Being a late-night TV host means dealing with some pretty big personalities. It can also mean giving in to unusual or bizarre demands, which Conan O'Brien learned about firsthand when he invited a dream guest on Late Night.
Getting guests on Late Night with Conan O'Brien wasn't easy in the early days. O'Brien was basically a complete unknown, and critics didn't portray the show as a place that any celebrity should be associated with.
But that changed as the years went on and O'Brien established himself as one of the best in the business. And Late Night's appeal to younger audiences gave Conan the freedom to request more guests he wanted to have on the show.
When Conan wanted the legendary Hunter S. Thompson to appear on Late Night, the notoriously elusive writer refused time and time again. However, Thompson finally agreed in 1997. But he had some lofty demands for O'Brien.
Thompson did not want to travel to New York City and sit down in studio at 30 Rock. Instead, he demanded O'Brien meet him at a farm for a remote segment that would involve shooting guns and drinking hard liquor.
According to O'Brien, Thompson probably thought the comedian would balk at the request and say forget it. Instead, O'Brien packed up a camera crew and met Hunter S. Thompson's demands.
The segment featured O'Brien and Thompson ordering drinks and guns from a makeshift bar in an open field. The pair took turns unloading on things like copies of Thompson's book, a teddy bear, and the NBC logo. Anyone hoping to see an interview must have been disappointed.
Things didn't get much better when Thompson finally arrived in studio in 2003. O'Brien did his best to get through the interview, but the one-of-a-kind author was his classic self. Then again, after you've shot machine guns and whiskey together, a chat on the couch doesn't seem all that exciting.