John Avlon is a CNN senior political analyst and anchor. The opinions expressed in this commentary are his own. View more opinion articles on CNN.

(CNN)Great political debates are usually defined by candidate answers that crystalize a campaign (“Are you better off now than you were four years ago?”) or sound bites that leave an opponent gasping on the canvas (“Senator, you’re no Jack Kennedy”).

John AvlonJohn AvlonJohn AvlonThe art of asking questions in the debate is less celebrated but equally essential. CNN’s Wolf Blitzer, who has moderated more than his share of political rodeos, told me: “a great question showcases a substantive and important policy difference between the candidates. The goal is to give voters a better appreciation where the candidates have disagreed.” The right question at the right moment can reveal character, cut through spin with devastating clarity, and help voters make decisions armed with facts rather than fears.So as you pregame this week’s CNN debates, digest this selection of some of the best presidential debate questions ever asked. 1988: Bernard Shaw to Michael Dukakis Roaring out of the gate, like Mike Tyson’s first round demolition of Michael Spinks, CNN’s original primetime anchor Bernard Shaw stripped Michael Dukakis bare with this brutal opening question: “Governor, if Kitty Dukakis were raped and murdered, would you favor an irrevocable death penalty for the killer?”Read MoreWanted: some non-toxic masculinity from DemocratsWanted: some non-toxic masculinity from DemocratsWanted: some non-toxic masculinity from DemocratsThe Duke played it cool and that was the problem. “No, I don’t, Bernard,” he said. “And I think you know that I’ve opposed the death penalty during all of my life.” He seemed more Vulcan than American.In a perfect world, Dukakis should’ve shown a flash of anger and then used that to explain that those emotions are exactly why we must be a nation of laws, not men. Instead, it solidified his reputation for caring more about criminals’ rights than victims’ rights.As jaws dropped watching the political vivisection on live TV, the Dukakis campaign manager, Susan Estrich, knew it was all over. “It was a question about Dukakis’ values and emotions,” she recounted. “When he answered by talking policy, I knew we had lost the election.” 1976: Max Frankel to Gerald Ford The most important question is often the follow-up — and it’s the punch that too many moderators miss, sometimes for fear of seeming rude, sometimes because they don’t have the knowledge confidently in hand.That was definitely not the case with Max Frankel in 1976, when the Pulitzer-Prize winning New York Times journalist leveled the playing field between incumbent Gerald Ford and challenger Jimmy Carter. Quick on his feet, Frankel called out the President with a clarification after Ford said, “There is no Soviet domination of Eastern Europe.””I’m sorry, what?,” Frankel said, with something close to a Belushi-esque eyebrow raise. “Did I understand you to say, sir, that the Russians are not using Eastern Europe as their own sphere of influence in occupying most of the countries there and making sure with their troops that it’s a communist zone?”Ford stuck by his misstatement, abiding by the diplomatic fiction that the countries behind the iron curtain were autonomous. But suddenly the Republicans traditional advantage on national security evaporated and a peanut farmer turned one-term Georgia governor didn’t seem like such a gamble. 1960: Sandor Vanocur to NixonMaking candidates confront uncomfortable facts is a key role for debate moderators. That’s what NBC’s Sandor Vanocur did during the pivotal first Kennedy-Nixon debate. He aimed at the heart of Nixon’s election argument — superior executive experience at the right hand of President Dwight Eisenhower over eight years — by asking the vice president about a notably cold comment from Ike.Bottom line, 2020 Dems are in a contest defined by raceBottom line, 2020 Dems are in a contest defined by raceBottom line, 2020 Dems are in a contest defined by race“Republican campaign slogans, you’ll see them on signs around the country as you did last week say, ‘It is experience is that counts,’ that’s over a picture of yourself sir implying that you have more governmental executive decision-making experience than your opponent,” Vancour said in the circuituous, almost-courtly tone of the time. “Now in a news conference on August 24, President Eisenhower was asked to give one example of a major idea of yours that he had adopted. His reply was, and I am quoting, ‘If you give me a week I might think of one. I don’t remember.’ Now that was a month ago sir, and the President hasn’t brought it up since and I’m wondering, sir, if you can clarify which version is correct — the one put out by Republican campaign leaders or the one put out by President Eisenhower.”Nixon stammered a bit about how the President was being “facetious” while the sweat beaded up on his Lazy Shave. But Vanocur’s question provided a substantive gut punch that undercut the candidate’s core claim and shaped the television audience’s perception that Nixon lost the first debate on style points. 2016: Megyn Kelly, Anderson Cooper and Donald TrumpIt was not exactly a secret that Donald Trump had a problem with women. But Megyn Kelly went there during the first GOP primary debate, launching into the question. “You’ve called women you don’t like fat pigs, dogs, slobs and disgusting animals. Your Twitter account …”Trump broke in and said, with finger raised, “Only Rosie O’Donnell.” This brought the house down, causing Dilbert cartoonist and semi-professional Trump fan Scott Adams to declare the candidate a “master persuader.” Trump pivoted his answer to criticize political correctness and kicked off a brief feud with Fox News. In October, the Access Hollywood Tape dropped, showing Trump bragging on mic about grabbing women because “when you’re a star they let you do it.”CNN’s Anderson Cooper hosted the next presidential debate with Martha Raddatz and tried to push the nominee past his dismissal of the tape as “locker room talk.” “You described kissing women without their consent, grabbing their genitals. That is sexual assault,” Cooper said. “You bragged that you have sexually assaulted women. Do you understand that?”Stay up to date…

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Trump bobbed and weaved, saying it was “locker room talk” and he had apologized for it, but Cooper forcefully followed up three more times. In his instinctive bid to distract and deflect, Trump complained they should be talking about more important things. But sometimes scandal is substantive.For candidates, the debate moments that endure are often unrehearsed — for better or worse. But those indelible moments are built on tough, smart questions. It’s an art worth appreciating as you sit down to make an informed citizen’s decision about the direction of our democracy.

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