Songwriter Colin Meloy has characterized the song as a "protest song" inspired by the Iraq War. However, though it does attack elements of American foreign policy under George W. Bush (the lines "'Cause America can/and America can't say no/And America does,/if America says it's so,/it's so" in the chorus), "Sixteen Military Wives" focuses primarily on the news media and popular response to the war, particularly levying criticism at infotainment and the surface-level involvement of celebrities in public affairs.

Shot at Cleveland High School in Portland, Oregon, the video takes place at the fictional Barger Rothery Academy. Colin Meloy plays Henry Stowecroft, a student who represents the United States in the school's Model UN. Fed up with Jude (Nate Query), another student who seems to surpass him on every occasion, Henry goes after Carl (Chris Funk), a shy student who mostly keeps to himself, by initiating a campaign of harassment. Within the Model UN, the U.S. declares war on Luxembourg, the country Carl represents. Henry has his lackeys block Carl from using the bathroom, pelts Carl with crumpled paper projectiles, gets the lunch lady to deny Carl food service, and plants contraband in Carl's locker and then reports him to school authorities. Molly (Jenny Conlee) leads a revolt against Henry by recruiting the rest of the Model UN to perform a protest song during a meeting of the club. Henry, defeated, flees the meeting, and the video ends with him buried in crumpled papers thrown at him by his enraged classmates.

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