| # | First aired | "The Wørd" | Studio guest | Introductory phrase | Prod#
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| 1 | October 17 | Truthiness | Stone Phillips | "Open wide, baby bird, because mama's got a big, fat nightcrawler of Truth." | 101
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| Gravitas-Off versus Stone Phillips; Colbert salutes Peter Mayhew's US citizenship with a Chewbacca figure.
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| 2 | October 18 | Bacchanalia | Lesley Stahl | "Put some pants on, America. The Truth is knocking at the door." | 102
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| Part one of "Better Know a District" with Captain Jack Kingston (R) of Georgia's 1st District; First All You Need to Know.
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| 3 | October 19 | Disappointed | Fareed Zakaria | "Strap yourself in and flip the switch, 'cause you're about to get a Truthocution." | 103
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| First "Tip of the Hat, Wag of the Finger"; First "Stephen Settles the Debate" (Whales and Cod vs. Eskimo Hunters and Seals); First The Inbox, where Stephen reads e-mails from viewers.
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| 4 | October 20 | Love Handles | Jim Cramer | "Stop operating heavy machinery, because you're about to take two maximum strength tablets of Truth." | 104
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| First appearance of Russ Lieber; Stephen replaces the U.S. Constitution with a framed credit card offer; Lisa Loeb has a cameo, singing a few bars of "Stay (I Missed You)"; First Un-American News.
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| 5 | October 24 | Pussy | Lou Dobbs | "It's time to jump down, turn around and pick a bale of Truth." | 105
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| First Out-of-Context Interview, with Kay Bailey Hutchison; First Appearance of "Bring 'Em Back or Leave 'Em Dead," featuring Torquemada, Charles Darwin and Dave Thomas; a sequence on positive mugshots, in honor of Tom DeLay's arrest.
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| 6 | October 25 | Overrated | Greg Behrendt | "I swallowed 20 condoms full of Truth and I'm about to smuggle them across the border." | 106
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| Stephen tells the truth about Rosa Parks; Introduces his black friend Alan; First mention of his undying hatred toward bears; Took calls from listeners for the first time; first appearance of Yet Another Day, the Colbert Report morning show.
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| 7 | October 26 | Perspective | Neil deGrasse Tyson | "Strike up the klezmer and start acting like a man. You're about to have a Truth Mitzvah." | 107
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| Introduction to Stephen's self-published Sci-fi novel Alpha Squad 7: Lady Nocturne: A Tek Jansen Adventure; First appearance of "The Pulse," where Stephen plays a video of one of his fans asking him a question. Today's included How is the weight of paper determined? and What's your favorite Jay-Z Song? (Stephen listed his top 20).
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| 8 | October 27 | Quitter | Jeff Daniels | "Put on the Sade and spritz on some musk. I'm gonna Truth you all night long." | 108
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| Part two of "Better Know a District" with Barney Frank (D) of Taxachusetts's 4th District; Harriet Miers added to the Bookshelf of Broken Dreams.
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| 9 | October 31 | Alito | Monica Crowley | "Shave off your body hair and put on your bike shorts. You just grabbed the yellow jersey in the Tour de Truthiness." | 109
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| Second Out-of-Context Interview, with Patrick Fitzgerald; Stephen Settles the Debate: Ramadan vs. Halloween; Placed Rock and Roll nativity scene on his bookshelf to celebrate the end of "Rocktober."
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