I am not sure if this is the oldest case but Herostratus certainly fits the description of an ancient troll. In Ephesus (modern day western Turkey near the coast) there was a notable temple of Artemis, it was described as one of the seven wonders of the ancient world; and roughly 300 years before the birth of Christ, Herostratus burnt down the temple. When the search for the perpetrator began, he took responsibility, claiming to have done it to become eternally famous. The people of Ephesus condemned him to death, and more, they made sure that his goal would fail, that he would be forgotten by history and left to the void. They banned the mentioning or writing of his name and of his crime. The fact that 2300 years later I am able to mention his name as one of the oldest and possibly most daring trolls, is suitable indication that somehow the edict banning the mention of his name was not particularly successful, and Herostratus will most likely be infamous throughout the rest of history.

For modern instances, Abbie Hoffman's Youth International Party (Yippies) is a pretty good example in the 1960s.

Their activities include:

1. Going to the New York Stock Exchange above the trading floor and dropping real and fake US dollars onto the floor and watch people scrambling to pick it up.

2. Holding their own "parallel convention" in Chicago 1968 during the Democratic National Convention, nominating a literal pig they bought from a farmer as their presidential candidate (the pig was subsequently arrested)

3. When Hoffman and another leaders were subpoenaed by the House committee on UnAmerican activities, they went dressed as a revolutionary era American soldier and a Vietcong respectively, handing out copies of declaration of independence to the people attending.

4. Organizing "smoke-ins" at places where patriotic movements/gathering were taking place, blocking traffic etc and smoking cannabis at those locations.