You are given $1,000, which must be spent on entertaining a celebrity of your choice. Which local restaurant (within one hundred miles) do you take him or her for dinner? (Or you can cook an expensive meal at home for him/her, too.)
I would take the celebrity to Fogo de Chao in downtown Austin, Texas, a Brazilian steakhouse where cuts of meat (picanha, filet mignon, etc.) are brought right to your table and sliced right there off of a giant skewer, and we would order a variety of things, especially the mango Chilean sea bass - and wines as well - and then dessert would have to include the papaya cream and caramelized pineapple.
There’s a little place in Leonardtown called The Front Porch. It was built in the mid-19th century and stayed in the same family till about 11 years ago. Whoever turned it into a restaurant did a wonderful job, both with the decor and with the menu. We’ve always had a wonderful experience when dining there.
I’m not sure I could spend $1000 there unless I took a whole group of folks, so but if it was just 2 of us, the server would get a helluva tip! 
I can’t imagine why I’d need to spend $1000 at a restaurant or cooking at home. With the possible exception of incredibly expensive wine then not much more than $100 a head is the most I can imagine spending without totally wasting the money. There isn’t much worth that much around here worth the high prices, maybe the Nordic Lodge for a $95 a person seafood buffet if they’re a big eater and seafood lover. Otherwise a couple of mid to high end steak houses at a casino or someplace in Boston. Be a lot easier and a better time to just cook up a storm here at home based on what kind of food they like.
Does French Laundry count as local to San Francisco? Because if so, I’ll need to decide whether to get the foie gras supplement AND the wagyu supplement or just the truffle supplement to stay under the budget.
Two choices.
One is that I’d have my boss, who’s a fantastic caterer, do a meal for two. Caviar, shrimp, chanpagne, and so on.
The other is we’d go to a local diner I love. Best breakfast in town. Or, if it was dinner, they have super burgers, American comfort foods, and small steaks… I know, I know, the latter doesn’t sound fancy. But it’s splendid, and truly local, food. I don’t know enough about the other restaurants around to compare.
Most likely Jack’s Oyster House in Albany. $1K would be hard to make, but the food is great and the place oozes tradition and class.
Alinea in Chicago. $1000 should be enough unless we go crazy with drinks. I haven’t been yet, but my brother and his wife have been there three times, averaging $700 for two with wine and tip.
Well, I’ve got all of Brooklyn and Manhattan within 100 miles of me, but any celebrity I’d be willing to treat would probably be happiest with a tuna melt at Eisenberg’s Sandwich Shop.
Too bad Lundy’s closed.
Lundy’s was the best and you didn’t have to spend a thousand bucks for a fantastic meal. Also the best and no longer around to impress a celebrity with: Gage & Tollner.
As a chain with 29 locations, Fogo de Chao isn’t what I think of as a local restaurant - in Austin, I’d take them to Uchi.
Well, sure, but if someone is giving me $1000, I might as well take the celebrity to an expensive-ass place I haven’t been to before. (I’m assuming you’re not allowed to keep what’s left over. Otherwise, I’ll take him to Johnnie’s Italian Beef and pocket the $980 in change.) I can afford the sandwich shop. 
My immediate go-to is The Pearl Cafe, in Missoula, which is the main high-end French restaurant around here. It’s extremely nice, but it isn’t $1,000 nice, because the local economy couldn’t support that, much like how the local culture won’t support a restaurant with an actual dress code. So it would be hard for two people to spend $1,000 total at The Pearl, unless they were complete souses and kept themselves marinated in high-end wines.
But that’s the obvious place, and it isn’t anything special on a global scale. You can get good French food literally anywhere on Earth which can support nice restaurants. Personally, I prefer more local food, such as Red Bird, in Missoula, which is more eclectic and more likely to have a unique menu, or the Double Front, in Missoula, which makes some of the best fried chicken in the state, if not the region, or Nap’s Grill, in Hamilton, which has the best burgers in the region, easily. Spending $1,000 at any of those places would be self-defeating, but it would be equally self-defeating at The Pearl, so the only reasonable course is to treat that as part of a total entertainment budget and go do something else with it, too.
GOD, how I miss Gage & Tollner.
I dined there at least two dozen times between 1984 (when I moved to Park Slope) and 2004 (when it closed). When my authors came in from out of town I would drag them out to downtown Brooklyn to charm the living shit out of them with G&T. And Edna Lewis’s cooking was magnificent.
What Antoine’s is to New Orleans, Gage & Tollner was to New York.
Hey! Nobody said I didn’t get to keep the change!
(If I can’t, I would leave the counterman at Eisenberg’s a $980 tip)
I’m sure Kesha would love Lao Sze Chuan in Chinatown for some Sichuan hot pot. Then there would be $900 or $950 left over!
Coney Island for Texas wieners. So cheap that I don’t have to narrow my guest to just one celebrity.
In Houston, that I’ve read about? Oxheart.
That I’ve actually eaten at? Hugo’s. Don’t worry: we’ll kill the rest of the 1000 bucks on booze. I’m kinda’ curious what Bridget Burke will pick, when she shows up.
For Austin, I love Fogo (and they have the best salad bar you’ve ever seen, believe it or not) but I’d actually take the celeb to Franklin BBQ. (And spend the rest of the money figuring out whether Côte-Rôtie, Late-Picked Zin, or Amarone was a better match for the food. With smoke-bomb Scotches for lagniappe.)
Uchi’s supposed to be great, but Franklin is the finest Texan-pit BBQ on the planet.
EDIT: Oh, and I’ve not dined at the French Laundry, or any of his cafes, but it would be hard to beat, for me, the experience I had 20 years ago at Masa’s in San Francisco. And it’s closed, I see. Of course it is. Sigh. I wonder how Julian Serrano’s later restaurants compare?
Franklin would certainly be a great choice if you want to spend a solid 3-4 hours with the celebrity (waiting in line with tourists ;))
Why the HELL would I treat a celeb who is a million times richer than me?
I wouldn’t have the foggiest idea where to go for dinner in San Francisco and I can’t cook, so how about KFC or Pizza Hut? 
If we’re looking for a local (Sacramento) restaurant, I’d definitely choose Biba. It’s our go-to choice for celebratory dinners; we’ve never spent anything remotely close to a thousand dollars on dinner there, but I’m sure I can find something on the wine list to pick up the slack.
But going by the OP’s definition of ‘local’ being “within 100 miles”…Yountville is only 70 miles from home, so I don’t think I could pass up the opportunity to have a ‘free’ meal at The French Laundry.