Make and distribute free crystal sets to all the settlers in Kansas, Nebraska, the Dakotas, and wherever else circa 1880. Build a huge nuclear-powered transmitter on a cheap mountaintop to maximize coverage. Blast classic rock from the 1960s-1990s 24/7/365 for years.
Translate a few of the nuttier Chick Tracts into whatever language Paul the Apostle read and give them to him. Similarly translate Jesus Christ, Superstar or Godspell (whichever’s weirder) and show it to him. Lead him to believe that this is what Christianity is in the future.
(Or, even better, kidnap Paul the Apostle right before his conversion experience and drop him off outside a gay bar. He should fit right in.)
Hire someone to fly a plane and drop leaflets saying “LEE HARVEY LOVES JACK” on Dallas on November 21, 1963.
Mail a copy of “Loose Change” and some other 9/11 Truther nonsense to the NSA and Osama bin Laden in September of 2000.
Phone a tip to Woodward and Bernstein claiming G. Gordon Liddy is an operative of the Committee to Re-elect Checkers.
Mail Fermat Wiles’ proof of his Last Theorem, suitably translated.
All those famous photos? The sailor kissing the nurse on VJ day? Nguyen Ngoc Loan shooting the VC sapper? The Yalta Conference? The guy stopping the tank in Tiananmen Square? In every iconic photo, I’d be there waving my privates at the camera.
I’d go to Stonehenge, and topple most of the stones from their perfectly-aligned positions. Then I’d go to Pisa, Italy, and plant a small bomb under the Tower . . . just enough to tilt it a few degrees. Then I’d visit the Academy of Fine Arts in Vienna, in 1907, and see to it that Hitler’s acceptance letter never gets delivered.
I’d identify all the greatest scientific, moral, artistic, and political leaders in the last two thousand years and dust their underwear liberally with itching powder. Daily. Fuck you, progress!
Careful everyone, John DiFool is clearly the owner of a time machine and is looking for ways to be a dick
However I will be glad to give you my trademarked list of ways to screw with the world if you’ll just deliver next weeks winning lotto numbers to me today. Once the prize money is in hand you will have the knowledge to be the dick you’ve always wanted to be.
I would go back in time 40 or 50 years and plant a huge number trees across many acres, and tend them periodically so when they grow up they spell out ‘Microsoft Outlook sucks!’ from above.
I would go back and murder the parents of all the members of Journey.
Just so I’d never have to hear “Don’t Stop Believing” EVER AGAIN!
Of course there is nothing dickish about that.