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Crazy Awesome: William Todd from "Walmart Chemical Warfare," a man who committed 11 felonies in Nashville, Tennessee. Including, but not limited to, jacking a slaughterhouse, two cabbies, four people leaving a bar, a Canadian couple and ransacking a law firm. All in NINE HOURS. It's the frickin' Real LifeGrand Theft Auto!
Additionally, his use of "Doctorin' the Tardis" by The Timelords when he has to explain back-story. Sometimes he uses "Doctor Who on Holiday" a mashup between "Doctorin' the Tardis" and Green Day's "Holiday" from the American Edit mashup album.
To be fair, he doesn't seem to have many negative comments about the show itself or the more level-headed fanbase as a whole. He most likely wanted to address the people who take their obsession with the show too far.
Hilarious in Hindsight: Tara's rant about how juggalos will be the downfall of western society becomes even funnier if you happen to be reading Homestuck about a month later.
Just Here for Godzilla: There's a large portion of the viewership of Radio Dead Air that are only there for live WTFWWY, to the point where asking when it will start in the chat before its 11:30PM US Eastern start is now apart of the Drinking Game the regulars have. The regulars also enjoy lightly riffing about the "mass exodus" of people leaving the chat immediately once the show is done (some even leave before the sum-up is over).
Some new users that come only for WTFIWWY are often dismayed that 90% of RDA is music (primarily requests that skew towards the Alternative Rock side of things) and make their point of airing their dissatisfaction with this as loud as they can. These people are usually banned before WTF even starts. Bans are also apart of the Drinking Game.
Nightmare Fuel: Some of the stories featured are heavy on this. Notably in the 9-19-11 Live show, a story featured a man having an eel swim up his penis. Fully conscious. He even tried to pull it out while it was "burrowing" in. *shudders*
Squick: The stories featured on the show tend to be... kind of gross at best, and absolutely horrifying at worst.
Taken to Beyond the Impossible levels when somebody has sex with a dead squid. Which, as theorised by Nash, will spawn CTHULHU.