Last week’s Republican National Convention provided a powerful reminder that while most political speeches are rarely memorable, the really bad ones tend to be unforgettable.  Actor Clint Eastwood’s primetime conversation with a chair—who he referred to as the invisible President Obama—became an instant twitter hit, with @InvisibleObama  becoming a twitter handle before night’s end. (At last count the account has over 68,000 followers.) It also turned the long admired actor known for his tough guy persona into an object of ridicule. Democrats and Republicans who agree on little else were virtually unanimous: the speech was a dud, the kind of dud that will be remembered for years to come for all the wrong reasons. But the spotlight Eastwood and his chair generated raise an age-old question. What makes a good speech? And what does President Obama have to do Thursday night to leave Americans convinced that he made one?

According to Doug Gordon, Managing Director of Fitzgibbon Media, a leading progressive communications strategy firm, “convention speeches that breakthrough have grand themes, for the audience following at home, as well as
memorable one liners.” He pointed to examples such as the late senator Ted Kennedy's speech at the 1980 convention, President Obama’s speech at the 2004 convention and Gov. Sarah Palin's speech at the 2008 convention which spawned the oft-referenced line, "The difference between a hockey mom and a pit bull? Lipstick."

 Dan Gerstein, Founder of Gotham Ghostwriters, which specializes in helping high-level clients craft and deliver winning speeches said there are countless small details that can help make the difference between a winning speech and one that bombs. The most important advice he would give any client, however, is what he called “the oldest speechwriting maxim in the book — show, don't tell.” In the case of President Obama he said that means, “Show the public you are thinking about them, their future, and what you are going to do to make it better.”

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To Gordon and Gerstein’s points, history’s most celebrated speeches tend to emphasize hopes that extend beyond the person giving it, and a theme that looms larger than the moment in which the speech is being given. Martin Luther King Jr.’s “I Have a Dream” speech and President Obama’s star making speech at the 2004 Democratic National Convention both emphasized the greatness of America, and their desire to see our country become even greater, for the benefit of all Americans and in the interest of securing a more promising American future.

But King and Obama’s speeches also have something else in common: they were delivered by two of history’s most acclaimed speakers. Even President Obama’s critics acknowledge his gift as a speaker, with “articulate” being a common adjective used to describe him. But with an entire election at stake simply being eloquent may not be enough.

Gerstein, Gordon and political consultant Basil Smikle all agreed that the President’s speech needs to be both inspiring, but also substantive in articulating key messages, among them that he has a clear plan for addressing the economy if given a second term. But Smikle added that, “while his speech should be motivating and reassuring to Democrats, it should really be geared toward disaffected voters -especially Independents.”

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This is particularly challenging because as Gerstein pointed out, those most likely to watch conventions are those most interested in politics and a specific political party, which means in some ways the president will be preaching to a choir. But Gerstein added that media coverage of key highlights of a speech can have an impact and reach those not watching the convention, something the heavy coverage, and praise, of Michelle Obama’s convention speech proves. According to Gerstein, this leaves the president with quite a balancing act: he must fire up loyal democratic voters watching who are enthusiastic about some of his more partisan policies, without alienating the very independent voters Smikle notes he needs to reach.

A tough act, for sure, but not impossible, particularly for someone Gordon dubbed one of “the best orators” there is. But ultimately, the experts agree that speeches don’t win elections, the overall package of a candidate does. This means that a speech essentially becomes one chapter in helping to tell the story of a candidate—albeit an important one. History is littered with great orators who ran for president and never won, among them the Rev. Jesse Jackson and Sen. Ted Kennedy. But  Gordon acknowledged that today’s social media landscape means that the impact of a great speech, or bad one can be felt more immediately, and spread virally in a way that did not exist in previous campaigns.

This is why news outlets declared, “Twitter Elects Michelle Obama President of Speeches,” following the First Lady’s convention triumph while “Eastwooding,” in which people took photos with empty chairs, became an instant online meme, and an embarrassing online souvenir of the Republican National Convention. So if President Obama delivers the speech of his life, one that inspires the hopes and dreams of Americans, while simultaneously reassuring them of his competence in handling the economy, and also drawing sharp contrasts between his opponent, he may not automatically win the election, but he may win the news cycle, and that is almost just as important.

Of course he has some serious competition to win the campaign communications showdown and so far it appears the president might end up losing his oratorical crown—-not to his opponent Mitt Romney, but to his wife whose convention speech this week has many believing that the president may not be the most articulate Obama after all.

Keli Goff is The Root’s special correspondent. Follow her on Twitter