"Fifteen" by 5 for Fighting reminds me of my sons growing up, especially the line, "15, caught between 10 and 20." It just resonates with me that teenage boys can be so grown up one minute and you can see the flashes of the men they're becoming, but then still be little boys the next minute.
"That's My Job" an old country song by Conway Twitty reminds me of my dad. I was always a "good kid" who ran away to Germany after my first year of college and married my teenage sweetheart who was stationed there. My mother just about disowned me, but my dad sent me letters and encouragement during that time. My husband (now ex) spent a lot of time in the bar on post where they played a lot of country music. I can just remember hearing that song and knowing my dad had my back, however misguided I was at the time.
https://www.youtube.com/watch?v=L7XK_zNq930