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Tear Jerker / Epic Rap Battles of History

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  • The line during the 'Bill Gates Vs Steve Jobs' rap when Bill says,"The whole world loved you, but you were my friend!" right after Steve Jobs dies. They may have been business rivals, but they were also friends, so it's a little upsetting to hear.
  • Billy Mays' death, right after delivering his famous 'But Wait, There's More!' line. He clutches his chest, obviously in pain, then slowly falls out of frame, with the next shot revealing his tombstone.
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  • In Barack Obama vs. Mitt Romney, during Abe's verse, no matter how much you have laughed up till that point, it's always heartbreaking to hear how Abe died in real life, especially in Abe's line "I FOUGHT FOR WHAT WAS ON MY BRAIN UNTIL A BULLET WENT TROUGH IT!!"
  • Romeo and Juliet vs. Bonnie and Clyde. Even the announcer didn't see it coming.
    • Just the death of Romeo and Juliet was enough to throw Bonnie and Clyde for a loop.
  • Vladimir Lenin rapping about how Stalin tore down everything he was trying to build.
    Lenin:[jumps down into the rap battle with great fury] I have no pride for you who ruined everything my revolution was doing to stop the bourgeoisie!... Our whole future was bright/You let your heart grow dark/And stopped the greatest revolution since the birth of Marx!
  • Poor Stedman. Just...look at him...he's so sad...And it's even sadder when he and Oprah have been in a very on-again, off-again relationship.
    Oprah: Once you go Oprah...
    Stedman: [pained look on his face] You can't go baa-aack...
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  • Subtle, and a bit undermined by Steven Spielberg Mooning Hitchcock immediately later, but Spielberg's second-to-last line implies that one reason why he's so angry at Hitchcock is because the latter refused to see him when he came to visit his idol and inspiration.
  • Stan Lee realizes he gave a diss a bit too far, and confesses how much he misses and respects Jim Henson. Henson simply comforts Lee in response.
    Stan Lee: But the truth is I-I miss ya, you were gone too soon. You were like watching a beautiful sunset... at noon.
  • Frank Sinatra mocks Freddy for dying of AIDs. Freddy's delivery shows that by his death the disease got the attention it needed for people to work towards a cure.
    Frank Sinatra: You played butthole roulette, and you lost the draw!
    Freddy Mercury: I took one for both teams from a disease no one knew existed. I didn't leave a mark on history; I French-kissed it!
    • Not just that, but Freddie's opening line, and sadness in his voice, really drives home that not only was he the subject of homophobia and bigotry throughout his career, but that he's used to the hate he's gotten for his fame.
  • It also goes towards Nightmare Fuel, but Jack the Ripper's lines about leaving families heartbroken by his murders, and how he got away with it all are a very firm reminder of what happened in Victorian London. It's as horrifying as it is saddening.
  • Pompey the Great being ruthlessly garroted by Catherine the Great after only getting half a line. What really drives it home is how excited he looks at having a chance to battle before being killed.
  • While his appearance is awesome, Lincoln's utter shame at how far the Republican Party has fallen is pretty sad. Unlike last time where he dissed both equally, this time he focuses all his fury on Trump who he hits twice. The guy is clearly disappointed with how his party could seriously consider electing someone like Trump.
  • Peter and Lloyd's second battle sees the two launching such vicious attacks on each other that several fans were seriously worried they were watching the final episode.
    • The show took an almost two-year-long hiatus after this battle, stoking those worries. True, the fact that they came back for Season 6 means they resolved their disputes, but at the time it was deeply unnerving.
    • As well, buried in the lyrics is the fact that Lloyd mentions he's on edge because he had a fight with his wife the night before.
  • "George Carlin vs. Richard Pryor" is quite bittersweet throughout, as we get five legendary comedians of whom the only one still alive at the time is convicted rapist Bill Cosby. In particular, Robin Williams' appearance was the most heartbreaking because of the circumstances of his death.
    • While the other rappers did make light-hearted references to their low points (Pryor makes jokes about setting himself on fire, and Joan to her numerous plastic surgeries), Robin's are much more raw and direct. He looks directly into the camera while saying that stand-up comedy is a hard line of work and that he and the other rappers present have all used drugs at various points (while gritting his teeth as if needing a fix). His final line is even stating that he plans to "set himself free," referencing the suicide his depression eventually drove him to.

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