What was the greatest speech of Barack Obama?

I consider Obama's speech honoring Clementa Pinckney at his funeral in Charleston at Mother Emmanuel to have been one of the more remarkable speeches ever given by a sitting president. It honors the man and is a remarkable example of Obama's ability to bring an appropriate and meaningful speech on the occasion of the massacre in South Carolina. And, remarkably, he ends it by singing Amazing Grace, grace having been the major theme of the eulogy.

So many to choose from, but my personal favorite was his speech on race in March 2008. Then Sen. Obama's Chicago pastor Jeremiah Wright had gone on an unrelenting press tour after videos of ever increasingly radical sermons had surfaced on YouTube. (It's worth noting that 2008 was the first Presidential race with YouTube, an element that democratized the news cycle in ways we are still learning from.)Many expected the Senator to follow the campaign "playbook" and throw him under the bus as soon as possible. That is, conventional wisdom said he should immediately get in front of a bunch of cameras and disavow all comments said by Rev. Wright and any relationship with him. What he chose to do was something different:He waited several days, wrote his own thoughtfully worded speech on the subject, and more or less paused his involvement in the campaign to get this speech right. The media had tried to engage him in a conversation on race, and he had avoided doing so because he didn't want his comments distilled into sound bytes. He seized this opportunity to lay out his thoughts on how the Black experience is reflected through the Black church. As a white man, I appreciated how the imagery he used allowed a peak into life in Black America. The particular point that hit me was when he said that the most segregated hour of the week in America happens on Sunday morning. This speech answered a large bank of curiosities America had about Sen. Obama's thoughts on race relations, and it could have been a great and classy end to the story of Rev. Jeremiah Wright. Unfortunately, after this speech, Wright continued his press tour, making comments that some of which many believed to be racially insensitive, and others were thought to be straight up antisemitic. Some colleagues of mine even suggested that Rev. Wright was actually a Hillary supporter doing what he could to end Sen. Obama's campaign. After it became clear that this was not going away, Sen. Obama eventually denounced Rev. Wright outright, and joined the Metropolitan AME church in DC.

There's also his speech at the 2004 Democratic Convention. Highly recommended. 

I was particularly touched by his speech upon winning his first Presidential election at Chicago. The imagery he used of an elderly African American lady who had gone through all the discrimination and culminating in her pressing on a screen to cast her vote, and his election as the first African American president, left a great impression in my mind. It reminds the audience of how long a journey progress has taken but that it is possible. "The arc of the moral universe is long, but it bends towards justice."

A2A,First, some disclosures: I'm not the biggest fan of Obama, so I'm going to offer the sort of 'contrarian' view on his speeches ... I fully acknowledge that Obama is a good speaker [many of his Press Dinner speeches, for example, have been fantastic], but frankly I don't think he's really given that many 'Iconic speeches' that will be much remembered in 10 years ...[And lest you all think I'm just some thoughtless Obama hater, I would, for example, posit as a counter-example that George W. Bush only gave one good speech during his entire Presidency - the 'Axis of Evil' speech; It was so good it effectively started a war! ... and how'd that turn out?]To my mind Obama's got two really good speeches under his belt:The first is his "address to the 2004 Democratic Convention". This speech essentially launched him on the national stage, and gave many the feeling that he had the 'royal jelly'; many even wondered aloud if the D's had the wrong nominee!I think his second great speech was the "Jeremiah Wright" speech, about religion, during the 2008 election. People forget how devastating the growing effects of his linkages with this man were during the campaign. And in one single speech Obama a) essentially shut down this entire issue, b) made it radioactive to attack him about his personal life and religion, c) negated "Rev. Wright" from further damaging his campaign and d) (why it's a great speech) said several things that cut to the heart of the American ethos, and prejudices, about religion, and (especially) actually changed many people's minds about what was being said. Essentially, he both cut into the heart of the American psyche and simultanously saved his campaign with this speech.( As a 'runner-up' speech, I'd offer: his "2008 election night victory" speech. In this speech he essentially affirmed that a Black man, a person of color, had finally ascended to the highest office in the land, and that some part of the American vexation regarding race had finally been broken. )( Also, as a non-gracious parting shot: Obama's also had some truly horrible speeches, especially in the policy sense (which is where I strongly differ with him) (and yes, several of these speeches were 'well delivered'), but the content was, IMHO, menacing and dreadful!  There's too many examples for me to offer here ... but a brief synopsis: a) haranguing the Supreme Court in the State of the Union, b) lecturing and belittling Paul Ryan, about his earnestly offered policy proposals, while he sat in the front row, leading up to the budget debate (this destroyed almost all possibility of bipartisan compromise)** and, 3) (as a last example) his speech about individual success in America -- aka the "You didn't build that" speech -- which still makes my blood boil even today. -- Infuriating words well delivered still infuriate! )Hope that helps.Notes: ** lest someone want to come back on me about this episode: Several of my close friends, themselves staunch Democrats and longtime DC operatives were actually at the event where Obama lectured Paul Ryan about his proposals; and they themselves were furious about what Obama had done. One said: "It's the most despicable thing I've ever seen in Washington." Another said: "It was horrible ... everyone in the room just wanted to die ... it was disgusting..."

I myself would say the keynote address speech that he gave at the DNC in 2004, when Kerry was the Democrat nominee. I remember wondering "who is this guy, and why isn't he himself running for president?"

You could look at this one two ways: either he lost decorum and that was tacky, or you could revel in the fact that he shamed the Supreme Court bench at his State of the Union about Citizens United. The bench's reaction is kinda funny, and you can take glee in the whole thing. Look up 2010 SOTU on Youtube.