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  • Harsher in Hindsight: Plenty of episodes had the happy or otherwise hopeful ending wind up as this. Such examples include Vanilla Ice's episode (where it came out that there was domestic violence in his seemingly happy marriage that eventually led to their divorce) and Madonna's episode (where the Updated Re-release had her declaring her love for director Guy Ritchie and the two not only underwent a bitter divorce some years later, but many of the close friends who were interviewed for the original episode had falling outs with the singer).
  • Heartwarming in Hindsight: During "Weird Al" Yankovic's 1999 episode there was a moment where he jokes about his loneliness and that some relatives of his are questioning why he was still single at his age (he turned 40 that year) and due to him being in the music business, that he had to be gay. Less than two years after the episode aired, Al married his wife (and remains so to this day) and became a father.
  • Nightmare Fuel:
    • Occasionally, when the series talks about the death of an artist or band, especially via a plane crash or a murder, there are graphic pictures or a description of the event, such as the Lynyrd Skynyrd crash, the Day the Music Died or Dimebag Darrell's murder.
    • The stalkers episode, which had a darker and creepier tone to it and many of its subjects being interviewed anonymously. Also, it delves into how the law was mostly powerless to do anything for a long while. Thankfully, the episode only aired once.
    • The description of Vanilla Ice's 1994 overdose, which included his friends dumping buckets of cold water on him to make him stay awake and him puking up blood and going into convulsions.
    • Meatloaf discussing his childhood, namely his relationship with his abusive father. He doesn't spend much time on it, but at one point after his mother's funeral while hanging out with a friend in his room, his father became angry at him and tried to stab him with a butcher knife. Had Meat not rolled out of the way, he would have been killed. Also, he thankfully had the foresight to tell his friend to leave before the situation escalated to that point, or else he could have been harmed, too.
  • Spiritual Successor: To a late 1996 VH1 special hosted by Blair Underwood, Dying in Vein: Rock n' Roll on Heroin. One of the segments featured Sublime's Bradley Nowell, at a time when his death was fresh in pop cultural memory and before the network was only beginning to shift towards younger-skewing acts. BTM would be pitched months later using the same format and debut in August '97.

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