The Wreck of the Edmund Fitzgerald

From OAPedia.com

"The Wreck of the Edmund Fitzgerald" is a song by Gordon Lightfoot about the sinking of a freighter on Lake Superior in 1975. It led to one of the most famous Opie and Anthony bits on June 3, 2005 where O&A began goofing on the song when it came up in conversation. O&A goofed on how long the song seemed to run, and on its inclusion of minute details about the ship and its wreckage, with Anthony doing a Gordon Lightfoot impression the whole time. Part of the bit also involved playing a portion of the song, leaving it alone, and then returning to the song much, much later to find that it's still playing (which was repeated when they goofed on the song "American Pie" months later).

The bit was also noteworthy in that it took place during one of the worst shows in O&A history, where nothing else about the show seemed to go right. Opie has stated since then that when he thinks of that day, he doesn't think of the bad stuff that happened - he only thinks of the great "Edmund Fitzgerald" bit.