Late Show with David Letterman Season 14 Episode 39 Rosie O'Donnell, Lady Sovereign

In this episode of the Late Show with David Letterman, the host welcomes two guests from very different walks of life: comedian and talk show host Rosie O'Donnell and British rapper Lady Sovereign.

David Letterman kicks off the show with his usual monologue, poking fun at current events and making witty observations about the news of the day. He then introduces Rosie O'Donnell as his first guest of the evening. O'Donnell, known for her outspoken and often controversial opinions, chats with Letterman about a range of topics, from her new talk show to her thoughts on politics and the state of the world today.

Throughout the conversation, O'Donnell displays her trademark wit and humor, making quips and observations that crack up the audience. She also gets serious at times, discussing her work as an advocate for children and addressing some of the criticism and controversy that has surrounded her over the years.

After talking with O'Donnell, Letterman welcomes his second guest, Lady Sovereign, a young rapper from the UK who has been making a name for herself on the hip hop scene since the early 2000s. Although Lady Sovereign is often associated with the grime genre of rap, which originated in the UK, she tells Letterman that she doesn't like to be pigeonholed into any one category.

During her interview, Lady Sovereign talks about her upbringing in a low-income area of London and how she got into music at a young age. She also discusses some of the challenges she has faced as a female rapper in a male-dominated industry, and how she hopes to inspire other young women to pursue their dreams.

At one point in the interview, Lady Sovereign mentions that she is a big fan of David Letterman and has been watching his show since she was a kid. Letterman seems genuinely touched by this and tells her that he's honored to have her on the show.

Throughout the episode, there are also plenty of funny and entertaining segments, including the famous Top Ten List, in which Letterman counts down a humorous list of ten things related to a particular topic. In this episode, the topic is "Rejected Olympic Sports", and the list includes such gems as "Wishful Thinking" and "Synchronized Sweating".

Overall, this episode of the Late Show with David Letterman is a fun and entertaining hour of television, featuring two very different but equally fascinating guests. Whether you're a fan of Rosie O'Donnell's outspoken humor or Lady Sovereign's edgy raps, there's something here for everyone to enjoy.