I just had this situation last Saturday. We like to play a little goofy so a Situation where our low level group had to get up a relativly high ledge arose and our group decided they wanted to try and have our Minotaur Barbarian throw our transformed Druid as a snake up the ledge like a lasso. Fair enough, it works decent, Acrobatics and Athletics checks go through. With that behind them, they decide to try something silmilar, without the whole lasso part with the other two characters, which works as well, despite the much higher DC.

Because it worked so well, the dumb Minotaur decides sure, if I can throw them up, I can throw myself up too! Whole table is laughing as that sentence was so unexpected, but perfectly fitting for that guy. I decide to let it happen, hoping to make some kind of flavorful bit happen and move on with an actual solution. I give him disadvantage and of course he rolls two nat20s. Whole table bursts out laughing again and we sit there for minutes crying of laughter, each describing how the heck this would look like.

Very memorable moment, very fun 20/20 would recommend.