- "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 to mention the music video for "Skipper Dan" too. We see Dan's daily routine preparing for his job whilst flashing back to his past whether it is graduating from Juliard, playing Romeo in his high school play, getting a standing ovation for his role in Cat On A Hot Tin Roof and singing autographs at the stagedoor, daydreaming about being on the Reservoir Dogs poster as well as a vision of his grandfather's spirit looking at him ashamedly. The kicker comes near the end of the video as we see Dan and the actress who previously appeared in the Cat In A Hot Tin Roof scene mime shooting each other in the head proving that this situation can happen to anyone, not just Dan. The video ends with Dan posing for photographs whilst holding an empty smile and a borderline Kubrick stare before cutting to black.
- 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. That is, if you ignore the 10 seconds of noise that comes later.
- The way the synthesized strings swell at the end, after he's been left for dead in a drainage ditch, sounds as if he's 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 year's supply of Rice-A-Roni, The San Francisco Treat. But that's not all! You also 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're a complete loser!
- The video is similarly a bit of a downer.
- The video for "TMZ," in which a famous woman being haunted no matter where she goes by a humorous picture of her own rear, which in itself is funny. Like the song itself, the video is 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 Dog Bites Back at the end.
- While it's intended as Black Comedy, anyone who visits a barely responsive friend or family member in the hospital might have a hard time listening to "Mr. Frump in the Iron Lung," particularly the end where Mr. Frump dies.
- Hearing Al talk about the 2004 death of his parents — yep, both of them, at the same time, due to carbon monoxide poisoning — is especially heart-wrenching, especially when he called the experience "the worst thing that's ever happened to me" in an interview years later. He went on to say that while common sense dictated that he would eventually have had to go through losing his parents, he didn't expect it to be as sudden and as swift as it ultimately was.
- What likely made it worse for Al at the time is that he got the news an hour before he was going on stage during one of his tour stops. No one would have blamed Al for cancelling the show or cutting the tour short after that, but Al insisted The Show Must Go On and completed the tour, only then returning to be with his family.
Tear Jerker / "Weird Al" Yankovic
Yes, even this comedy musician is not immune to creating songs that can (unintentionally) move one to tears — even if they were intended to be humorous.