Jon Stewart Reveals the Advice from David Letterman That Changed His Life Forever

Jon Stewart recently shared a memorable piece of advice he received from fellow late-night legend David Letterman, which he considers the best he’s ever gotten. During a Q&A session with The Daily Show audience, Stewart was asked about the best advice he had ever received. After some initial humor about the nature of such a profound question, he recounted an experience from his early career that left a lasting impression.

In the early 1990s, Stewart hosted The Jon Stewart Show on MTV. The show quickly gained popularity, leading to its expansion into an hour-long syndicated series meant to fill the slot left by Arsenio Hall. However, despite its initial success, the show was ultimately canceled after about nine months. This cancellation was a significant blow to Stewart, who felt the sting of having his name associated with a failed venture.

During the final episode of The Jon Stewart Show, David Letterman appeared as a guest. Letterman, a seasoned late-night host, offered Stewart a piece of wisdom that has stayed with him: “Don’t confuse cancellation with failure.” This advice helped Stewart reframe his experience, distinguishing between the end of a show and a personal failure. However, in typical Letterman fashion, he humorously added during a commercial break that the show was indeed a failure — just to ensure Stewart didn’t misunderstand.

Stewart reflected on his early days in comedy, noting that mentorship was not as prevalent during his rise in the 1970s and ’80s. He described his development in the industry as somewhat “feral,” lacking the guidance that many young comedians might seek today. The advice from Letterman stood out because it came at a moment when Stewart needed it most, offering a perspective that helped him move forward in his career.

The Jon Stewart Show may have had a brief run, but it laid the foundation for Stewart’s future success. Despite its cancellation, the experience provided Stewart with valuable lessons that would later influence his approach as the host of The Daily Show, where he would go on to achieve unbelievable success.