On a recent episode of the renowned talk show 'David Letterman', staff member and segment producer Sarah Connell reflected on her 12-year tenure at The Late Show. Sarah began as an intern in 2002 and gradually worked her way up to talent assistant, talent coordinator, and eventually segment producer.

Sarah vividly recalls her first day as an intern, where everything felt brand new and surreal. She was amazed to see Biff Henderson, whom she initially mistook for a character, actually serving as the stage manager. This exemplified the unique dynamic of the show, where staff and crew members were included in comedic bits. Over the years, Sarah had the privilege of participating in several of these humorous sketches, including the nerve-wracking experience of performing one where the punchline involved surprising Matt Damon, who was sitting in the audience.

One of Sarah's favorite aspects of being a segment producer on the show was working with various celebrities. She particularly enjoyed collaborating with Steve Martin, taking a humorous jab at Sarah Palin's political stint, and playing the daughter of Martin Short. Sarah recalls filming the latter during a blizzard, with paparazzi lurking in the trees. The intense media attention occasionally made her question whether she was cut out for show business.

Reflecting on memorable moments with guests, Sarah reminisces about Courtney Love requesting to wear her Late Show t-shirt during a rehearsal, only to change her mind mid-performance, resulting in an unexpected topless episode. Such incidents made Sarah contemplate the unpredictable nature of her job.

Sarah also recounts instances when David Letterman's quirky humor took unexpected turns during interviews. For instance, when hosting celebrity guests, David would sometimes steer the conversation away from their intended topics, focusing instead on trivia like topography or geography. This left Sarah questioning whether she should begin asking guests more unconventional questions during pre-interviews.

The article also delves into encounters with political figures like Donald Trump during his pre-presidential days. Michael Cohen, Trump's former lawyer, once called the show in a fit of rage, berating Sarah over speakerphone, completely unaware that he would later cross paths with her in the hallways of 30 Rock.

Notable mentions are made of Jay Leno and Oprah Winfrey, who made memorable appearances on the show. Additionally, Sarah recalls the excitement of orchestrating a grand entrance for Madonna involving the New York Rangers carrying her out on hockey sticks. And during Selena Gomez's guest appearance, Sarah cleverly devised a way for David to humorously reference making Justin Bieber cry without causing discomfort.

Sarah's journey on The Late Show was filled with ups and downs, unforgettable moments, and encounters with various celebrities from different walks of life. Through her anecdotes, it becomes evident that working in the entertainment industry brings both excitement and unpredictability. As Sarah Connell bids farewell to The Late Show, her stories serve as a testament to the lively and entertaining nature of David Letterman's iconic talk show.