5 songs.

Long before I had an iPod (but everyone else did) I would make mix CD's for my discman.  Usually it was some sort of mash-up of songs I had heard recently and liked, mixed with some older songs I had rediscovered.  Since I hated writing the titles of the songs on the discs themselves, I would label them based on when I made them or what the occasion was surrounding it, or, when I got real creative, a lyric from the first song on the CD.  It was a terrible organization system - many a person has flipped through my giant CD book, pulled out a random mix, and stated something like "What's on 'Florida Mix '03'?" (S Club 7, Whitney Houston, Disney covers and a little JC Chasez.)  But it was a system that worked for me, and, ultimately, attached lots of memories to a random playlist that I can recall the second I listen to it.

Because of this, choosing just five songs was really tough.  There are probably thousands of songs that I have a memory attached to.  Charlie will comment that, quite often, while we are driving, a song will come on and my immediate response is "oh, man, this song reminds me of _________" and then I go into a 20 minute story that means absolutely nothing to anyone else but me.  Sometimes, those memories aren't great ones, and I'd ignore a song for a long time because it was instant heartache.  (It took me a very long time to recover from "We Might As Well Be Strangers" by Keane, "Cautioners" by Jimmy Eat World, and "Dreaming With a Broken Heart" by John Mayer.)  But for the most part, one of my favorite things about music is how much it can transport you.  To instantly listen to a song and be sucked back to a point in your life you haven't visited in a while?  That's pretty cool.

"Springsteen" - Eric Church

This is one of those songs that not only has a memory attached to it, but also brings back a certain feeling.  Its that kind of song that you hear and you're like "whoa, this reminds me so much of being 17/18 and yet I just heard it for the first time at 24."  When driving cross country with my dad almost a year ago (crazy!) we listened to a lot of local radio stations through the midwest, and it was mostly country.  This song was very, very popular on the airwaves at the time, so we heard it often, but the one thing it reminds me of the most is Kansas.  Wide, flat, goes-on-forever Kansas, with its sweeping plains and the random gas station or farm you would pass every 20 miles or so.  While this song was playing, I watched a crazy thunderstorm literally roll in from the south, and knew I was approaching it miles before I was in it.  It was beautiful, awesome and a little bit haunting.

"Nothing Left to Lose" - Mat Kearney

I spent my first semester of college at Arizona State, in a single dorm room on the south end of campus, settled up right against a railway.  I also discovered this song right around the time I got there, and I took my iPod with me everywhere.  This song was on the Top 25 rotation for a very long time, and there's a line where he says "I can still hear the train outside my window" which always reminds me of the nights I'd fall asleep in that dorm room, hearing the train.  It brings me right back to that campus the second I hear it.

"Dreamgirl" - Dave Matthews Band

I was never a fan of this video but loved this song.  This was on heavy rotation the summer after my junior year of high school and makes me think of long, hot summers.

"Waiting in Vain" - Annie Lennox

This is one of my absolute favorite covers, from one of my favorite movies, Serendipity.  It also reminds me of my semester at ASU - I had my iTunes set to alphabetize by artist, so this was one of the first songs that would come up, and it was a great way to start the morning.

"Boston" - Kenny Chesney

Last but not least.  I've seen Kenny in concert twice, and being from Massachusetts and a little biased, I have always loved this song.  My favorite memory, though, is the last time I saw him at Gillette Stadium.  It had been drizzling all day, on and off, which made for a not-so-great tailgate.  By the time his set was half over, it was full on raining, yet when he started this song, surrounded by hundreds of thousands of Bostonians, the vibe totally changed.  I will never forget how amazing it was to be surrounded by great friends, singing along to this.