Watching Will and Diane’s relationship crash and burn. You just have to cringe.
For that matter, watching the relationships between Alicia and Will, Cary and Diane, Cary/Alicia and the firm, and just about every other relationship on the show just explode one after another in the beginning of season five.
Diane breaking into tears when she realises her dream of becoming a judge probably just got squashed.
Will as he makes the decision tree in ‘The Decision Tree’. The look on his face as he makes his set of questions for Alicia, and the resulting fantasy/flashback, is heartbreaking.
In a Ripped from the Headlines bit, Elsbeth is called several nasty slurs by a street performer she was enjoying. It’s strangely jarring and upsetting to see our beloved Cloud Cuckoolander be so completely stunned and hurt.
Elsbeth: (Almost in tears) I am not a dirty, stinking Jew!
Everything about the last act of ‘Dramatics, Your Honor’:
When Diane hears the gunshots, her first reaction is fearful concern to find Will.
Kalinda seeing the shoe on the ground and putting it together before pushing past security to get to her dying boss and choking out a sob once she does.
The first person Kalinda and Diane think to call about Will’s death? Even after all that’s happened, they know it has to be Alicia.
Kalinda and Diane breaking down over Will’s body.
Eli’s reaction to Kalinda’s call, and his gentle way of pulling Alicia aside and giving her privacy to hear that Will has died.
The reaction of David Lee, who infamously cares for no one and would sell his own grandmother if it got him a profit. Rising silently from his place in the meeting room, walking blank faced to an office, yelling at the staff there to get out and then, only when he was sure he was alone and unobserved, face crumpling and fighting back tears.
Following ‘Dramatics, Your Honor’, the entirety of ‘The Last Call,’ as everyone reacts to Will’s death.
The saddest are probably Diane, Alicia, and Kalinda’s reactions, but David Lee crying is surprisingly poignant and humanizing.
6x02 "Trust Issues" has Diane leaving her office at Lockhart-Gardner for the last time. She looks out the window, waits for five o'clock, takes a long look around, then picks up her photo of her and Hilary Clinton and walks to the elevator. As she gets in with those leaving with her, she lets out a quiet 'goodbye' to the firm that she helped establish and the last physical tie to Will, her best friend.
When Cary, Alicia, Diane, and company take back the LG offices, it is Alicia who ends up in Will's old office. The undercurrent of lingering grief that passes over her face as she walks in is heartbreaking.
6x10 ‘The Trial’ has Cary taking the plea bargain, pleading guilty to the conspiracy charges for two years in prison.
Cary in general in this episode, as he recognizes that he sees no way out of the situation he's in and unable to prevent going back to prison. Matt Czuchy gives an amazing performance almost entirely in his face, without much dialogue at all.
Alicia breaks down in tears after the Democrat Party rigs the voting machines to gain a supermajority in the state Senate (which affected the State Attorney election) and then betrays her when her opponent demands a recount, which forces her to resign, her attempt to return to the firm she helped started fails when a misunderstanding leads the firm to break with her and, the last straw that breaks the camel's back, Kalinda has to run away because she brought proof against Bishop.
Jackie opening up to Howard and tearing up when telling him about how her mother would make her eat a clove of garlic whenever she laughed, just because she hated her laughter. Suddenly, her entire demeanour becomes much more understandable.
Alicia hitting her emotional breaking point in "Judged," ultimately breaking down about everything, her feelings for Will, her dissatisfaction with things her her life since his death... It all comes pouring out of her at once, and it's Lucca who gives her a Cooldown Hug.
The ending of "Unmanned," where Cary says he's quitting LAL, that while he loves being a lawyer, he can't take the maneuvering and scheming that has defined the lives of the name partners at pretty much every incarnation of the firm anymore.
Throughout the series finale, Alicia works out what to do through imaginary discussions with Will, including a frank discussion about their epic, doomed love story that culminates in a very in-character, very gut-wrenching exchange and an emotionally charged hug:
Alicia: I'll love you forever.
Will: I'm okay with that.
Diane's silent walk out of the courtroom after Lucca asks Kurt if he's had an affair.