Billy Crystal made a memorable appearance on The Late Show with Stephen Colbert, where he shared an incredible story about the night he hosted The Tonight Show and had an emotional encounter with legendary sportscaster Howard Cosell.

Crystal, an Emmy Antonio award-winning comedian with almost 50 years in the entertainment industry, was greeted with applause as he joined Colbert on the show. The conversation took an interesting turn when Colbert mentioned that former President Bill Clinton had been a recent guest on the show. Crystal revealed that he had actually interviewed Clinton live at the Beacon Theater for 90 minutes, a daunting experience considering the limited time frame for questions.

The comedian also took a moment to appreciate the hard work that talk show hosts like Colbert and “the jimmies” (Jimmy Fallon and Jimmy Kimmel) put into their nightly shows. Crystal acknowledged that their ability to seamlessly blend comedy, interviews, and music every night was extraordinary.

The conversation then moved on to one of Crystal’s most intimidating experiences as a talk show host. In 1986, Crystal had the opportunity to guest host The Tonight Show, filling in for the legendary Johnny Carson. Crystal recalled feeling nervous despite having already achieved success with Saturday Night Live. He vividly remembered the nerves he felt when he arrived at NBC and was directed towards his parking spot, which happened to be right next to Carson’s reserved spot.

Crystal’s first guest on The Tonight Show was none other than Howard Cosell, a sportscaster Crystal knew well from their shared experiences at the theater. Cosell had a variety show called Saturday Night Live before the iconic sketch comedy show, and Crystal had witnessed Cosell’s eccentricities firsthand.

Recounting the nerve-wracking night, Crystal revealed that he received a frantic call from The Tonight Show staff, informing him that Cosell did not want to do a pre-interview. Determined to make the show a success, Crystal reached out to Cosell directly. He called Cosell, who expressed his disinterest in discussing specific topics and instead insisted on having a natural conversation between friends.

As Crystal recalled, the night of the show arrived, and he was in his dressing room finalizing his monologue. Suddenly, there was a knock on the door. To his surprise, it was Cosell, who appeared to be in distress. Crystal described the scene as Cosell began to cry and leaned into his arms for support. At 6’3”, Cosell’s emotional vulnerability created a poignant movie-like moment for Crystal.

In the midst of the emotionally charged encounter, The Tonight Show producer, Freddy Dart, opened the door with confusion on his face. Crystal reassured Dart that everything was under control, and Cosell confirmed his commitment to the show, willing to discuss any topic Crystal chose.

The show carried on, and when it was time for Cosell to make his entrance, he had composed himself. Crystal and Cosell engaged in a conversation about the upcoming NFL strike, but the sportscaster dismissed the topic, insisting on discussing something more current. Regardless of the subject Crystal proposed, Cosell seemed uninterested, displaying his immense ego.

To redirect the conversation, Crystal asked Cosell about his favorite call in all the different sports he had covered. This question sparked an extraordinary response from Cosell, as he launched into a theatrical recitation of various play-by-play calls, complete with hand gestures and dramatic flair. Cosell’s performance amazed Crystal, who found himself in awe of Cosell’s ability to dominate the conversation.

The interview reached a commercial break after the unforgettable moment, leaving Crystal impressed by Cosell’s showmanship. The story left Colbert and the audience thoroughly entertained, underscoring Crystal’s talent for storytelling and captivating an audience.

Billy Crystal‘s appearance on The Late Show with Stephen Colbert was a testament to his enduring charm and his ability to recall fascinating anecdotes from his extensive career. As one of comedy’s most beloved figures, Crystal continues to delight fans with his unforgettable experiences and his ability to bring joy to both the small and big screens.