| # | First aired | "The Wørd" | Studio guest | Introductory phrase | Prod#
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| 390 | May 1, 2008 | (no word) | James Kunstler | "I started my Kentucky Derby party early! I'm full of Juelp and I've got a gun!" | 4059
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| 391 | May 5, 2008 | Free Gas! | Carl Hiaasen | "Happy Cinco de Mayo! Remember, tomorrow is a great day to buy a used piñata!" | 4060
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| Included an Alpha Dog of the Week and a late-night dance off with a mysterious South Korean pop sensation who appeared from out of the mist...
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| 392 | May 6, 2008 | Collateral Friendage | Nathan Gunn | "Shouldn't it be: 'No we don't have any bananas'!? That's been bugging me for 75 years!" | 4061
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| 393 | May 7, 2008 | (no word) | Hasan Elahi, George Johnson | "You know what they say, when in Rome, get into a plane back to America!" | 4062
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| 394 | May 8, 2008 | (no word) | Garrett Reisman, Arianna Huffington | (no Statement of Truthiness) | 4063
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| 395 | May 12, 2008 | (no word) | Dr. Mehmet C. Oz | "The price of stamps rose a penny! Sweet, I just made 20 cents on my pack of "forever stamps"!" | 4064
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| Dr. Colbert introduces a new segment, Cold War Update to the heroes. More threats were discussed on the Threat Down.
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| 396 | May 13, 2008 | (no word) | Jennifer Hooper McCarty | "You put your left foot in, you take your left foot out! You put your left foot in and you shake it all about! Who knew restless leg syndrome was so much fun!?" | 4065
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| Dr. Colbert discusses a video of Papa Bear discovered on The YouTube.
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| 397 | May 14, 2008 | Declaration Of Warming | Laura Dern, Grover Norquist | "Give a man a fish; he'll eat for a day! Give him a sub-prime fish loan and you're in business, buddy!" | 4066
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| Dr. Colbert regretfully had to have another Who's Not Honoring Me Now segment.
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| 398 | May 15, 2008 | Jail Sweet Jail | Andrei Cherny | "Good things come to those who wait..." | 4067
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| Dr. Colbert celebrates "Happy American Craft Beer Week!", discusses Secret Time-traveling Nazi Muslims and dispenses financial advice with another edition of Stephen Colbert's Bears & Balls
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| 399 | May 27, 2008 | (no word) | Brian Greene | "We're starting summer hours here! Thank you and good night!" | 4068
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| Dr. Colbert recognizes Fleet Week, regrets gay marriage and watches Trailers That Are Destroying America all for the benefit of The Heroes!
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| 400 | May 28, 2008 | Brushback Pitch | Senator Claire McCaskill | "Tonight's show is brought to you by the number One and the letter Me!" | 4069
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| Dr. Colbert brings another segment of Cheating Death!
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| 401 | May 29, 2008 | (no word) | David Sirota | "Early to bed and early to rise makes you a loser! Let's party all night long!" | 4070
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| Dr. Colbert wags his judging finger and tips his complimentary hat, but America's Greatest Newsman goes intergalactic with an interview of an astronaut aboard the International Space Station!
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