I want to be your friend if you win the lottery! I would even help with the clean up.
A first class airline ticket to Australia.
When we still sailed, we used to dream of having a custom-built sailboat, so that would probably top the list. Altho that would only be a stupid purchase if we intended to maintain it ourselves. However, having won Powerball, we could afford a crew to do the dirty work, and we could just enjoy the fun parts of having a boat.
If, however, by stupid, you mean something impractical, bordering on insane, I’m thinking something like buying all the seats for a particular performance, and sitting alone to watch it. 
I don’t have huge dreams when it comes to lottery winning daydreams. Just that my new house would have a whole house generator, a heated driveway, and a small but real movie theater in the basement.
Buy a large house on the big island of Hawaii.
I can not think of anything impractical, or even stupid, guess i am just kind of boring.
Selfish perhaps i can touch.
220 acres (already know what tract near me i would buy)
Build a large but not fancy house. I prefer large sturdy oldschool that lasts 200 years, a decent chicken house for my chickens and ducks with washable concrete floor and bigger pasture, a stupidly large garage, 3 bays for service, 8 for parking.
(Damned right i am fixing my own stuff, not trusting some shop to properly service 40+ year old vehicles, they dont even know what points are now days) and a barn for the tractor and implements.
Then i’ll install a full DS3 line for internet.
He’s in! He’s out! He’s in! Done!!
How about a large solar array / battery bay / generator?
That way you can run super green but be fully covered for when the sun dont shine?
Well unless you are too far north for solar?
I’d also buy a bejeweled crown to wear in public, along with a scepter. I’ve always wanted a scepter.
Commission my favorite bands and groups to create albums together.
Another 10 years of Futurama and 6 more years of the Cleveland show
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First off, I would hire the biggest, most luxurious sailboat I could find, along with a cracker jack crew and staff, and take a year to sail around the world, stopping into any port of call that interested me. I would also buy a fully restored 1969 GTO in that pretty dark green color that Pontiac had available as a stock color during that period. I would pay to have said car shipped to each of my ports of call so that I would be able to visit areas around my ports in a truly worthy vehicle.
Upon my return, I would buy a little place up in the mountains away from it all and possibly that island Johnny Depp owns in the Caribbean if his money troubles force him to sell it.
I’ll take 1666 acres on the Animas River with 666 acreas planted in cider apples and 333 planted in 51% corn, 20% 6 row barely and 29% rye and the other 666 used to rotate with the grain probably beans and sheep. Then I want a 20,000 sqft home with a 5,000 sqft distillery built below the basement (house built on bluff overlooking river so I’ve got 100’ of down available to me) with 25,000 sqft barrel cave.
That should be right at 100 mil to build and buy the land then ill need funding for the first 10 years so another 50 million. On the plus side it should make $120 million per year starting in year 9 so once were through start up it would be self sustaining.
A big sod farm. Have somebody else run it, and build a nice compound in the center. Use the farm for my fleet of ultralight aircraft.
A beach house.
I’d also find Elizabeth A. Lynn and offer her vast sums of money if she could write a few more Tornor books.
I would buy up a majority of the lots in a new HOA-ruled addition. I would then use my owner votes to abolish the HOA. I would then park double-wides on all my lots and give them away to whomever I should choose.
I always thought I’d buy a gigantic Kenworth tractor truck with a ton of lights and chrome. Just to drive around.
I would buy a cabin on one of the around the world cruise ships. A solo ship would get boring. Lots of stimulating people on those cruises.
Travel First Class air or fractional private jet travel when not cruising.
A modest contemporary home in each of these areas: US - San Diego, Washington state, Colorado. Europe - Italy, Tuscany; Spain - gold coast; France - Cannes; Scotland - St. Andrews, Amsterdam, Copenhagen. . Australia - Sydney, Brazil - Belem. I’d rent/trade them when not living on land.
Learn the piano.
That is definitely on my list. Queen Mary II New York to New York, Queen’s Grill Grand Duplex suite.
I would hire Peter Jackson and production crew to make a multi part movie of the Silmarillion
I would refurbish the Hubble and make it available to High School students
I would invest millions in Microphage research as frontline anti biotic treatments
I would build a fleet of hospital ships that will sail the world providing medical services which may be difficult or outlawed in anti choice countries
guess I need a few more power balls