A phrase I’ve found frequently misused is “it’s not even funny”.
Sample correct usage: “They were losing so terribly, it’s not even funny”. In this case, imagine a world-beating super awesome team playing against a lame one and quite predictably beating them. To a point watching this game is kinda funny as the awesome team easily outclasses the other, probably mocking and teasing them during play. But imagine if the super awesome team gets all brutal, mercilessly thrashing the other like a lion crushing a helpless puppy, the weaker team’s players lose all hope, playing with defeated spirits, trudging along with hopelessness and despair. Now that isn’t funny, not one bit. It’s probably sad and downright painful to watch. As I see it, the phrase is appropriate when something in mild amounts is humourous or amusing but becomes painful to experience at larger magnitudes. Like “I’m so broke it’s not even funny”.
When did being broke become funny? Why would your shitty financial acuity amuse anyone, especially you?! Poverty in all shapes and sizes isn’t funny. I would’ve written a longer post but I have so many things do it’s not even funny ;)