My childhood songs would have to be a combination of something ridiculously light and happy (maybe "Jolly Holiday" from Mary Poppins), something sporty and spunky ("Follow Me Boys"?) and something slightly poignant, like the reprise of "Belle" from Beauty and the Beast (because I was a daydreaming nerd as well as a tomboy.) And also the Anne of Green Gables soundtrack by Hagood Hardy will always remind me of my childhood and my mom, for some reason. But it's beautiful and melancholy and I love it.
Junior high... yikes. Is there a song that sums up the ugly stage of a seventh grader with the social awkwardness that accompanies a strange sense of confidence at that age? Hmm... well, that was the time I discovered Newsies so really any of those songs would at least remind me of that time, even if they don't quite encapsulate the weirdness of it.
Ah, high school. Actually part of junior high would apply here too, but at least the first half of high school would have to be one or more Taylor Swift songs... I remember when I first heard her music that I thought, "It's a good thing these songs weren't around when I was in 9th grade. How pathetic would I have been?" Probably "Teardrops on My Guitar" but more likely "You Belong with Me" would have been my anthem. (I'm not proud of that.)
Moving across the country when I was 15 (and what started off as "In My Own Little Corner" and something depressing- maybe "Rainy Days and Mondays"?) was a crazy thing... but it also put me in the middle of a lot of people I didn't know (and more importantly, who didn't know me... or my older sisters) so I kind of became this new, confident version of myself. I don't remember feeling terribly confident, but I remember having a lot of new friends and new experiences (playing softball (badly), singing my first solo (not quite as badly) that were so far removed from everything I knew on the West Coast that I felt like a different person. So, how about "I Have Confidence" (with the qualifier "sometimes) and "O, What A Beautiful Mornin'"? (That's how I felt about living in North Carolina by the end of it all.)
Ah! But then to move again! Just when I had gotten used to my great new life. Back to "In My Own Little Corner" (or, if I had been a typical teenager, maybe something angry by Avril Lavigne. Ha!) Of course, Georgia charmed me pretty quickly and I fell in love with living there, too. (It didn't hurt that that summer of '05 included a trip to Disney World/Universal Studios and several Braves games.) I'd have to say that summer and the next couple years would be represented by "Georgia on My Mind," "Tim McGraw" (yes, Taylor again... but only because the summer that song came out it was EVERYWHERE), and really any country music... I had never heard so much in my life until we moved to Georgia. (Braves games are represented by "Thank God I'm a Country Boy.") And I think all teenagers can be characterized by "The Age of Not Believing" from Bedknobs and Broomsticks.
My college experience is far too varied and would require an entire soundtrack of its own but starting with getting dropped off as a freshman, I'd have to go with the "Goodbye" song from Fox and the Hound (along with the weeping), then the rest would have to be represented by choir music because that's pretty much all there was (other than singing German and Italian for voice lessons which I'd rather not commemorate.)
Backing up a little to the summer after I turned 16, I fell in love with a skinny, blue-eyed boy from Goldsboro (he didn't fall quite as quickly, strangely enough!) but I felt lucky, very lucky, to eventually be dating him (still do!) and it would be impossible to narrow down a list of songs for him. Maybe start with "Impossible" from Cinderella, then "Puppy Love" by Damian McGinty, then probably some dramatic country song I liked at the time, then "You Are the Music in Me" from High School Musical 2 (again, I didn't say I was proud of all of these.) I'm sure we had what we considered "our song" at the time but am I a terrible person if I say I can't remember? Then maybe "Put Your Head on My Shoulder" by Michael Buble (scandalous!), "When God Made You" (one of our wedding songs) and "I Won't Last a Day Without You" by The Carpenters. And "We've Only Just Begun" by The Carpenters to represent our first year as clueless newlyweds.
Man... there have been so many crazy times since we've been married. (Mostly good crazy... and I don't mean constant fighting over whatever most newlyweds fight over. I was in school and Jonathan was teaching for the first time... we were too tired to fight! Those first couple years would be "The Bare Necessities" from The Jungle Book. =) I'd say change has kind of been a theme along the way, and dreaming, and coming up with new plans (that later changed, as is our way.) Again, I'd have to say "Strange Things" from Toy Story, "What's This?" from Nightmare before Christmas (ha!), and even though I wish I could say, "Hakuna Matata," it would probably something a little less relaxed. I'd throw in "I Dreamed a Dream" from Les Miserables if it's not too excessive.
But more recently... the Broadway Aladdin soundtrack ("A Million Miles Away" and "Proud of Your Boy"), "Santa Fe" from Newsies, "Houston" by Dean Martin =), "Glorious Unfolding" by Steven Curtis Chapman, "Baby Mine" from Dumbo, and really any other Disney lullaby there is (in anticipation of Baby M.) Also, overarching for the soundtrack of year 25, would probably be "Let It Go"... but then, isn't that on the soundtrack for all of America at this point? Oh, and through it all (at least the last five years), it's been Disney on Pandora, Michael Buble, Selah, Casting Crowns, and, always, the Psych theme song (a mood-lifter on even the worst days.)
You got all that, Amanda? (That's a long soundtrack.) For everyone else... now go play the game yourself. (If you don't have a talented pianist in the family it won't be as fun but just try.)
I don't know what the "song of year 26" will be but I'm anxious to find out! (Is there a song about growing old and forgetful? I'm thinking that might be a winner.)