What, no mention of Billy, Don’t Be A Hero? :rolleyes:
I’d go with Momma Told Me Not To Come or Spill The Wine, but the first song I thought of was Ode to Billy Joe.
I think the Dylan songs are the cream of the crop.
Lily, Rosemary, and the Jack of Hearts Rich cast of characters, enough gaps in the story to make us think a bit for ourselves.
Black Diamond Bay Now a bit dated with references to the Soviet ambassador and Walt Cronkite but the varying reactions to the slowly developing certain death are interesting.
*Brownsville Girl * On his more underrated pieces. I love the style of going back and forth from a speaking voice to singing voice
Romance in Durango Another great story from the prime of his career
*Senor * Love the imagery and the building tension.
Another one that’s in my Top Ten – which, based on this thread’s suggestions, may now be a Top Twenty! 
We could go back to the cheesy Running Bear.
A minimalist classic, The Nails - 88 Lines About 44 Women.
A maximalist classic, Jaime Brockett - Legend of the USS Titanic.
Great thread. And thanks for the links. I have been introduced to many Story Songs.
I need to be in the mood for these songs, because they aren’t background music. Ya gotta listen.
One not mentioned is Harry Chapin’s Mr. Tanner.
https://www.youtube.com/results?search_query=mr.+tanner+harry+chapin&spfreload=10
Caution: Its a tear jerker!
Here’s another good one from Waits: “Burma Shave”.
One that’s very recent (2008) is Sometime Around Midnight.
The funny thing is that it’s barely a song. It’s more of a story told against music in a singing voice. No chorus or hook or anything.
Less recent is “Detachable Penis”… 
A good one: Guy Clark - The Guitar
I totally love that song. I'm glad I'm not the only person here who's heard it.
In any case, I thought it was 142nd (“141 was faster than he, but Irving was looking for 143”).
My favorite story song, though, has to be “Alice’s Restaurant”: https://www.youtube.com/watch?v=m57gzA2JCcM
This is another good one by my favorite folk singer: https://www.youtube.com/watch?v=wgXfvCNb6VQ
And, of course: https://www.youtube.com/watch?v=3i0DMbCKnAg
I think rap is a must if you’re going to discuss story songs (unless you’re using a definition that excludes “rap” from “songs”). Slick Rick’s Children’s Story is the best example, but virtually every rap act/group has one or more story songs in their repertoire.
Complex has a list of the top 50 storytelling rap songs. If you like rap, there are a lot of really good tracks on that list.
Give the guy his due! He was the 142nd fastest gun in the West.
For those unfamiliar, The Ballad of Irving is a - possibly now politically incorrect - tale of a Jewish cowboy/gunslinger.
Mind you, it was written and performed by Jewish entertainers … :rolleyes:
OOPS!
Looked for a response before I posted and missed this one!:smack:
In “City of New Orleans,” the train is the narrator–sorta like Thomas the Tank Engine.
How about those Kenny Rogers tunes “Lucille,” and “Ruby (Don’t Take Your Love to Town)”?
ETA: Irving, had a son named Seymour, but that song is nowhere near as entertaining as “The Ballad of…”
I disagree. The lyrics of the second verse make it obvious that the point of view is a passenger; trains don’t generally play cards or share a bottle.
No one’s mentioned this one. “Ringo” by Lorne Greene.
https://www.youtube.com/results?search_query=ringo+lorne+greene
On this subject, I’ll throw in Jim Stafford’s “Cow Patty” - hilarious!
I dis-disagree. The train is commenting on the behavior of his passengers–there is no identifying pronoun in that verse.
Which reminds me of “One Tin Soldier”. Those of “a certain age” will know why. 
Shakes tiny fist at Kayaker
Second submission…
Steve Earle Ben McCulloch from the Train A Comin’ album put out right after his release from prison.