| # | First aired | "The Wørd" | Studio guest | Introductory phrase | Prod#
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| 402 | June 2, 2008 | Media Culpa | Jon Paskowitz | "I saw Sex and the City! Spolier Alert: she picks the Vivienne Westwood dress!" (mouths: "Oh my God!") | 4071
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| Dr. Colbert describes to America how powerful his prayers are!
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| 403 | June 3, 2008 | Unhealthy Competition | George Will | "Time flies, especially since I built a clockopult!" | 4072
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| Dr. Colbert declares his guest George Will a formidable opponent!
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| 404 | June 4, 2008 | (no word) | Sir Salman Rushdie | "Today is the first day of the rest of your life, and it's already 11:30! What a waste!" | 4073
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| Dr. Colbert speaks with a fellow Libertarian, Bob Barr and discusses The Lost O'Reilly Tapes!
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| 405 | June 5, 2008 | Oh, The Places You'll Stay | Pat Buchanan | "I regret that I have but one life to give! I WANT MORE LIVES!" | 4074
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| Dr. Colbert discusses America's eventual dominance in Timber Sports on another edition of The Sport Report!
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| 406 | June 9, 2008 | If At First You Don't Secede | Phil Weiss | "I always say, if you can't beat 'em, report them to Homeland Security; they'll beat 'em for ya!" | 4075
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| Dr. Colbert discusses infidelity with his guest, Phil Weiss
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| 407 | June 10, 2008 | (no word) | Alan Rabinowitz | "I'm Stephen Colbert, the most trusted name in the name of my show!" | 4076
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| The Prescott Group brings another school movie, "The Elitist Menace Among Us"
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| 408 | June 11, 2008 | U.S. Airweighs | David Hajdu | "The heat wave is over, but I'm still smokin'!" | 4077
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| Dr. Colbert discusses the comic menace with his guest, David Hajdu
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| 409 | June 12, 2008 | (no word) | Dr. Dickson D. Despommier, Winona LaDuke | "Tony Awards, it's not too late to revise your list of nominees! Kapow!" | 4078
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| Dr. Colbert reveals the first entry in his newest greenscreen challenge, Stephen Colbert's Make McCain Exciting Challenge! He also received $24 for the island of Manhattan from guest, Winona LaDuke and mediated another Hollywood slap fight!
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| 410 | June 16, 2008 | Ploy-cott | Kenneth Miller, REM | "Have I told you lately that I love me!?" | 4079
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| Dr. Colbert remembers guest, Tim Russert
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| 411 | June 17, 2008 | (no word) | Neal Katyal, Jonathan Zittrain | "Mark my words! Serious, Mark, where's my words!? I need my script!" | 4080
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| Dr. Colbert balanced his discussion on the latest in Timber Sports news with another edition of The Sport Report with nerd talk with his guest, Jonathan Zittrain!
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| 412 | June 18, 2008 | Lexicon Artist | Junot Diaz | "This is the dawning of the Age of Colbertius!" | 4081
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| Dr. Colbert revealed more words to The Heroes and engaged in more nerd talk with guest, Junot Diaz!
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| 413 | June 19, 2008 | (no word) | Bishop N.T. Wright | "Beauty isn't in the eye of the beholder! I've checked there's nothing in there but veins and goo!" | 4082
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| Dr. Colbert talks God with an Anglican, Bishop N.T. Wright and cookies with a monster! In addition, he brings more entries in his Stephen Colbert's Make McCain Exciting Challenge and did he mention he won another Peabody!?
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| 414 | June 23, 2008 | Black & White | Barbara Ehrenreich | "Guests of The Colbert Report stay at the luxurious Crash With A Friend!" | 4083
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| Dr. Colbert marks the one year anniversary of his near-tragic wrist injury with generous tips and wags!
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| 415 | June 24, 2008 | Beep | Will Smith | "I promise to deliver the truth in the next thirty minutes or it's free!" | 4084
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| //Summary
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| 416 | June 25, 2008 | (no word) | Paul Goldberger, Neil DeGrasse Tyson | "What do I want!? My own show! When do I want it!? NOW!" | 4085
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| Tonight's guest, Neil DeGrasse Tyson will make his fifth appearance, a record for nailings!
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| 417 | June 26, 2008 | (no word) | Robert Wexler | "I'm about to take two weeks off! You know what that means!? Fresh Injuries!" | 4086
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| //Summary
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