makeover beardless, sharply dressed, and with a stylish cowboy hat. Oprah even thought he looked like country music star Kenny Chesney, and the audience agreed. This cowboy came out a new man and couldn’t be happier about it!
Mother knows best
Men and couples weren’t the only ones getting makeovers on the Oprah Winfrey Show. In one particular case, a teenage girl named Jocelyn was nominated by her mother for a necessary makeover. Taking it back to 1993, the audience was introduced to Jocelyn and her mother, who was not a fan of her daughter’s clothing choices and was even embarrassed to be seen with her in public! Oprah’s team gave Jocelyn a pretty standard ‘90s makeover, but unlike most other participants Jocelyn was not pleased with her results.
The fashion couple
In another exciting episode, Oprah meets John and Kate (no not the reality stars you’re thinking of). The two 26 year olds didn’t own an iron, had heaps of wrinkled clothes, and felt like they had fallen into a fashion rut. They even got Kate’s grandmother to beg Oprah to help them out. The end result was surprising to the family, not just because of the makeover, but because of the new engagement ring Kate was sporting!
From sweaters to fishnets
Moms work hard, and sometimes they find themselves veering away from the things they need to do to take care of themselves and make them feel good. Oprah took this idea, and in 2003 devoted her makeovers to moms. One memorable mom was Heather, who was stuck in a pattern of dressing in unflattering holiday sweaters. Her husband even joked that she looked like her own mom. But when Heather strut on stage in her hot new look she got the last laugh, and even attempted a pole dance routine to the audience’s delight.
Toning it down
Makeovers weren’t just about the people who needed to be adding something extra to their look. Oprah’s show also featured people who needed some help toning down their makeup and clothes. This was the case for Jan, a woman who used massive amounts of hairspray on her bun, and wore tons of makeup. She even wore makeup to bed out of fear that someone might see her! Luckily, Oprah’s team helped teach Jan the art of subtlety by toning down the makeup and fixing her hair. The result was beautiful!
When extensions go wrong
In 2010, viewers witnessed another “makeunder” featuring Dawn, a blonde bombshell from Canada who was dressing like a teenager instead of a mature woman. Joining Oprah for this makeover was TV personality Carson Kressley. Between her crazy hair extensions and cosmetics, even Dawn’s kids were being teased about her looks. But when the transformation was complete the kids were stunned to see the polished and sophisticated woman before them. Unfortunately, Dawn later returned to the use of her hair extensions after a bout of depression.
Getting their groove back
Carson also helped Oprah with another makeover featuring Nina and Randy, a cute New York couple. Once upon a time, they were a hip young couple in New York City, but later after moving to a farm upstate, their fashion took a hit. Despite Nina formerly working in the fashion industry, they still ended up stuck wearing plaid shirts and work shoes on a daily basis. The couple was taken on a shopping spree to spruce up their wardrobes, and given brand new looks, much to everyone’s enjoyment.
The transformation of Oprah
Over the years, Oprah helped countless numbers of people with their own makeovers, but one of the most unforgettable makeovers was her very own. Oprah has been very open about her battle with weight, and she has often shared that journey with her public. In 1988, viewers were shocked when Oprah stepped out to reveal she had lost 67 pounds! She even demonstrated the amount in a wagon filled with animal fat. But the transformation came with consequences the viewers didn’t see.
Years later, Oprah revealed that in order to lose those 67 pounds she had practically starved herself for four months. She retreated away from events and said, “Anything that involved being around food at all I just cancelled.” Many questioned her motivations for losing the weight, with some believing she did it to please her long time partner Stedman Graham. Oprah denied those rumors and expressed that something like this should not be done for anyone but yourself.