What would you do if you won the lottery? I think I would hire a lawyer and an attorney. I’d invest the majority of it and live off the interest.
The being instantly “famous” part would be the hard part for me. I think I would have to temporarily move to a nice apartment in a major city so it would be eaiser to blend in. Then I would probably start building a house in a nice gated community, or at least somewhere where I can secure the hell out of the house.
I would pay all my bills and become debt free!!!
I would buy a mini cooper and a mercedes.
I would build a house.
I would help my mother with her house remodeling woes.
That’s about it. . .
Move the money off shore into a tax free jurisdiction. Create a foreign corporation. Buy property/assets under corp to take advantage of favoured corporate taxation policies.
Share my windfall with family and friends ones.
Depending on exactly how much I received, I’d start my own brewery/pub and live out the rest of my days bartending in my own pub.
Would these be two different people?
I’d make sure the folks were set up in a nice assisted living place with plenty of amenities.
I’d get a newer car with better mileage and not so many quirks.
I’d sock money away for retirement.
My error: Lawyer and Accountant
In order:
-Settle all debts
-Buy a new, economy car
-Buy a house
-Invest about $1M (More or less depending on how big the lottery winnings were)
-Complete my education
sit around all day and do nothing.
Yeah, one to keep an eye on the other.
I think I’d singlehandedly fund Indiana Public Radio, so I’d never have to hear another pledge week. Then I’d make 'em drop The Whistle and Padlock.
I’ve often thought it’s too bad somebody didn’t put Leadbelly and Muddy Waters on a retainer in the early years and give them a fair contract. If I could find a similar genius today, maybe I’d bankroll him or her. 
Pay off all debts.
Buy land and have house built (and hire housekeeper to help with upkeep!).
Pay off family’s debts, buy my parents a house, and bankroll Dad’s retirement.
Have weight-loss surgery, and follow-up cosmetic procedures.
After all surgeries–NEW WARDROBE!!
Take family to Disney World and other theme parks.
Set up my own recording studio.
Take some college classes–just for fun!
We’d pay our bills, give our family members a share, buy a nice boat, and set up a scholarship fund for kids to study science and engineering.
And if it was a big enough jackpot, no I wouldn’t keep working. At least not where I am. I’d find something else to occupy my time and my mind.
I would pay off my little house and fix it up the way I want to. I would put enough money away for my kids to go to college (if that’s what they choose to do) or get a good start in life, I would put enough away for my husband and I to retire on, and I would give a chunk to the Make a Wish Foundation…anonomously. I wouldn’t want press. Then, I’d take my family traveling.
-See how much Revenge I could afford.
-Buy all the “little things” that really aren’t that expensive, but were/are just a bit too much for me to afford.
-Sit in the dark, in the middle of the day, listening to recordings of Beethoven and the Red Army Chorus, at perhaps painfully high volume.
-Do what I’m doing now, but without so much angst.
Assuming we’re talking a decent sum here, say $10 million or so…
I doubt I’d get bored that way before I’m 125.
Buy several houses in Montana - downtown Missoula, the Flathead and something on the Ruby or the Big Hole rivers.
Hire several of my best friends to be sports buddies. They wouldn’t have to do it all the time and I wouldn’t make them rich, just very comfortable. In return, I get 3-5 weeks of their time every year to go fish, hunt or drink all over the world. Since I would be their boss and pay them well, the wives couldn’t complain. And it’s what we would do anyway if we had more time and money.
Spend 10-20 hours a week doing volunteer work. Be an aide at a daycare, serve on a board for a non-profit, whatever.
Buy a couple of houses in the Caribean on small, rural islands.
Set my mom up for anything she wanted.
Spend most of my time doing sports - fishing, hiking, backpacking, snowboarding, skiing, snowshoeing, mountain biking, kayaking, river rafting, golfing and all the other things I don’t get to do enough because of the need to work 40 hours a week.
Get me a really fine trophy wife. 
Who knows how to row a boat and load a pack and is better at fishing than I am.
Whistlepig
Provided the winnings were enough, I’d be a kayak bum for as long as the bod holds up. Hire an attractive young lady to shuttle me and my fellow kayak bums from river to river and to watch my dog.
And feed the naked, clothe the hungry, all that.
Ski at Lake Louise and Blackomb for the winter, paddle in the Lochsa area and points south in the early spring, paddle the north shore of Superior in the summer, and travel the continent in the fall doing the gallery/museum thing. Repeat and rinse, with changes of venue. Lots of photography and writing in the down time.
If my uncle is any example, I would squander every penny, lose my wife and house, gain 100 lbs. and live off welfare starting at age 60.
Winning the lottery is one of the most dangerous things that someone can go through. Many don’t make it out very well.
Seriously? I’d wonder what the hell was going on, because I never buy lottery tickets. 
But assuming it was legit, I’d catch the next flight to NYC so I could huddle with my uncle and figure out a plan. Like the OP says, I’d like to be able to invest whatever it would take to let me live off the interest.
In terms of pure fun? I’d:[ul][li]pay off my debts[/li][li]buy a new car (something sporty but not obnoxious) and something used that I could take to the track[/li][li]learn how to fly helicopters and small planes, which would help me to[/li][li]never fly coach again[/li][li]buy my mom the one-story house she needs, with a proper housekeeper[/li][li]spread some untaxable cash around to my cousins and their kids[/li][li]give my best friend a chunk of money to go toward his son’s education[/li][li]set up some kind of charitable organization and then hire people to run it[/li][li]figure out where I want to live and make it happen, while renting whatever my heart desires in the meantime[/li][li]hire a personal chef and a personal trainer[/li][li]travel, travel, travel[/ul][/li]I don’t think I’d quit my job: I like what I do, and I’m only 34. I’d take a leave of absence to travel and party and finish my master’s degree and stuff, but I think I’d want to work for a while longer. I might eventually go part-time, though, so that I could spend more time finding/being in a band and doing volunteer work. I think it would be kind of fun to work full-time but never worry about being able to afford to do anything. Happy hour? On me. Poker game? I’ll buy 3 sets of chips. Conference in Seattle? I’ll pay for myself.
Not that I’ve spent a lot of time thinking about this or anything.