Oprah Winfrey’s iconic 'Favorite Things' segment is more than just a pop culture phenomenon—it’s a heartwarming tradition born from her genuine desire to share joy. But here’s where it gets fascinating: it all started with something as simple as a pair of pajamas. Yes, you read that right. Long before the legendary car giveaways, Oprah was already spreading happiness in a much cozier way. So, how did a love for plaid PJs evolve into one of TV’s most talked-about segments? Let’s dive in.
We’ve all heard Oprah’s unforgettable catchphrase, 'You get a car! You get a car! Everybody gets a car!' But the origins of her Favorite Things segment are far more humble—and surprisingly relatable. It began with Oprah treating her own staff to the things she personally adored. In a recent social media reveal, Oprah, alongside her longtime friend Gayle King and Oprah Daily’s creative director Adam Glassman, shared the heartwarming backstory behind the segment that became a holiday staple for 25 seasons of The Oprah Winfrey Show.
And this is the part most people miss: it all started with pajamas. Oprah recalled, 'I had a pair of plaid pajamas that I loved so much, I got one for everybody on my staff.' But it didn’t stop there. When she discovered Uggs, she took her generosity to the next level. 'I got everybody’s shoe sizes and handed out Uggs,' she explained. A brilliant producer then suggested, 'Why not do this for the whole audience?' The rest, as they say, is history.
Here’s where it gets controversial: While the car giveaway became the most famous Favorite Things moment, Oprah’s love for pajamas never faded. Gayle jokingly recalled, 'I hope you’re not giving out pajamas,' to which Oprah quipped, 'I don’t think it could get much better than pajamas.' But let’s be real—would you rather have a car or the coziest PJs ever? Let us know in the comments!
Over the years, the segment grew into a holiday tradition, airing annually from 1996 to 2008, with brief returns in 2010 and 2017 on The Rachael Ray Show. Today, Oprah’s team scours the globe for 'magical presents' that earn her stamp of approval, from weighted blankets to blue light-blocking glasses. As Oprah herself puts it, 'Life is better when you share it.'
So, as the holidays approach, take a cue from Oprah: whether it’s a pair of pajamas or something grander, the joy of giving is what truly matters. But here’s the question: What’s the most thoughtful gift you’ve ever given or received? Share your stories below—we’d love to hear them!
