What: The first free elections in Czechoslovakia’s history in 1990, sweeping playwright Václav Havel into the presidency:

Why: Czechoslovakia was a tragic nation whose citizens were never once free to cast a meaningful vote for their leader. At various moments, it showed flashes of what it could become, only to be crushed by one tank column or another. The last repressive years of the Soviet bloc were ones that Václav Havel spent in prison. Havel’s crime was that he was a playwright, and more troublingly, a darn good one. Not surprisingly an absurdist, Havel wrote of characters who got less comprehensible as they got more conformist. (In The Memorandum, he even invented an “official state language” that of course led to the complete collapse of human communication.) His worst offense was writing a dissident charter in support of—get this—a psychedelic rock band named “The Plastic People of the Universe.” That was enough of that, said the Soviet puppet regime. Havel spent the 80s being shuttled in and out of jail. The locks all opened as the Velvet Revolution swept through Czechoslovakia in November 1989, and within a month, the new Federal Assembly appointed Havel to run the country. But that wasn’t good enough. The people had to get their crack at democracy, and on June 8, 1990, the stalwarts of the old regime ran against a united opposition party called Civic Forum, of which Havel was the leader. One landslide later, a playwright had become the first democratically elected president of Czechoslovakia.

Impact: By the end of 1990, every country in Eastern Europe had newly elected governments. (The Romanians had to turn AK-47s on their dictator first, but hey, these things happen.) Havel became the shining light in the region, at least from the outside. He led the dissolution of the Warsaw Pact, believing that a pact is what countries agree to when they have a choice. He threw open the doors of the prisons, believing that a criminal justice system without justice couldn’t fairly identify criminals. And then when Slovakia declared its independence, Havel did something people just didn’t do in that part of the world: He stepped down. He later was elected the first president of the newly formed Czech Republic, and was re-elected in 1998. He has continued to write plays, pal around with rock stars, and stand as a force for change.

Personal Connection: I’ve told this story so often that I can’t imagine anyone’s reading it for the first time, but here goes: My girlfriend Lisa and I visited Prague on May 6, 1990, just a month before the election. I have never seen democracy as vital as in a country that’s only heard of it. On every street corner there was a candidate shouting slogans from a haycart, or 20 people who decided to turn themselves into a rally. Lisa and I arrived in this hurly-burly at about 8 pm, too late to get any dinner anywhere. So we wandered into a beer hall—a gigantic hogan of a thing—and asked whether we could get a drink. The doorman asked if we were Americans. Lisa said yes. The next thing we knew the doorman was shouting, “We have Americans!” and everyone was buying us pilseners, feeding us sausages, and clapping us on our withering shoulders. As we looked bewilderedly at each other, I noticed the posters of American GIs all over the walls. “Is today the 45th anniversary of the American liberation of Pilsen?” I asked no one in particular. More beer! Turns out those Czechoslovakians had liked Americans for a half century, and we were just the first ones that they could buy a drink.

Other Contenders: the 1960 presidential election, a swirl of MLK, Sinatra, the mafia, and a perspiring Richard Nixon; the 1994 multiracial election in which Nelson Mandela became South Africa’s first black president; California’s 2003 gubernatorial recall election, an insane free-for-all in which attracted all sorts of bizarrely proportioned candidates—and one of them won!; Barack Obama’s most fortunate election—no, not “that one,” which unleashed Sarah Palin on an unsuspecting world, but rather his 2004 Senate race in Illinois, in which he battled a candidate who tried to make Borg babe Jeri Ryan have sex in public and, even stranger, Alan Keyes.