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big louise by scott walker
They're not about being any particular age (and I'm way past my late 20's!) but these songs about the passage of time and getting older helped me out: "I Don't Wanna Grow Up" by Tom Waits (I like the Ramones version too). "The Good Old Days" by Eels. "Do You Realize??" by Flaming Lips. "Fragments of Time" by Daft Punk.