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Chewbacca’s pants are discussed in Episode #11 Hans Solo’s Dog.

The Talk Show with John Gruber is the longest-running of Benjamin’s Apple-oriented one-on-one shows.

His third broadcast was a roller coaster ride with a brain fired up on ADHD meds - and 5by5’s most-downloaded episode of all time.

Back to Work with Merlin Mann, a brilliant, eccentric Mac enthusiast who urges listeners to follow Buddha’s path to work-place enlightenment.

His on-air reaction: “What a bunch of dicks!” See Episode #11 The Mustache Guy. He did a show right after Rupert Murdoch and his team launched The Daily in a live webcast - his first glimpse of the men who run mainstream media.

Build & Analyze with Marco Arment, co-founder of Tumblr and creator of Instapaper, who brings a razor-sharp software engineer’s mind to bear on everything from iOS app design to brewing a perfect cup of coffee.

See Episode #3 The mouse is not a finger.

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My favorite episode was the one in which he makes the case - in an SAT-type analogy - that Apple’s Lion is to OS X as the original Mac OS was to MS DOS. Hypercritical with Ars Technica‘s John Siracusa, whose motto is that there’s no technology so perfect that he can’t find something to complain about.In addition to Gruber, one of the smartest and quirkiest writers covering Apple, there’s … Any subject that he and his co-hosts can’t dispose of in 60 to 90 minutes is simply pushed forward to next week’s show.

In stark contrast to the rapid-fire, deadline-driven pace of most cable news and drive-time radio, Benjamin gives the impression that his guests have all the time in the world - which in a sense they do. That Gruber, who does a weekly 5by5 podcast called The Talk Show, felt free to leap from a discussion of the latest Nielsen smartphone survey to why Chewbacca was permitted to wander through the George Lucas’ Star Wars series without any pants is one of the things that makes Benjamin’s talk shows so appealing. The co-host is Dan Benjamin, a Linux programmer turned talkshow impresario whose 5by5 Internet Broadcast network has become destination listening for hundreds of thousands of Mac and iPhone devotees. The guest is Daring Fireball‘s John Gruber, dean of the Apple (AAPL) bloggers.

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In the middle of a live broadcast discussing Twitter’s new president, Google’s (GOOG) Android market share and why Microsoft’s (MSFT) Windows Phone 7 is a terrible name for an operating system, the guest pauses to ask his co-host: “Speaking of well-hung Wookies, does this show have a sponsor?”