Annie Gunn's is one of our favorite places to go and spend an evening. We go 3-4 times a year. It is expensive and you should make an event of it. You should do the WHOLE meal, cocktails, cheese or chacuterie board, wine, meal and dessert.
Annie Gunn's is known for their wine. They have an EXTENSIVE wine list. It is 39 pages long! So, I begin looking at it and researching over a week before we go for dinner. They also employ a full time sommelier. John Cain, whom we've met before, was on duty last Saturday night. We ordered our wine from him. We chose a California Cabernet called Buck Shack. We chose one that had been aged in a Bourbon Barrel. It was noted to be interesting. It was good, but I don't know that I found the Bourbon Barrel to change the flavor much. It still just tasted like a nice California Cab to me.
We ordered the cheese board and enjoyed it as always. Annie Gunn's is part restaurant and part store. The Market next door is filled with wonderful things to eat (meats, cheeses, wines, crackers, breads, spread, etc.). So, the chef makes the cheese board from an array (usually 4, from hard to soft) of cheeses from the Market. Then the rest of the board is filled with fun items like fruits, nuts, jam, olives, a little piece of a fig bread, and crostini. This all comes with a basket of warm rolls. It is the best $20 you can spend because it is different each time and it is fun. You nibble on a variety of things with your first glass of wine and you enjoy each other.
The food at Annie Gunn's is rather eclectic. They have a true chef, but they also have a lot of unstuffy food. You can just get a nice French dip sandwich or a burger with fries. But there is also a wide variety of expensive steaks, chops, and fish.
I decided to make an appetizer my meal. The waitress talked me into making it an entree portion and I should have just stuck to my guns and said I only wanted the appetizer. I ordered the lump crab and andouille sausage cake with chipotle chile aioli. The appetizer was 2 cakes with some black bean salad...for $15. The waitress told me I could get 4 cakes with some whipped potatoes and a vegetable for the entree. Well, I wanted to try the black bean salad, so I got that and the potatoes. The potatoes were fine (whipped garlic mashed potatoes...nothing bad...fine). I was kind of disappointed in the black bean salad. It was tiny black beans (that I found slightly undercooked...which I guess is better than over cooked). They were room temperature mixed with some finely diced onions and maybe a little jalepeno. They really didn't have much flavor and I found them to be a little dry (which is weird because they were in a bit of juice...but think underdone beans...dry). The reason I was bummer later was because I couldn't eat all my meal and I had paid $38 instead of $15 to add 2 more crab cakes (that I was taking home) and some potatoes! That was a dumb move on my part. I really did like the crab cakes. The crab was big and the aioli didn't overpower the taste. I don't know that I really tasted the sausage at all...I know andouille adds spice, but that's what the aioli was doing, so the sausage was not necessary.
Mike had steak frites. His steak was very nicely prepared and it had a really nice caramelized onion sauce on the top. I know it was good because he dunked his fries in it.
For dessert we had some warm apple "pie" with vanilla bean ice cream. Mike always gets cappuccino with dessert. It was a nice size to share and it was perfect to top off our meal.
Annie Gunn's is difficult to get in to. We usually pick a date about 3 months in advance and make a reservation...just for the heck of it. It is a nice thing to do once an awhile.
Crab cakes, garlic mashed potatoes and black bean salad. (Obviously I've eaten half of this already...sorry). 
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