In an exciting and unusual segment on the famous talk show, David Letterman took to the streets of New York City to crown a new “Mr. September.” The competition was open to both men and women, with some exclusions for public figures and jockeys. As David read out the rules, he humorously mentioned the prohibition of using industrial solvents without adequate ventilation, adding a touch of David’s classic wit to the proceedings.

The prizes for the competition ranged from a sponge for the third runner-up to a Punky Brewster t-shirt for the first runner-up. However, the ultimate winner, Mr. September, received a special prize – the new Sam Harris single titled “Sugar Don’t Bite.”

With cameras located on 6th Avenue, David and his team went through the busy streets of New York City to find potential candidates for the title of Mr. September. The lively crowd in the audience played a participatory role, calling out potential candidates for David and his team to capture on camera.

Throughout the search, David interacted with the crowd, making humorous remarks and engaging with the people he encountered. From a guy in a suit to a young lady, David ensured a diverse array of candidates for the competition.

After the initial round of selecting potential candidates, David and his team reviewed the footage to narrow down the options. From the five preliminary candidates, they needed to choose two finalists who would compete for the title of Mr. September.

As the search continued, David expressed his desire to include a woman in the competition. And eventually, they found a woman in a blue and white polka dot dress who, along with a man in a denim jacket, became the two finalists.

With the finalists chosen, it was time for the audience to vote. Applause measured by an “unbelievably sensitive piece of equipment” would determine the winner. The anticipation built as David prepared to announce the results.

After tallying the votes, David revealed the winners. The man in the blue hat and glasses became the third runner-up, receiving a Today Show t-shirt. The man in the purple sweatshirt claimed the second runner-up position, earning a Punky Brewster t-shirt. And if the winner was unable to fulfill their duties, the woman in the blue and white dress would step in, receiving a lovely bear t-shirt.

Finally, the moment arrived to crown the new Mr. September. Eric Watson, who sported a denim jacket, emerged as the winner. Hailing from Coney Island in Brooklyn, Eric worked as a lunch deliveryman. His prize was the new Sam Harris single.

To celebrate Eric’s victory, Paul, the band leader, performed a special musical tribute. The night concluded with a thank you to the guests, emo Phillips and Gary Bucy, and an invitation for viewers to tune in the following night for another exciting episode.

This fun and entertaining segment on the David Letterman show highlighted his wit, charm, and ability to engage both the audience and passersby on the streets of New York City. By crowning a new Mr. September, the talk show brought unexpected laughter and excitement to its viewers.