An Arizona sheriff, a rape victim, a firearms industry representative and a prominent veteran's wife pressed the President over his gun control push during the "Guns in America" town hall moderated by Anderson Cooper and aired by CNN.
The setup, on the campus of George Mason University in Fairfax, Virginia, gave Obama an opportunity to sell his executive actions on gun control, but also face tough questions from opponents who asked him directly how he is working to make Americans safer.
Obama entered office as the candidate who promised to change Washington.
Yet there he was Thursday night, straining to convince his sometimes-skeptical audience just how modest and incremental his executive actions are.
He re-affirmed Americans' right to buy guns, and even said his wife, Michelle Obama, turned to him while the two drove through Iowa during the 2008 campaign and said if she lived in a farm house with a sheriff's office far away, "'I'd want to have a shotgun or a rifle to make sure I was protected and my family was protected.'"
"And she's absolutely right," he said.
When Colorado rape victim Kimberly Corban said that owning a firearm makes her feel safer, Obama told her there is, "nothing we're proposing that prevents you or makes it harder for you to purchase a firearm if you need one."
When Taya Kyle, the widow of "American Sniper" Chris Kyle, pressed Obama to explain America's statistical drop in murders while gun ownership is at an all-time high, Obama compared his actions to adding seat belts and air bags to automobiles, as he said "it takes 20 or 30 years" but eventually America gets safer.
2. He had to admit his limits
As desperate as Obama is to curb gun violence, he had to tell a friend he's known most of his life -- a Chicago priest who pleaded to make gun registrations more like vehicle registrations -- that he's largely powerless when it comes to sweeping changes.
"That's an area where there's just not enough national consensus at this stage to even consider it. And part of it is is people's concern that that becomes a prelude to taking people's guns away," Obama said. "Part of the challenge of this is that the gun debate gets wrapped up in broader debates about whether the federal government is oppressive and there are conspiracy theories floating around the Internet these days all the time."
He told a teen from Chicago: "This is not a proposal to solve every problem. It is a modest way of us getting started on improving the prospects of young men and young women like you the same way we try to improve all the other aspects of our lives."
3. Obama calls fear of his actions a 'conspiracy theory'
It took Anderson Cooper's prodding about the amorphous sense of gun-rights advocates that Obama's true intent is to ultimately take people's guns away for the President to drop his professorial persona and turn angry.
Mark Kelly, the astronaut and husband of former Arizona congresswoman and shooting victim Gabrielle Giffords, told Obama the two gun control advocates have encountered fears that expanding background checks "will lead to a (gun) registry, which will lead to confiscation, which will lead to a tyrannical government."
"With 350 million guns in 65 million places, households ... if the federal government wanted to confiscate those objects, how would they do that?" Kelly asked.
Cooper jumped in, asking: "Is fair to call it a conspiracy? I mean, a lot of people really believe this, deep down -- that they just don't trust you."
"I'm sorry, but yes, it is fair to call it a conspiracy," Obama said. "What are you saying? Are you suggesting that the notion that we are creating a plot to take everybody's guns away so that we can enforce marshal law is a conspiracy? Yes, that is a conspiracy. I would hope you would agree with that. Is that controversial?"
He said if he truly desired to strip away Second Amendment rights, he'd have started much earlier in his presidency.
"Look, I mean, I'm only going to be here for another year. I don't know -- when would I have started on this enterprise, right?" Obama said.
4. It's all on him
Obama was critical of the National Rifle Association and its grip on the Republican-led Congress. "The way we break the deadlock on this issue is when Congress does not have just a stranglehold on this debate -- or, excuse me, the NRA does not have a stranglehold on Congress in this debate," he said.
He called out Congress for failing to embrace his call to ramp up funding for Bureau of Alcohol, Tobacco, Firearms and Explosives agents -- underscoring the central problem Obama faces: Congress isn't going to touch that issue, nor anything else he pushes connected to gun control.
Obama's comments about the ATF -- "they have been portrayed as trying to take people's guns away as opposed to trying to make sure that the laws are enforced" -- could just as easily have described how the president believes his opponents view him.
But on gun control, he can't even pick a fight. At least not in person.
The NRA declined CNN's invitation to participate in Thursday night's town hall. And at the same time Obama ripped them, chief NRA lobbyist Chris Cox was appearing on Fox News, hammering Obama in an interview with Megyn Kelly.
When host Megyn Kelly asked whether Cox would take Obama up on his offer to meet with the NRA, Cox responded: "And talk about what, Megyn? ... He doesn't support the individual right to own a firearm."
5. The tears of Sandy Hook
When CNN played the clip of Obama shedding tears during a White House speech this week over the deaths of elementary-school children in Newtown, Connecticut, five years ago, Obama admitted he surprised himself with the show of emotion.
That massacre, though, crystallized the gun battle in Obama's mind -- and shows why he'll never drop it, no matter the politics.
"It's the only time I've ever seen Secret Service cry, on duty," Obama said.
"It continues to haunt me. It was one of the worst days of my presidency."