9 Cringe-Worthy Moments from the World of Entertainment
Explore the most uncomfortably awkward scenes that left viewers squirming in their seats.
Roman's Million-Dollar Offer
In a jaw-dropping display of disconnected wealth, Roman offered a young child a million dollars to hit a home run. The sheer audacity and insensitivity of the act left everyone cringing as it highlighted Roman's complete detachment from reality. To make matters worse, the cheque was torn up in front of the child, compounding the cringe factor.
Roman Offers A Kid A Million Dollars Season 1, Episode 1, “Celebration” in Succession
The moment encapsulated the tension-filled cringe that Succession is known for, leaving audiences both captivated and repulsed by the display of privilege and entitlement.
Kendall Trying To Impress In His Meeting With The Start-Up Season 1, Episode 8, “Prague”
Kendall's Meeting Mishap
Kendall's attempt to impress at a start-up meeting turned into a cringe-inducing display of incompetence and insecurity. His belittling of the entrepreneurs and lack of awareness about the art world left viewers squirming with second-hand embarrassment. Kendall's desperate attempt to emulate Logan's no-nonsense approach ended in a painfully awkward scene that showcased his severe lack of self-awareness.
Matthew Macfadyen as Tom Wambsgans in Succession Season 2, Episode 9, “DC”
The scene highlighted the tension and awkwardness that permeates the world of corporate power struggles, making it a memorable cringe moment in the series.
Succession Season 2, Episode 9, “DC”
Tom's Testimony Fiasco
Tom's repeated email to Greg Hirsch, 'you can't make a Tomlette without breaking some Greggs', revealed a cringe-worthy and out-of-place dialogue in a formal court setting. The absurdity and inappropriateness of the moment left viewers squirming as it clashed with the serious nature of the Senate Committee on Commerce.
Matthew Macfadyen as Tom Wambsgans in Succession Season 2, Episode 9, “DC”
The sheer cringe factor of the scene was amplified by the revelation that the email was sent 67 times in one evening, making it a standout moment in the series.
Nicholas Braun as Greg Hirsch in Succession Season 2, Episode 9, “DC”
Connor's Concession Chaos
Connor's concession speech took a dark turn as he delved into complicated pettiness and betrayal, revealing his deep-seated insecurity and inability to handle failure gracefully. His bizarre warning about the 'ConHeads' left viewers cringing at the spectacle of a man desperately clinging to delusions of grandeur.
Matthew Macfadyen as Tom Wambsgans in Succession Season 2, Episode 9, “DC”
The scene showcased the cringe-inducing nature of the Roy family dynamics and the lengths they would go to maintain their fragile egos, making it a compelling yet uncomfortable watch.
Connor’s Concession Speech Season 4, Episode 8,
Shiv's Premature Claim
Shiv's premature announcement of her place in the corporate hierarchy at the Pierce dinner caught everyone off-guard and highlighted the unstable nature of the Roy family dynamics. The uncomfortable tension and defeat in Shiv's claim left a lasting impression of the Roy children's desperate need for recognition and power.
Pierce and Roy family sitting at a dinner in Succession
The scene was a classic example of cringe-based tension-building, showcasing the deep-seated insecurities and power struggles within the family.
Kendall Roy gives his speech at the shareholder meeting - Succession - Season 4, Episode 6
Kendall's Stakeholder Speech
Kendall's nervous and unprepared presentation of the new Waystar Royco streaming service quickly turned into a cringe-inducing disaster. His use of a video projection of his deceased father added a layer of discomfort and lack of awareness that left viewers squirming in their seats.
Kendall Roy “F**k The Patriarchy” Season 3, Episode 3, “The Disruption”
The scene was a prime example of corporate misjudgment and the pitfalls of unchecked privilege, making it a standout cringe moment in the series.
Kendall Roy rapping in Succession
Kendall's Controversial Assertion
Kendall's provocative assertion of 'f**k the patriarchy' to rile up the press and create controversy was a self-aware yet cringe-worthy moment. It exemplified Kendall's detachment from the average person and highlighted the privilege that fueled his sense of entitlement.
Kieran Culkin as Roman Roy after texting his father Logan Roy in Succession Season 3, Episode 8, “Chiantishire”
The scene showcased the character's ruthless ambition and the discomforting distance between his life and the reality of others, leaving a lasting cringe-inducing impression.
Kieran Culkin as Roman Roy after texting his father Logan Roy in Succession Season 3, Episode 8, “Chiantishire”
Kendall's Awkward Rap
Kendall's attempt to infiltrate pop culture with his rap at Logan's birthday celebration was a cringe-inducing misjudgment that left everyone on edge. Despite his decent rapping skills, the inappropriateness of the moment made it a cringe overload that left viewers squirming with discomfort and second-hand embarrassment.
A phone in Succession Season 3, Episode 8, “Chiantishire”
The scene encapsulated the discomfort of multimillionaires trying to connect with a world they are utterly disconnected from, making it a standout cringe moment in the series.
Kieran Culkin as Roman Roy after texting his father Logan Roy in Succession Season 3, Episode 8, “Chiantishire”
Roman's Text Mishap
Roman's accidental text of a private picture to his own father was a near-top cringe moment in the series. The moment of realization and the uncomfortable aftermath left viewers cringing in discomfort, empathizing with the sheer embarrassment and awkwardness of the situation.
Brian Cox as Logan Roy after texting his father Roman Roy in Succession Season 3, Episode 8, “Chiantishire”
The scene highlighted the toxic and depressing mess of age-inappropriate relationships, adding to the cringe factor that made it a memorable moment in the series.
Jeremy Strong as Kendall Roy in Succession saying I'm the eldest boy
Kendall's Infantile Assertion
Kendall's assertion of 'I'm the eldest boy' in a final power play was a cringe-inducing display of emotional stuntedness and insecurity. His choice of words and the infantilizing term 'boy' showcased just how small and pathetic he appeared in that moment, leaving viewers cringing at the spectacle of a man desperately asserting his natural right to lead.
Sarah Snook as Siobhan "Shiv" Roy in Succession Season 4, Episode 10, “With Open Eyes”
The scene highlighted the deep-seated insecurities and power struggles within the Roy family, making it a compelling yet uncomfortable watch.
Shiv Betrays Kendall - Succession Finale 0-59 screenshot
