A song that reminds you of an event: Whiskeytown "Houses on the Hill"
I saw these guys at the Ranch Bowl in Omaha in the late 1990s. I'm not sure of the year, but it was on (a very drunk) Ryan Adams's birthday. They started the show with a Replacements song, and played a few songs before Ryan Adams declared that "it sucked, so we're going to start over." They replayed the Replacements song and when Ryan Adams immediately began the song again, Caitlin Cary stormed off the stage followed by the rest of the band.
Ryan Adams returned a few minutes later telling everyone that "they're pissed because I'm drunk." He then went on to play a 10 minute version of an early song of theirs, making up new words as he went along. I suppose it's a testament to his lyrical ability, because the lyrics weren't terrible. The band eventually joined him onstage and the rest of the show was great. There were two or three acoustic songs (including this one) at the end where Ryan and Caitlin sat on the edge of the stage and played acoustically and without microphones while the crowd gathered around. I had been in front of the stage for most of the show, so I was an arm's length away from them at the end.
Ryan Adams? Three feet away? With his acoustic guitar and fiddle accompaniment? Yep, it happened.