For over 30 years, David Letterman hosted some of the most iconic and groundbreaking late-night talk shows. Known for his quick wit and ability to roast any guest, Letterman became a legendary figure. But one night in early 2021, the tables were turned in a very unexpected way.

It all started when Meghan Markle, The Duchess of Sussex, agreed to appear as a guest on Letterman’s Netflix talk show, “My Next Guest Needs No Introduction.” As one of the most famous women in the world, Meghan’s every move was closely watched, but no one could have predicted what would unfold during her interview with Letterman.

As the taping began, Letterman came out and greeted Meghan warmly. He started by asking her general questions about living in California with Prince Harry and their young son Archie. Meghan spoke candidly about adjusting to a new life outside the royal family and discussed the challenges of being in the public eye. Letterman seemed genuinely interested in learning about Meghan’s experiences.

But then, without any warning, Meghan launched into a comedic roast of Letterman that had everyone stunned. She started by pointing out Letterman’s signature scraggly beard and joking that she was surprised he hadn’t tried to braid it into a “beard beard” yet. Letterman let out a surprised chuckle as the audience roared with laughter.

Meghan wasn’t done though. Next, she zeroed in on Letterman’s love of pranking guests on his old late-night show. She hilariously called him out, saying, “Dave, we all know your reputation for tormenting unsuspecting celebrities, but let’s be real, at this point your only victim is that mirror you stare into every morning before filming.” By now, Letterman was laughing so hard he could barely catch his breath.

But Meghan was just getting warmed up. She quipped that thanks to the isolation of the pandemic, Letterman finally had enough free time to binge old episodes of her show “Suits.” She gently reminded him that while he may know her backstory now, “it’s past your bedtime, Grandpa Dave.” The audience was howling at this point, completely shocked by Meghan’s comedic chops. Even Letterman seemed stunned, having never experienced anyone turning the tables on him like this. He wiped tears of mirth from his eyes and begged Meghan to stop, but she ignored his pleas.

Meghan then jokingly roasted Letterman about rumors of his retirement, suggesting he was merely waiting for the right successor to take over his throne of tormenting guests. She even cracked that he was holding out hope his dream candidate, Regis Philbin, would finally cave and come out of retirement. By the time Meghan wrapped up her playful roast, Letterman was visibly red-faced from laughing so vigorously. The entire studio audience and Netflix crew were on their feet, cheering wildly for Meghan.

It was truly a hilarious and unexpected way for the interview to unfold. Seeing how much Meghan had won over the audience with her comedic timing and witty barbs, Letterman eagerly shifted gears to discuss comedy more deeply with her. He commended her surprise comedy skills, questioning how she developed such a talent for roasting.

Meghan explained that growing up in a big, loud family in America helped prepare her early on to be able to give as good as she got. She also cited her study of theater and communications in college as helping polish her comedic chops. But most importantly, she credited growing up in 2020 as the ultimate crash course in taking a joke and having a thick skin.

From there, Letterman and Meghan engaged in a fascinating discussion about the power of comedy, cancel culture, and finding common ground through humor even in divisive times. Their insights into the art of friendly roasting and using light-hearted jokes to bring people together were truly thought-provoking.

By the end of the hour-long episode, Letterman was still beaming from the unexpected hilarity Meghan had unleashed. In a heartfelt closing, he thanked her for reminding him why he loved his career all these years: for the joy of connecting with guests through genuine conversation and laughter.

The episode instantly became one of the most talked-about moments of the year among late-night fans worldwide. Meghan had definitively stolen the spotlight by completely surprising them all with her epic roast of the legendary Dave Letterman himself. It was a master class in comedic timing and charisma that won’t soon be forgotten. 

Well, that wraps up the story of the night David Letterman became the roasted guest instead of the roaster. What an unforgettable showcase of Meghan Markle’s hidden talents! She definitely cemented her reputation as one of the wittiest roasters in the business.

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