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"Skipper Dan", amid the theater and Disney references, is a surprisingly sad tale of a man whose dreams of success and fame were shattered by reality, leaving him in an endless rut working day to day to pay the bills and deal with his depression. Not nearly as tragic as other examples on this list, but far more likely to hit close to home.
"You Don't Love Me Anymore" might be far worse. Not only is the music genuinely sad, but it's about his girlfriend's attempts to murder him. The lyrics are intended to be humorous, but occasional lyrics like "you're still the light of life" and "my scars are all healing but my heart never will" implying the singer still loves the subject of the song might still bring tears to one's eyes.
"One More Minute" is a song about a man describing all kinds of painful things he'd rather do than spend one more minute with his ex, who is now seeing someone else; it's obvious, though, that all the painful things he's describing are how he feels seeing her with someone else and the only thing in the world he wants is to have just one more minute with her.
I'd rather tear out my intestines with a fork than watch you going out with other men...
The Darker and Edgier version of "The Night Santa Went Crazy" ends with Santa's brains blown out on the pavement - considerably darker than Al's usual fare, and especially hard-hitting for anyone who heard the version where Santa goes to prison.
"I lost on Jeopardy!" is a song by Weird Al Yankovic which is a parody of The Greg Kihn project: Our love's in Jeopardy! It's about him as a contestant who was competing with a plumber and an architect (who both have PHD's). Art Fleming (the Trebek version wouldn't debut until a few months later) gave out the answers but Weird Al did not respond the correct question. As a result, He did not win any prizes on Jeopardy! And everybody got mad at him for losing on Jeopardy! The crew member took Weird Al out the studio and toss him into the car (Who the driver is Greg Kihn) and was driven away.
Don Pardo: That's right, Al. You lost! And let me tell you what you didn't win! A 20 Volume set of the Encyclopedia Internationals, A case of Turtle wax, And a years supply of Rice-A-Roni, A San Francisco Treat. But that's not all, You made yourself look like a jerk in front of Millions of people. And you brought shame and disgrace for your family name for generations to come. You don't get to come back tomorrow. You don't even get a lousy copy of our home game. You are a complete loser!
The video for "TMZ" can have this effect. The video shows a famous woman being haunted no matter where she goes by a picture of her own rear, which in itself is funny. The song, however, is actually a pretty bitter criticism against paparazzi journalism, and near the end of the video, the starlet in question gets this strange, dead look in her eyes as she just stands still and lets everyone photograph her, looking like she is more or less accepting her fate. Thankfully, the video continues and ends with her getting revenge on the photographer that took the picture, but that one moment can hit hard.