Penn Jillette is arguably one of the best guests Glenn has onto his show. The two are good friends and constantly debate over e-mail, even though they have wildly different opinions on a variety of topics. But their conversations always provide for an entertaining, intellectual and highly engaging debate. Tonight, Penn and Glenn talked about Penn’s optimism, the problem with tribalism and why MSNBC’s Lawrence O’Donnell wants to sit down with Glenn.

In the clip below, Penn kicks off the conversation by talking about why he remains optimistic despite the fact that it feels like the government is encroaching on individual rights and liberty.

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Penn told Glenn that MSNBC host Lawrence O’Donnell, a friend of his, actually would like to sit down for a private conversation and discuss some places where they agree.

“[O’Donnell] said, you know, ‘I would love to sit down with Glenn Beck and talk privately.’ Penn said, ‘We have a lot in common.’ And he went on and on like that, then said, ‘but you know, with our jobs and where we are it will probably never happen.’”

Glenn didn’t agree that their respective jobs meant they couldn’t talk, and lamented the idea that people who work in media focus so much on their jobs or ratings rather than honest conversations.

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And in this third segment, Penn and Glenn debate tribalism: