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  • Harsher in Hindsight: Fans joked that Tawny's nose problems was due to her snorting cocaine. To the point where both Maven and Andrea suggested that she was under the influence. Tawny was then charged with possession of cocaine shortly after.
    • Verne Troyer's infamous drinking scene is incredibly hard to watch now, especially knowing the troubles he had with alcoholism up to his suicide.
    • Vanilla Ice and Ron Jeremy's friendship is this for those who watched "Surreal Life Fame Games..."
  • Hilarious in Hindsight:
    • In the fourth season, when Chyna's then-boyfriend at the time, Sean Waltman, crashed the set and was begging Chyna to leave with him, he got into a war of words with Da Brat, who proceeded to grab a wine bottle in a threatening manner as if she was about to hit him with it. Sean sneeringly replied that she wasn't gonna try anything with it, and ended up leaving shortly after. Considering that Da Brat legitimately got into trouble years later for assaulting someone with a rum bottle, Sean got off incredibly lucky.
      • Speaking of Waltman, even D-list celebrities know "X-Pac Sucks."
    • In Season Six, Steve's last words, "Goodbye Surreal Life," would become this as it turned out to be the final season.

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