10. Roman’s breakdown at the funeral – “Church and State” (Season 4, Episode 9)
Despite his recent involvement in helping a fascist win the presidential election, Roman surprisingly emerges as the most sympathetic character at his father’s funeral, a testament to the show’s remarkable writing and acting. While Roman has shown moments of vulnerability before, it is during this scene, when he abandons all pretences of “pre-grieving,” that his true pain unfolds.
Struggling to hold himself together, Roman barely manages to utter the first line of his eulogy before completely breaking down at the sight of his father’s coffin. Desperate for comfort, he clings to his siblings as they gather around him. Kieran Culkin delivers one of the most devastating lines in television history, asking “Is he in there? Can we get him out?” Roman, shedding his snarky persona that typically masks his emotions, reveals an incredibly authentic vulnerability. However, this raw display of emotion effectively seals his fate, blocking him from ever attaining the CEO position.