For the most part, I've had generically good holidays with family. Very few stand out one way or another, buuuuuut...
Several years ago my husband's uncle had a stroke and was ordered onto a low-sodium diet afterwards. That aunt and uncle hosted Easter a few months later and refused all offers to bring something along (despite that being the family norm). They'd made every single dish with salt substitute. Every. Last. One. Every part of the meal tasted like metal. When one person asked for some actual salt to put on their food, the family started lecturing about how terrible salt is and how they were never going to have it in their house again. Very little of the food was eaten. I'm not sure what the rest of my in-laws did, but my husband and I had to get McDonald's on the way home.
On the good side, last Thanksgiving my husband was on call and all our local friends were out of town for family dinners, but some of our non-local friends had just found out that they couldn't get affordable tickets to their family Thanksgiving across the country, so they flew in to see us instead! I made my first fully solo Thanksgiving dinner with all the trimmings (and got my head swelled by all the praise!), and we spent the whole long weekend playing Pandemic Legacy Season Two. It was AMAZING. We ate off the leftovers whenever we got hungry, drank loads of coffee and Surge, and just had a great time.
What are your best and worst holidays?