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The latest episode in HBO’s unflinching family drama Succession (Sundays at 9pmEt only on Crave) produced one of the show’s most cringe-worthy moments and across nearly 20 episodes, there have been many.

Kendall, the character we love to hate and hate to love played to perfection by Jeremy Strong, has been gunning to follow in the very very successful footsteps of his father Logan (Brian Cox), the founder of media conglomerate Waystar Royco and patriarch of the Roy family. Despite winning the genetic lottery, throughout two seasons we’ve watched Kendall fail countless times trying to prove his worth to (read: suck up to) his father and win the succession (ha).

Last night, he may have finally crossed the line in his efforts to ingratiate himself to his hard-to-please daddy. And we’ve never seen such evident parental disappointment.

During the party celebrating his dad’s 50 years in business, Kendall followed up his brief remarks about his father by ripping open his jacket to reveal a Logan Roy baseball jersey. And that’s the moment the squirming began.

Kendall then plunged headlong into an off-key rap about how great his dad is—featuring such fantastic lines as “50 years strong now he’s rollin’ in a sick ride,” and a constant refrain of “L to the O.G. Dude be the O-G-A-N.”

We were just watching from our couch, but our faces were an exact reflection of those in the audience. A combination of shock, confusion, and complete mortification. But for some reason, we just can’t seem to look away.

“Bro, don’t get it twisted,” he continued (it’s a long rap). “I’ve been through hell. But since I stan Dad, I’m alive and well.”

He may be alive and well, but we are DYING. Is it just us or are we getting flashbacks to our third-grade talent show? *shivers*.

After what seemed like a lifetime, Kendall finally finished his pathetic daddy rap by placing a tartan baseball cap on his stone-faced father’s head. And honestly, we pretty much just blacked out after that.

It’s deeply sad how far this man has gone just to get Logan’s (AKA, L to the O.G.’s), approval. Kendall’s whole pathetic/estranged/sociopathic thing he’s got going on is clearly a product of being severely damaged by his toxic money-grubbing family. In reality, we think he just needs someone to love.

But to love this guy, he needs to first stop making us feel like we want to go dig ourselves into a hole and hide for the remainder of the season.

Catch new episodes of Succession on Crave, Sundays at 9pmET.