Tear Jerker: "Weird Al" Yankovic

Yes, even this comedy musician is not immune to creating songs that can (unintentionally) move one to tearseven if they were intended to be humorous.
  • "Skipper Dan", amid the theater and Disney references, is the completely miserable tale of a man forced to give up his dream of being a great actor just to make ends meet. And each line is more depressing than the next, especially the way he near-tearfully says "What have I done with my life?" on the bridge,
  • Not only is the tune for "You Don't Love Me Anymore" 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.
    • The way the synthesized stringd swells at the end, after he's been left for dead in a drainage ditch, gives one the mental image of the narrator ascending to heaven as he still pines for this woman who despises him.
  • "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.
  • YMMV of course, but the Reality Subtext of the general disappointment of The Phantom Menace and the specific way it ruined Jake Lloyd's acting career, coupled with the elegiac tone of the song it parodies has given "The Saga Begins" a mournful quality. Just try listening to the last chorus while reading about how Lloyd eventually destroyed all his Star Wars memorabilia... (it's unknown if he actually he did destroy his memorabilia, but it has been confirmed that he does not hate Star Wars after all that)
  • Don Pardo's tongue-lashing on the bridge of "I Lost On Jeopardy" can be a real spirit-breaker, especially since he says all of the following in his cheery announcer voice.
    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 is similarly a bit of a downer.
  • 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.
  • "Mr. Frump in the Iron Lung" can hit close to home for anyone who visits a barely responsive friend or family member in the hospital, particularly the end where Mrs. Frump dies.