Whenever I hear “Time Passages” I INSTANTLY flash back to a trip to NY I made with my family when in my early teens. We got on the train in Westchester County to go into the Big City and there were two cute, well dressed, young gay guys chattering away ahead of us. I felt such a stab of envy! There they were, happy, free as birds, off to what kind of adventures, and I was stuck schlepping around department stores all day with my bitch of a mother.
I associate those Al Stewart songs with the time I worked for the shipping company that distributed vinyl for GRT/Janus Records. We sent out thousands of boxes of “Year of the Cat” in the fall of '76. My room mate ripped off a case and gave out albums to all his friends; I called him on it, which resulted in a huge shouting match, him getting fired, and me needing a new room mate.
“Fire & Rain” James Taylor
Think I know what you’re getting at about “Baker Street” & “Under the Milky Way” though. Both very evocative.
A song I had totally forgotten about: “Book of Love” by Peter Gabriel. I heard that song this weekend… and I almost started to cry. It’s such an emotional song.
Sigur Rós - Glósóli
Baker Street sends me right back to being about 4 years old and first taking notice of songs on the radio (a local Top 40 AM station in all its mono glory). It’s always summer. 
Magical song, that one.
Looking forward to listening to all the songs in this thread.
For me the one is the recording of the shapenote hymn Idumea from Cold Mountain. (To be accurate I think this is not from the Sacred Harp but is a modern shapenote arrangement of a folk song. But, details, details.) Raw and gorgeous.
Wow, great examples everyone. Thanks for adding links to the more obscur ones, as I’d otherwise probably never have the pleasure of hearing them.
I just remembered another one: " Sunny Came Home " by Shawn Colvin. For anyone not familiar it’s the story of a woman who’s plotting to burn her house down. It’s never explained what made her that way but you really get a visceral idea of just how unbalanced she is.
The mandolin is so haunting and for me really conveys the title character’s loneliness and then the chorus is upbeat and suggests her tenuous grasp on sanity. At the start of the bridge(?) she sings in a kind of a whispery voice as “Sunny” starts to put her plot in motion
“. . .get the kids and bring a sweater. dry is good and wind is better” then rises to the final chorus and ends with those same haunting mandolin notes that are so perfect for the end of a tragic story.
Now that I’ve subjected you to more than you’d ever want to know about this song, shall I take a stab at “Ode to Billy Joe” ?
Richard Thompson’s Woods of Darney - A love story, a ghost story and a war story, all in under eight minutes.
Meet on the Ledge. Oh God, Meet on the Ledge… “Too many friends who tried, blown off this mountain by the wind.” - How they can get through it each time without breaking down completely, I don’t know. There’s always plenty of tears in the audience.
Never Any Good - Martin Simpson. A son’s ‘warts and all’ tribute to his father.
Don’t You Want Me Baby, Tainted Love, and Werewolves of London were on constant rotation in the student center cafeteria when I was in college. I cannot emphasize the word “constant” strongly enough. They may have been the only three songs on the jukebox.
Someone Saved My Life Tonight was at its peak the summer we drove from Ohio to Maine. And there was ONE radio station that would come in, and that was the ONE song they were playing. I hear that song, I think Aroostook, Maine.
As a sucker for nostalgia, I’m quite susceptible to songs that recall, with fondness and sadness at the same time, childhood and adolescence, or simpler times long gone by. Bob Seger really evokes those feelings with “Main Street”, with that sad, wailing guitar, and with “Against the Wind.” “Wish I didn’t know now what I didn’t know then”- tell me about it.
Another highly evocative tune is also, in my view, the saddest song ever: “What Sarah Said” by Death Cab for Cutie. It pretty much makes me feel what I imagine it’s like to be in a hospital waiting for someone you love to die. For those not familiar with the song, we don’t know who Sarah is, exactly, but what she said is “Love is watching someone die.” Devastating.
It’s cool to see the Al Stewart love in this thread.
“Defying Gravity,” from Wicked, evokes the rush of freedom, of breaking constraints, especially when Elphaba sings, “So if you care to find me… look to the western sky…” Before I ever saw it staged, I was desperate to see it staged, wondering how the staging would capture that exhilarating feeling.
“The Fall of Saigon,” the duet as Chris and Kim relive what happened to force them apart, just stomps my heart with the poignant hopelessness of what they were experiencing. When Kim is outside the Embassy desperately thinking “Please, Chris, no one sees, I am lost here, find me please,” and at the same time Chris is frantically calling her, thinking, “Please, Kim, hear the phone, I can’t get there, please be home…”
And from the opera that gave birth to that source material: the music when Cio-Cio-San stabs herself (“Con Onor Muore”) is heartbreaking, every single time I hear it.
Echolyn’s debut album has several songs like this, most notably “The Velveteen Rabbit.” One of the greatest albums of all time, IMO, but long out of print.