In the August 14, 2013 episode of the Daily Show, John Oliver discusses the future of newspapers, technology, and sport with Regis Philbin.

The episode begins with John Oliver talking about monetary difficulties newspapers have faced over the last ten years. It is expensive to create and sales have dropped dramatically. Despite this difficulty, The Washington Post sold to the Amazon Chairman, Jeff Bezos. One of the reasons for the purchase is that Bezos’ fortune is so large that purchasing The Washington Post will only put a small dent in it. This purchase will allow him to experiment with the medium. Apparently rich men purchasing newspapers has been happening. Oliver then brings on John Hodgeman as the resident deranged billionaire. Hodgeman wants to do something similar and has bought the Washington Penny Saver. In order to appeal to readers, he will be printing it in three versions: liberal, conservative and cat video enthusiast. He will also help pay for it with product placement. Oliver is worried that the news will become playthings for the rich, and Hodgeman is looking forward to it.

Oliver also discusses the news of a proposal for transport that would travel 400 mile in half-an-hour, the hyper loop. It is a capsule in a long tube, like the vacuum canisters that used to be in all of the banks. Elon Musk has invented many items. Oliver wants it explained, but no one in the media will. Even Musk does not explain it. He also will not be building it. He says he does not have time for to build it and hopes someone else will.

The guest for this episode was Regis Philbin. He has moved to hosting a sports show on Fox Sports 1. Oliver and Philbin spend most of the interview discussing sports and why people love them.