This year's Stand Up for Heroes, which took place Wednesday night, was the 11th edition of the comedy benefit for wounded veterans but the first under the Trump administration, with last year's event taking place a week before Election Day.
Regular performer Jon Stewart even made light of the past year by musing, "Last time I was here, I can't remember what happened. It was before the election, and I sort of blanked out. What happened? Anything exciting? Did my candidate win?"
As commander in chief, Trump called for a ban on transgender people serving in the military, and he's had at least two disputes with the families of fallen soldiers, one during his presidential campaign. So how did political comedians like Stewart, John Oliver and The Daily Show's Trevor Noah and Hasan Minhaj feel about taking on the current president in a room full of veterans?
Speaking with The Hollywood Reporter on the red carpet ahead of the event, which kicked off the 2017 New York Comedy Festival and was presented by the festival and the Bob Woodruff Foundation, Oliver said he wasn't worried about biting his tongue.
"I think people, with people in the military, they often think they can't handle jokes, but they're not as sensitive as people are concerned about sometimes. You can joke about anything," he said. "I did a USO Tour. I was kind of worried before that, wondering what is and isn't appropriate and then you get over there and you realize that anything's appropriate, they just want to laugh."
Minhaj, meanwhile, said he was choosing to focus on how he can help wounded veterans, which he sees as a nonpartisan issue.
"I can still control what I do and the narrative that I share, and I think it's a uniquely American perspective and that that brings us together is what I'm sort of focusing on like, 'No, no, no we're not going to let any sort of identity politics divide us.' This is about helping injured troops and people that need care and services, and to me that's not a partisan issue and for me, fighting for that is the most American thing you can do," Minhaj told THR. "As weird as that sounds—I'm going to be subversive by fighting for veterans. It's weird to say that but that's my way of saying, I'm going to recenter the narrative."
And despite Woodruff Foundation co-founder Lee Woodruff telling the crowd to "set aside politics" at the top of the evening, a number of the comedians did indeed take aim at the president, with Conan O'Brien comparing him to an orange cat's rear end as the TBS host rattled off the cast for a fake movie about New York.
Stewart kicked things off and wasn't shy about going after Trump, even though he did observe out loud at one point, "Yeah, I know where I am. Don't worry about it. I know the crowd I'm in."
The former Daily Show host focused on a statistic "that 10-15 percent of Obama voters voted for Trump," Stewart said, struggling to comprehend how people could support both politicians.
"How does that happen?," Stewart wondered before imagining such a voter's line of thinking. 'You know who I really want to vote for, you know who I really love, is that very staid professorial gentleman from Kenyan birth who has an articulate sense but a bit standoffish and aloof, intellectual, professorial—that's the guy that I really love, but you know since he's not running this year, I'm gonna check out the grab 'em by the pussy candidate. That seems like a good natural evolution of my political [beliefs]' How do you even get there?"
He added, "It's like a guy who's like, 'It didn't work out with my girlfriend, so now I'm going out with a toaster.' Just stick my dick in it and see what happens. That's really I think where our country's at right now. We all put our dick in the toaster and we're all waiting to see what happens."
Later Stewart's former Daily Show colleague John Oliver likened the current state of America to "a girl who's throwing up all over herself," putting those who love and support the U.S., like the British comedian, in the position of "holding her hair back, saying, 'Let it all out. You just made a mistake, that's all. You can't repeat this mistake though otherwise you become less sympathetic.'"
And he reassured audience members that the country will "be fine," "at the other end of what it's going through right now."
"While that's basically baseless, here's why I think it's true: Because you will make it so. America is a defiant nation. You are the most defiant nation on Earth," Oliver said.
Earlier current Daily Show host Trevor Noah said he found Trump to be "an emotional paradox."
"I don't know how to feel about him. On the one hand, I do wake up terrified most days at the notion that he's president of the most powerful nation in the world," Noah said. "But, on the other hand, I must admit I wake up every day knowing he's going to make me laugh. I cannot deny these two things are true. There's terror and there's joy. You know what it feels like? It feels like there's a giant asteroid headed toward the Earth but it's shaped like a penis. I think I'm gonna die, but I know I'm gonna laugh."
He also speculated that Trump might "quit during his term," not even for political reasons.
"He doesn't live by the rules. He does his own thing. I'm surprised he subscribes to gravity. He does whatever he wants," Noah joked. "I wouldn't be surprised if Donald Trump quit after two years, and he just walked out of the White House and was like, 'Unlike most presidents, I did it in half the time, folks. So much faster.' People are like, 'Why is he doing this?' Because he said he was going to do it. He said he was going to shake things up. Are things not shaken? Are you not entertained?"
And he praised Republicans for their skill at "political branding."
"Democrats, nice people, no clue about branding. 'Resist!' 'What are we resisting?' 'Everything.' There's no specificity, no emotion," Noah observed. "Republicans connect with you on all the issues — powerful — gun control — you feel it, they're gonna control your guns. Pro life or pro choice? You feel the stakes."
It wasn't all political comedy, though. John Mulaney had the Theater at Madison Square Garden crowd laughing with his jokes about assemblies, police sirens and humans having to prove to computers that they're not robots. And the Red Hot Chili Peppers closed the show with a high-energy set, taking the place of regular musical performer Bruce Springsteen, who had performed at the past 10 editions of the event but was unavailable this year because of his Broadway show.
And O'Brien, returning after hosting the first Stand Up for Heroes in 2007, also made the evening's only reference to the wave of sexual assault and harassment allegations sweeping through Hollywood. As he read off the cast list for his fake New York movie, with such selections as David Spade playing Megyn Kelly, Young Sheldon star Iain Armitage playing Rachel Maddow, O'Brien said Harvey Weinstein would be played by "the Mucinex monster."
"The Mucinex monster is offended," O'Brien said after the mere mention of Weinstein's name drew loud boos from the audience. "How dare you."
Stand Up for Heroes, has raised more than $40 million since it began in 2007 to help injured service members and their families. This year's event raised more than $5.3 million for the Bob Woodruff Foundation.