The Psychobilly Cadillac, which a fan in Tennessee actually built for Cash.
And Shel Silverstein wrote “A Boy Called Sue”.
I’d say that Harry Chapin wrote the most honest happy ending songs. The protagonists of “Sequel” don’t go back to being the young dreamers they were when they were dating; they’ve been scarred by their experiences, they’re battered by life, but they’ve gotten some wisdom and some strength. Likewise the little man of “A Better Place To Be” still has his empty job and lonely boardinghouse room, but he’s going to at least offer the barmaid, the big ol’ friendly girl, the same comfort that the lovely lady offered him. Chapin’s heroes get imperfectly happy endings.
Judy’s Turn to Cry has a happy ending for the singer and Johnny, but not so much for Judy. The Battle of New Orleans has a happy ending for Andrew Jackson, again, not so much for the British. The same holds for Timothy – a happy ending for all but one.
“Jackaroe” – she heals his wounds and they get married.
“Silhouettes”, if you count that as a story song.
Shel Silverstein’s “The Winner.”
Charlie Daniels’ “Ballad of the Uneasy Rider”.
Unlike many country music story songs Garth Brooks’ “Unanswered Prayers” has a happy ending. The middle-aged narrator meets the girl who’d broken his heart years earlier. He realizes at last that they were wrong for each other in the first place, and is glad he married someone else.
In a strange sense, Michael McDonald’s “What a Fool Believes” has a happy ending, but only because the song is about a fool who’s too blind to see that his beloved has just given him the brushoff!
The fool is happy, and think he still has a shot with her!
And in “Da Ya Think I’m Sexy,” the narrator and the woman he brought home get it on and then watch a movie. It does turn out that he is out of coffee, though, so perhaps that ending should be considered “mixed.”
Out of milk AND coffee, you mean. Unmitigated disaster. It’s like something off of Springsteen’s Nebraska album. Makes “When The Levee Breaks” sound like “Got My Mind Set On You.”
Decemberists - The Mariner’s Revenge. While not altogether happy tale, the protagonist gets his revenge on the debt ridden drunken mess that he’s been searching for all his life. At least, before he gets digested by a whale.
We fired our guns and the British kept a’comin.
But there wasn’t nigh as many as there was a while ago.
We fired once more and they began to runnin’
down the Mississippi to the Gulf of Mexico.
