In a recent episode of Conan O’Brien‘s talk show, the host revealed a bizarre and fascinating story involving one of his guests, Matt Gourley. Before getting into the details of the story, O’Brien mentioned that he had overheard Gourley talking about a previous job that seemed quite strange and intriguing.

According to O’Brien, Gourley explained that there was a man who had discovered a corporate loophole with an airline. This man figured out that if he paid people, like Gourley and his friends from their improv group, to fly legs of a flight, his company would accrue more mileage than it would cost to pay these individuals. It was essentially a mileage scam.

Back in the 1990s, Gourley and his friends were part of an improv group that was associated with a show on NBC called Quick Wits. This show was syndicated and aired after Saturday Night Live, but it wasn’t widely known. The producer of the show, who was also running this mileage scam, would pay Gourley and his friends to do multiple roundtrip flights in a day to various destinations.

Gourley and his friend chose San Francisco, while others in the group opted for places like Vegas and Arizona. They would fly from LAX to San Francisco three times a day, getting off the plane and immediately getting back on the same plane. The flight attendants would give them strange looks, as if they were drug mules or something.

The producer would hand them something that would put them to sleep on the plane, and when they woke up, they would feel something in their bottom. Gourley joked that it happened most nights, but it was all in good humor.

However, this mileage scam didn’t go unnoticed by the airline. Eventually, they discovered what was happening and got into a big argument with the producer. There was a quota amount that each person had to meet, and if they didn’t meet it, they had to pay a penalty to the producer. Thankfully, the airline settled with the producer, and Gourley and his friends didn’t have to finish their quotas.

Gourley went on to mention that the producer wrote a self-published book about the scam, which may be available on platforms like Amazon. However, it seems that this incident didn’t lead to any significant career success for the producer in showbiz.

As the conversation continued, O’Brien and Gourley reminisced about other odd experiences they had in their respective careers. They discussed different projects they worked on, including a video that Gourley did for the National Association of Music Vendors. It involved improvising as a salesman in a video teaching people how to sell musical instruments.

Throughout the discussion, they joked about embarrassing moments and shared laughter. O’Brien mentioned that he would love to see Gourley on the show Quick Wits, but they doubted if it would be available on platforms like YouTube.

The episode concluded with O’Brien suggesting a segment where they all bring in their most embarrassing moments captured on tape.

Overall, this lively and entertaining conversation on Conan O’Brien‘s talk show provided a glimpse into the unusual world of a mileage scam and the absurdities of the entertainment industry. Fans of Conan O’Brien, chat shows, and celebrities like Matt Gourley will definitely find this episode entertaining and worth watching.