Rating President Obama's biggest speeches

President Obama's best speech moments
President Obama's best speech moments

    JUST WATCHED

    President Obama's best speech moments

MUST WATCH

President Obama's best speech moments 03:02

Story highlights

  • Experts weigh in on President Obama's best speeches, offer advice to Donald Trump

(CNN)There's been a lot of talk about words lately -- like "Make America great again" and "Yes we can."

Not really the words themselves, but how they were delivered.
As Barack Obama wraps up eight years of presidential speeches, where every word can move markets and change lives, Trump has been rewriting the rule book.
    "The Trump election has made the case that presidential rhetoric needs to respond to Americans who are looking for a different way to communicate — how you can connect with them on their turf," said Marie Danziger, an expert on speechwriting at Harvard University.
    In other words, experts say, we've entered a new phase in the way presidents talk to the people. The days of ornately written speeches, like the ones history recorded from Lincoln, Jefferson, Roosevelt and Kennedy, are rapidly dwindling in a world where everyone has the attention of a flea and anyone can command their own virtual megaphone online.
    But despite the growing noise, Obama has left a pretty clear legacy of presidential rhetoric. These are the speeches experts rank as the best of his two terms, with an insider's view on how they were crafted.

    1. The victory speech

    Obama first established his reputation as a powerful, influential speaker in 2008, when he broadened his "Yes we can" campaign slogan beyond supporters and invited all Americans to share his commitment to change.
    Obama's 2008 election victory speech
    Obama's 2008 election victory speech

      JUST WATCHED

      Obama's 2008 election victory speech

    MUST WATCH

    Obama's 2008 election victory speech 16:51

    2. Newtown

    He did the same in 2012, this time showing his ability to connect emotionally with the public after the school massacre in Newtown, Connecticut:
    President Obama sheds tears during gun speech
    obama crying gun executive action sot_00004809

      JUST WATCHED

      President Obama sheds tears during gun speech

    MUST WATCH

    President Obama sheds tears during gun speech 01:54
    Several "great speeches of Obama's presidency were after national tragedies, which struck the right note," said author and professor Kathleen Hall Jamieson of the University of Pennsylvania. Many of those addresses were a collaboration between Obama and senior speechwriters Cody Keenan and Terry Szuplat, said former White House staff speechwriter David Litt. "To do that," Litt said, "you have to figure out ways to use some of how you're feeling but also be able to step back for a moment."
    Former Obama speechwriter on gun control
    Former Obama speechwriter on gun control

      JUST WATCHED

      Former Obama speechwriter on gun control

    MUST WATCH

    Former Obama speechwriter on gun control 04:12
    But Jamieson feels like Obama didn't always hit the mark. During his first inaugural address, he failed to digest a core idea into a single memorable phrase — like Franklin Roosevelt did in 1933 with, "The only thing we have to fear is fear itself."

    3. Selma

    On the other hand, Obama did create a history-making moment in 2015 on the 50th anniversary of the civil rights marches from Selma to Montgomery, Alabama, when he delivered an address that many experts said rates among his best.
    "That is a powerful ... beautifully constructed speech," Jamieson said.
    Highlights from President Obama's speech in Selma
    bts obama selma bloody sunday anniversary_00004424

      JUST WATCHED

      Highlights from President Obama's speech in Selma

    MUST WATCH

    Highlights from President Obama's speech in Selma 08:07
    When it comes to putting pen to paper, those who worked with Obama say each speech largely was crafted by the President himself -- especially the important ones.
    "He's a better writer than his speechwriters," said Adam Frankel, a senior Obama speechwriter from 2007 through 2012. "He's probably the most gifted writer in the White House since Lincoln or JFK."
    Unlike President John Kennedy's artistic style, which might have distracted from the underlying emotion in the message, Jamieson said, Obama's crafting has been so stealthy that listeners could be more easily moved by the speech's content.
    The 44th President approaches writing with "his own original, unencumbered style, free of conventional thinking," Frankel added. He captures "thoughts as distinctly as possible. Using phrasing that is appropriate to the occasion, but not typical."

    4. Obama's farewell address

    According to Obama's former writers, the process to create a speech usually goes like this: First, there's an initial conversation between the President and his top speechwriters. They discuss their target audience and what the message should be. Ultimately, they aim to tell a compelling story that people will remember.
    Next, Obama's chief speechwriter would talk with other writers about how to frame the story. For example, shortly after the 2016 election, chief speechwriter Keenan met with staffers to figure out how to write Obama's final address to the nation.
    This meeting was actually captured in the CNN Films' documentary The End: Inside the Last Days of the Obama White House, airing Wednesday at 9pm ET/PT.
    Inside a meeting of Obama's speechwriters
    Inside a meeting of Obama's speechwriters

      JUST WATCHED

      Inside a meeting of Obama's speechwriters

    MUST WATCH

    Inside a meeting of Obama's speechwriters 02:09
    First drafts would go through policy experts and back to the President for final edits or approval. Several weeks later, that meeting resulted in Obama's farewell address, which was delivered to thousands of cheering supporters in his adopted hometown of Chicago, where his "Yes we can" slogan transformed into "Yes we did."
    President Obama says goodbye
    President Obama says goodbye

      JUST WATCHED

      President Obama says goodbye

    MUST WATCH

    President Obama says goodbye 04:01
    "President Obama has always been better speaking to live, large crowds than he has been when speaking to audiences from the Oval Office," says Jamieson. The farewell speech ended up being "deeply optimistic at a time when Hillary Clinton's supporters are not. They needed to hear that optimism."

    5. Reaching out to Muslims in Cairo

    Experts mentioned other standout examples of well-written Obama speeches, such as his Cairo address in Egypt when he reached out to the Muslim world ...
    Obama's 2009 Cairo speech: A look back
    Obama's 2009 Cairo speech: A look back

      JUST WATCHED

      Obama's 2009 Cairo speech: A look back

    MUST WATCH

    Obama's 2009 Cairo speech: A look back 03:31

    6. Obama's 2008 national address on race

    ... and his "More Perfect Union" 2008 campaign speech about America's long rstruggle with racial issues.
    2008: Obama addresses race in America
    2008: Obama addresses race in America

      JUST WATCHED

      2008: Obama addresses race in America

    MUST WATCH

    2008: Obama addresses race in America 05:05
    While some writers get "locked in flourish," said former Obama staff speechwriter Aneesh Raman, the President's writing style "is always pretty direct."
    Former White House staff speechwriter Aneesh Raman works with President Obama aboard Air Force One in 2014.
    During Raman's two years as a White House staff speechwriter, he didn't often meet with President Obama face to face. But the President did edit Raman's draft speeches and send them back with handwritten notes in black or blue ink.
    "When you get handed notes as a speechwriter you can fall victim to the illegibility of someone's handwriting — but his was always legible," said Raman, who now helps high school students raise college scholarship money at an outfit called Raise.Me.
    "His handwriting is very small and neat," said Frankel. "His edits are extraordinarily precise. He may rewrite something the way he wants it and also restructure paragraphs that he thinks are out of order."

    Experts offer advice to Trump

    President-elect Trump and his speechwriters are hammering out what will be one of the most important speeches of his -- every -- presidency: the inauguration speech. Lincoln and Kennedy are still remembered for theirs, so you know -- no pressure.
    If Jamieson could offer Trump a few tips for his inauguration speech, this is what she'd advise:
    • During the speech, identify principles that Americans all share, not ones that divide us.
    • Don't offer specific policy proposals (for example, don't get the audience to chant "Build a wall, Mexico will pay for it").
    • Suppress all campaign tendencies and move into the persona of a president and elevate the audience.
    And about Trump's tweets: Jamieson recommends "falling silent for at least a day after inauguration, to let the address settle in."
    Not that speechwriters have any qualms with using the social platform. Obama's writers saw the rise of Twitter as a legitimate presidential communications tool, said Litt.
    "We certainly saw this in President Obama's second term, there are more and more platforms and you have to be able to not just pick the right message but pick the right way to deliver that message" — whether it's a speech or a tweet.
    "You can say a lot in 140 characters," Jamieson suggested. "Use this format to be presidential. Mr. Trump, find a way to do that."