Favorite song: Wagon Wheel (Old Crow Medicine Show version)
Memory: Seeing it live at a small bar last year. I wasn't sure if I'd be able to make it so instead of the $30 ticket I had to pay $80 on a re-selling site. My roommate went to the library to print it for me and met me in line. The guy in front of me had an extra ticket so my roommate got in for free (then bought the guy a drink as a thank you, so what, like $7?)
At the time I first fell in love with the song I had a strong desire to move to North Carolina, and the song is centered around the narrator hitchhiking down the east coast to Raleigh, which really struck a chord with me. I also love that the original version by OCMS is very raw and unpolished; they're very talented but some people hate the singer's voice. I personally love its raw authenticity.
An extra little bit is that the refrain was written by Bob Dylan. Two of the band members found a vinyl of unfinished Dylan songs in a record shop, wrote the lyrics, and spent ten years playing it on street corners before recording it. When they contacted Dylan for permission he said he'd adapted it from Arthur Crudup, who had adapted it from "Rock Me Baby" by Big Bill.
About 100 years from the original bits from Big Bill (and with some significant changes made along the way) it became a #1 country song when Darius Rucker covered it (though I hate that version)