The first music I can remember my mom always listening to is Patsy Cline, I would listen to her sing "Crazy" all the time, it's burned into my brain. My mom loved those old school, epic heart breaking songs and this one will always be one that reminds me of her.
Whenever my family took road trips, which was often, both my sister and I would sit in the back and "sleep" and my parents would sit up front and listen to music and sing together. They always thought I was sleeping but I was usually listening while my sister used me as a human pillow. Frankie Valli and the Four Seasons was also something my mom knew she could play and my dad would sing. So many of these songs remind me of sitting in the back seat of my dad's car listening to my parents sing together but this one, this one was one of my dad's favorites.
For me, in my life, my high school years were defined by Fallout Boy's album "Under the Cork Tree" was the album that was my life. All my friends were just getting our driver's licenses, we were driving out of the school parking lot (entirely too fast) blasting this album, even when it was too cold to have the windows down, we did. This song reminds me of driving around in my best friends Volvo, cruising through town hoping to pull up to that cute boy in a Jeep, and pretending we looked cool smoking the cigs we stole from someone (smoking is BAD).
The number one song that has defined such a big part of my life, that I have these memories that bring tears to my eyes and literally makes my heart squeeze is the Beach Boys "Surfer Girl". My first concert was a Beach Boys concert and my family would go to see them whenever they were in town. My dad absolutely loved them and he was beaming every time we would go, even though we basically knew their whole set list.
My dad wasn't an overly affectionate guy, he would barely hold my hand in public, he hated me hugging him in public so to piss him off I would do it in front of his business friends so I knew he couldn't pull away without looking like a dick. But every single time we went to a Beach Boys concert and they played "Surfer Girl" he would pull me to my feet (we were usually on the lawn) and he would put his arms around me and dance with me. Every single time. Those are the moments, minutes, where I would just close my eyes and be the happiest little girl in the world.
p.s. There are too many NSYNC and Britney songs that have meant something to me to add