From pop stars to insult comedy, the Dems threw a cookout where the real joke was on Trump

Since the Clinton era, the Democratic Party has claimed the concept of political rock stars. Following 12 years of Democratic candidates and two Republican presidents who either looked like your dad or your grandpa, Bill Clinton and Hillary Clinton had disaffected young voters humming the refrain to Fleetwood Mac’s “Don’t Stop.”

We wouldn’t see his like again until Barack Obama spoke at the 2004 Democratic National Convention, putting the wiring in place for 2008 when the mic passed to him. Eight years later Democrats had four rock stars pitching to the American people – one of whom, Hillary Clinton, ran for the top office and lost to a blustery showman.

In the years since Donald Trump won office, and the four since he lost, Democrats watched the world shift. Fewer rock stars can sell out stadiums or arenas these days. They ceded that ground to comedians, especially ones who hit below the belt and shrug off protests about their cruelty by decrying cancel culture and supposed “wokeness.”

Trump was good for those guys. He opened the market for “putting it out there” or “saying what everybody’s thinking.” But here’s the thing about markets – when they get flooded, demand plummets. Trump’s material never changed. Grievance is exhausting.

If the recently ended convention felt vibrant and energizing, that may be a sign the audience is ready to shrug off autocratic doom.

So the Democratic National Convention turned Chicago’s United Center into the world’s biggest cookout.

Was that Don Cheadle chilling in the stands? Why yes it was. Oprah Winfrey, ladies and gentlemen, was a surprise speaker. Sean Astin introduced Indiana’s delegates, and Wendell Pierce repped Louisiana. “Scandal” stars Tony Goldwyn and Kerry Washington reunited to bring up the nieces of the party’s nominee Kamala Harris to teach everyone how to pronounce her name.

Overall, though, these four nights were less about political rock stars than pop power. The roll call had a DJ blasting tracks for each state, stopping the show when Lil Jon bounded in to introduce Georgia’s delegation and drop a few bars “Turn Down For What.” Harris’ home state California got four songs to pledge its delegates’ votes: Dr. Dre and Snoop Dogg‘s “The Next Episode,” Tupac Shakur‘s “California Love,” and Kendrick Lamar‘s “Alright”  and “Not Like Us” (which, you’ll note, is a diss track).

John Legend, joined by Sheila E., perform Prince’s “Let’s Go Crazy” during day three of the 2024 Democratic National Convention in Chicago on Wednesday, August 21, 2024. (Bill Clark/CQ-Roll Call, Inc via Getty Images)

The biggest Thursday rumor was that Beyoncé would roll up, perhaps to introduce Harris, to whom the pop idol gave her blessing to use her track 2016 “Freedom.” That did not come to pass, but it’s not as if the convention was hurting for icons. By the time Harris spoke on Thursday, Pink had performed “What About Us” with her daughter Willow. Before them, The Chicks sang the national anthem.

Prior days featured John Legend and Sheila E. busting out Prince’s “Let’s Go Crazy” to represent Minnesota and performances from Maren Morris, Patti LaBelle, Mickey Guyton, Jason Isbell, Common and Jonathan McReynolds.

And the politicians? The usual parade of star elected officials sauntered past, but this time most opted to forgo the standard stemwinder for a tight five.

There was Bill Clinton on Wednesday calling Trump the “me, myself and I” option: “He mostly talks about himself. . . he’s like one of those tenors, opening up before walking onstage like I did. Trying to get his lungs open by singing, ‘Me, me, me, me, me me!’”

There was House Minority Leader Hakeem Jeffries (D-NY) likening Trump to “an old boyfriend who you broke up with, but he just won’t go away. He has spent the last four years spinning the block, trying to get back into a relationship with the American people. Bro. We broke up with you for a reason.”

Michigan Gov. Gretchen Whitmer derided how out of touch Trump is. “Donald Trump doesn’t know you at all. You think he understands that when your car breaks down you can’t get to work? No. His first word was probably ‘chauffeur.’ You think he’s ever had to take items out of the cart before checking out? Hell, you think he’s ever been to a grocery store? That’s what the chauffeur is for!” 

It’s not as if the other side has been offering up much of a battle for “Last Comic Standing” either. Rarely has there been a riper and more luscious target than Trump as he is now – knocked back on his heels, unsure of how to attack Harris or Walz. His team had plenty of “Your Biden is so old/ “How old is he?” material.

Now, that’s all out the window; now he’s the 78-year-old man struggling to come up with a schoolyard bully nickname for the younger woman he can’t help admitting is pretty by claiming too loudly in Wilkes-Barre, Penn., “I’M A BETTER-LOOKING PERSON THAN KAH-MAH-LAH.”

He was not kidding then, or when picked heckle-bait for his running mate. JD Vance stinks at wisecracks, and Trump hates being mocked. You couldn’t ask for better material.

In 2018 Obama’s former Attorney General Eric Holder contradicted Michelle Obama’s famous slogan by opining that it should be, “When they go low, we kick them.”

Former first lady Michelle Obama speaks on stage during the second day of the Democratic National Convention at the United Center on August 20, 2024 in Chicago, Illinois. (Andrew Harnik/Getty Images)

Tuesday night the former first lady proved she was listening. After reminding the crowd that their experience shows Trump feels threatened “by the existence of two hard-working, highly educated successful people who happen to be Black,” she added, “I wanna know, who’s gonna tell him that the job he’s currently seeking might just be one of those Black jobs?” 

It isn’t beyond imagination to picture Michelle making this quip in 2020 but with a bright smile. In 2024, though, she’s bulked up her stage persona. In the laugh break that followed that joke, she stared directly into the camera, her mouth playfully twisted in a “you know what I’m talkin’ about” half smirk, accessorized with side-eye.

I guess she figured Stevie Wonder had the whole nobility part covered by performing “Higher Ground.”  She wasn’t wrong.

All this aligns with the Harris-Walz campaign’s “joyful warrior” strategy, but it’s also a matter of meeting the opponent on their turf with an “anything you can do, I can do better” attitude.

Right-wing comedy is its own . . . thing . . . but the left understands that classic joke structure still rules. Combining that with the might of punching up, throw in a few live music performances, and you’ve got yourself a viewership draw.

The DNC has a network sitcom dad in Minnesota’s governor and vice presidential candidate Tim Walz, a veteran and former football coach (“ASSISTANT coach,” Trump live whined on Truth Social) who owns guns, hunts and swears that turkey is a vegetable.

Walz’s best set came before the convention, on Aug. 6, when he tossed off a killer jab at Vance’s expense. (“I can’t wait to debate this guy.” Pause. “That’s if he’s willing to get off the couch and show up. See what I did there?”) And that’s fine – every entertainer knows they need to save some gas for their headlining gig.

Former President Barack Obama speaks during day two of the 2024 Democratic National Convention in Chicago on Tuesday, August 20, 2024. (Bill Clark/CQ-Roll Call, Inc via Getty Images)At a comedy festival, you don’t compete with the big guns, and as “Late Night” host Seth Meyers noted this week, everyone’s favorite Barack Obama is stand-up Obama. He did not disappoint, and neither did Michelle. She set ‘em up, and knocked ‘em down, and set him up again. Obama razzed himself by saying, “I am the only person stupid enough to speak after Michelle Obama,” but he did just fine.

All he had to do was pantomime along to a jape about Trump’s obsession with audience counts, positioning his palms in a way that everyone knew he wasn’t referring to inadequacies over rally size comparisons. Then, and this was brilliant, he threw up his hands and looked up and away as if to say, “What, am I wrong?”

There may have been some who might have scolded a former president for – gasp – daring to indulge in ribald, low-brow swipes. Before 2016, we should say. Eight years later, and with just over 70 days until the election, the Democrats are swiping their tormentors’ laugh-at-’em tactics to corner the attention economy — but a version that chooses cleverness.  

The Harris-Walz campaign’s TikTok team is made up of five staffers under 25, The New Yorker reports, which you can tell. The media blasts have insouciance previous presidential campaigns wouldn’t have dared to sign off on.

One includes a post from social media @dril, a very online social media comedian who apparently wasn’t too pleased about the shout-out.

At the convention, however, their most skillful creators didn’t have to try hard to beat Trump’s surrogates wandering around “undercover.” MyPillow huckster Mike Lindell, freshly shorn of his walrus mustache, tried to debate a 12-year-old . . .

OK, can we pause? Just let that sink in.

A-a-and we’re back. Lindell stepped up to 12-year-old content creator Knowa De Brasco, probably thinking he’d score points by owning a child by trying to give him a swirlie with his voter irregularity conspiracy hokum, and ended up getting cooked, turned over and cooked again.

When Lindell blabbed out one anecdote about a “friend,” he wasn’t prepared for De Brasco to ask for that friend’s last name, which Lindell refused to provide.

“Maybe you didn’t see this in the news, maybe you’re not up on things,” Lindell ranted.

“Oh, I am. I’m up on your bankruptcy too, sir,” De Brasco said with a smile, listening politely until he finally stuck a fork in Lindell with, “So your source is ‘Trust Me, Bro’? That’s your source?” Ba-dum-CHING!

The real joke is on Trump. I mean, he started it. Political lore alleges Trump’s career in politics kicked into high gear after Obama and Meyers mercilessly roasted him at the 2011 White House Correspondents’ Association dinner. (An example from Meyers: “Donald Trump said recently he’s got a great relationship with ‘the Blacks,’ Unless the Blacks are a family of white people, I bet he’s mistaken.”)

Cut to 2016: the Democrats thought they could win with a qualified candidate with extensive experience and proficient policy explanations. Then, boom! America voted for an ex-game show host who made crowds laugh with grade-school-level taunts like referring to Sen. Elizabeth Warren (D-MA) as “Pocahontas” and ridiculing a reporter with a disability.

Comedy’s currency had turned to cruelty, and Trump was simply sharing the wealth. Last week his opposing party showed it had been saving up too while also presenting itself as a party of sincerity, featuring gun violence survivors, military veterans and Walz’s former high school students from Mankato, Minn.

But even that was wrapped in pageantry – optimistic, raucous pageantry, but a showcase nevertheless that could avoid steering into a pothole behind the scenes by rejecting the Uncommitted National Movement’s efforts to allow a pro-Palestinian speaker to talk about the Gazans’ plight before the convention audience.

Muslim Women for Harris-Walz immediately disbanded after the DNC said no, citing in part the inconsistency of the party inviting the parents of Israeli hostages onstage while denying the request.

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A reminder, perhaps, of the other type of politics powering this elevated courtship dance with American voters. The Harris-Walz campaign has little time to make its case to the widest swath of American voters, many of whom desire a ceasefire in Gaza but are also pro-military.

Lobbies such as the American Israel Public Affairs Committee (AIPAC) are also pouring tens of millions of dollars into ousting progressive Democrats like Congresswoman Cori Bush (D-MO) and Rep. Jamaal Bowman (D-NY) by supporting their primary opponents’ campaigns.

The final act of the convention, Harris’ Thursday night speech, was as much about laughing with her party and at Trump, who she called “an unserious man,” and a tightrope act.

When it came time to talk about the conflict, Harris quoted the Biden administration’s stance (“I will always stand up for Israel’s right to defend itself”) and added, “At the same time, what has happened in Gaza over the past 10 months is devastating . . . The scale of suffering is heartbreaking. President Biden and I are working to end this war such that Israel is secure, the hostages are released, the suffering in Gaza ends, and the Palestinian people can realize their right to dignity, security, freedom and self-determination.”

It’s too early to say whether that was sufficient to appease a coalition that is extremely fragile if not fractured. Granted, most voters are paying less attention to policy specifics right now than trying to figure out whether Harris and Walz represent an image of America worth signing on to.

“We’ve seen so many great influencers, musical artists and actors endorse Kamala,” DeBrasco told Britain’s SkyNews, “and Trump has Kid Rock and Hulk Hogan. So who really cares about those two when you have stars that young people actually care about upfront supporting Kamala, full-throated?”

Now that the show’s over, we’re going to find out.