Get Drunk wine? 2-buck Chuck wasn't so bad if your expectations match the price tag. One out of every three bottles of that actually turned out to be pretty good, it's just a bit of a treasure hunt to find those. Rough work.
Apothic Red was not bad either. The Barefoot Bubbly line was also decent and cheap.
Dessert wine, hmm. We didn't drink too much of that. But there was a place in the Yorkville Highlands that did a nice one. Maple Creek, I think?
James Cole does a dessert wine every year that varies in grape varietal and location. I think it's a collaboration thing? I'd recommend them but their prices skyrocketed over the last couple years.
Not worth the new pricepoints.
Far Niente has an excellent dessert wine: Dolce. A bit on the pricey side though, but for a special occasion it can be worth it.
Lava Vine had a nice port-style wine which I think they market as a dessert wine. We also had a nice white port (who knew that was a thing?). I'll have to try and remember where that was from. Wellington? Something with a W...