FAIL: Michael Dukakis’s ‘Weak’ Death Penalty Answer

If your wife were raped and murdered, would you want the perpetrator put to death? That was the question put to the Massachusetts governor during the 1988 presidential debate, about his wife, Kitty. “You know that I’ve opposed the death penalty during all of my life,” Dukakis said. Wrong answer—the Democratic nominee was seen as weak and ultimately lost the election to George H.W. Bush. Years later, Dukakis looked back on his answer and still didn’t understand what was so wrong with his response. “I have to tell you, and maybe I’m just still missing it,” he said. “I didn’t think it was that bad.”

WIN: Ronald Reagan’s ‘There You Go Again’ Zinger

Mitt Romney may be trying to capture a bit of Ronald Reagan’s 1980 magic, which helped the onetime California governor defeat incumbent President Jimmy Carter. But let’s hope Romney isn’t trying to craft a line reminiscent of Reagan’s famous “There you go again,” slipped into this debate on Medicare—because the Gipper says that he just made it up on the spot. “It just seemed to be the thing to say,” Reagan told Jim Lehrer nine years later.

FAIL: George H.W. Bush’s Ill-Timed Watch-Check

This might be a good question to ask this time around. “How has the national debt personally affected each of your lives?” a voter asked in 1992. President George H.W. Bush was slated to answer first, and he decided to check his watch as the voter described her struggles in the country’s weak economy. It was time for you to pay attention, Mr. President. Big mistake. Challenger Bill Clinton, meanwhile, began his response by asking the voter to repeat how she had been affected. (In all fairness, perhaps Bush just has a tendency to check his watch at inopportune times; in 2008, as his daughter-in-law Laura addressed the Republican National Convention, he checked his watch again!

WIN: Ronald Reagan’s ‘Youth and Inexperience’ Quip 

Another Gipper gem. When challenged on his age in a 1984 debate with challenger Walter Mondale, Reagan joked that he was “not going to exploit, for political purposes, my opponent’s youth and inexperience.” At 73, he still had it, and he won in a landslide.

FAIL: Gerald Ford’s Soviet Union Gaffe

Remember when the Soviet Union controlled Eastern Europe and imposed—through military force—a communist ideology deeply antithetical to American foreign policy? Of course you do. Well, President Gerald Ford did not. In October 1976, Ford faced off against Georgia Gov. Jimmy Carter in a debate and declared: “There is no Soviet domination of Eastern Europe.” Moderator Max Frankel of The New York Times followed up, smirking, and gave Ford a chance to walk back his statement. Instead, Ford doubled down and asserted that Poland, Romania, and Yugoslavia were free of Soviet influence. Then he lost the election.

WIN: John F. Kennedy’s Mattifying Makeup 

In 1960, John F. Kennedy and Richard Nixon participated in the first ever televised presidential debate. Nixon refused to wear makeup. Kennedy did, and was much better looking. The end.

FAIL: Al Gore’s Lame Intimidation Attempt

Amid rumors that Al Gore was receiving “alpha male” training in preparation for his debates against George W. Bush, the Democratic candidate tried to go toe to toe with Dubya—and got embarrassed. Gore stood up to challenge Bush in this 2000 debate, but got flummoxed and deflated by a simple nod.