Tear Jerker / Beverly Hills, 90210

• Brenda learning that Dylan cheated with Kelly (Season 3's "Back in the High Life Again"). Even though Brenda knew Dylan had an affair with someone during the summer, she didn't know who with. When Kelly revealed that she was the one, it was the ultimate betrayal. Brenda losing her boyfriend to a person whom she thought she could trust, which could easily connect with viewers who had a similar experience, and also goes to show that betrayal is never at the hands of your enemies. It doesn't help that Dylan acts very blase about it, though Kelly tries to soften the blow, though Shannen Doherty's performance speaks volumes.
  Kelly: Neither of us wanted to hurt you.
  Brenda: You didn't care how I felt at all, Kelly!
  [...]
  Brenda: Look, I hate you both. Never talk to me again!
  • After the death of Dylan's father, Brenda puts aside her anger to invite Dylan to stay with the family so that he won't be alone.
  Brenda: Years from now, your dad will still be gone and I'll just be some girl you knew in high school.
  Dylan: [Tearfully] No, you won't, Brenda. Not after everything. [They hug, and Dylan's remorse for hurting her and relief that she's beginning to forgive him is palpable]
• Everything about Dylan's relationship with his parents. To put it that he has Daddy and Mommy issues throughout the show, is mildly.
  • His father provides for him materially, but never is there for him and even is alluded to abuse him physically due to his alcoholism. Then when Dylan and his father finally bond, Dad is murdered.
    • Dylan's screams of agony at watching his father's car blow up are this and Nightmare Fuel.
  • Then turns out Dylan has a half-sister Dad didn't tell him about. Then, right when Dylan's over Dad's death, Dad turns out to have faked his death and to be living happily with a new wife and child. And then after seeing each other one time, Dad and Dylan vow to never see each other again due to safety reasons.
    • And looking for his father's murderers is what gets Dylan's newlywed wife killed, just when he has found a loving relationship—Dylan's screams over her dead body echo that over his father's death.
    • Also, Dylan has inherited his Dad's worst qualities, like his alcoholism, tendency towards violence, and tendency to abuse / turn away from the people he loves. He's actually repeating the cycle.
  • His mother abandoned him, and when she shows up in his life, she's only being nosy and annoying and doesn't do anything to help.
  • And that cute little half-sister? She winds up as a 14-year old drug-addicted prostitute living on the street...
  • Jim Walsh, after initially hating Dylan, acts as a parental substitute towards Dylan for a while... until Dylan and Brenda break up, Dylan's father dies, and Jim and Dylan are outwardly hostile towards each other again.
• David's breakdown at the end of The First 50 Years, while on-air with his radio show, revealing his guilt over his neglect of his childhood friend, and his frustration with everyone who offers him sympathy, when none of them could have picked Scott out of a lineup. Doubles as a moment of Awesome for Brian Austin Green, who honestly turns in his best performance in the entire series.
  David: Everyone's coming up to me, wanting to be my new best friend! But what about my old best friend?
• The death of Luke Perry on March 4th, 2019.

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