8 hilarious moments from Chicago DNC: From Obama’s ‘crowd size’ joke to Bill Clinton’s age swipe at Trump

8 funny moments that left DNC crowd in splits including Oprah Winfrey's 'cat lady' zinger

While the 2024 Democratic National Convention did feature a healthy portion of serious political dialogue, it also had moments that left everyone in splits. With speeches that were not only powerful but also sprinkled with humor, one could say the convention offered a much-needed respite from the otherwise brutal politicking that only intensifies in the months leading up to Election Day. The convention wrapped up its four-day run as Vice President Kamala Harris accepted the party’s nomination for president—leaving us with plenty of memorable moments. Let’s take a look back at some of the funniest highlights from the event.

1. Michelle Obama’s clever dig at Trump

Michelle Obama didn’t hold back when it came to poking fun at Donald Trump during her speech. She zeroed in on a comment Trump made about migrants taking "Black jobs" as part of his outreach to Black voters. With her trademark wit, she quipped, "I want to know who's going to tell him that the job he's currently seeking might just be one of those Black jobs."

2. Barack Obama’s crowd size joke

Barack Obama brought his usual charm and humor to the convention, especially when he took a jab at Trump’s obsession with crowd sizes. During his speech, Obama mimicked Trump by moving his hands closer together and farther apart, a nod to Marco Rubio’s famous "small hands" comment during the 2016 Republican primary. Obama joked, "There's the childish nicknames, the crazy conspiracy theories. This weird obsession with crowd sizes," leaving the audience in splits.

3. Hillary Clinton loving the 'lock him up' chants

Hillary Clinton made a powerful return to the DNC stage, where she couldn’t resist poking fun at her former opponent's legal troubles. As she spoke about Trump’s courtroom antics, she noted, "Donald Trump fell asleep at his own trial, and when he woke up, he made his own kind of history, the first person to run for president with 34 felony convictions!" The crowd responded by chanting "Lock him up." Clinton smiled and nodded, letting the moment speak for itself.

4. Doug Emhoff’s hilarious voicemail story

Kamala Harris's husband Doug Emhoff shared a heartwarming yet humorous anecdote during his DNC speech. He talked about leaving a long, rambling voicemail after his first phone call with Harris—a message she still plays for him every year on their anniversary. Emhoff recalled, "I got Kamala's voicemail and I just started rambling. 'Hey, it's Doug. I'm on my way to an early meeting. Again, it's Doug,'" which had the audience laughing.

5. Kenan Thompson’s take on Project 2025

Comedian Kenan Thompson injected some much-needed humor into the convention on the third night, delivering a performance that felt like a live skit straight out of 'Saturday Night Live'. Thompson joked about Project 2025—a Republican plan for Trump’s potential second term—holding up a thick, bound version of the document. He quipped, "You ever seen a document that could kill a small animal and democracy at the same time?"

6. Tim Walz’s football-themed pep talk

Minnesota Governor Tim Walz took the stage with the same energy as that of a coach giving a pep talk. He didn’t just focus on politics; he emphasized the importance of personal freedoms with a straightforward line: "Mind your own damn business." Walz concluded his speech with an encouraging sports metaphor: "It is the fourth quarter, we are down a field goal, but we are on offense and we've got the ball."

7. Bill Clinton’s age joke

Former president Bill Clinton also added some humor to the convention with a playful jab at Trump’s age. Reflecting on his own age, Clinton said, "Two days ago, I turned 78. The oldest man in my family who is still living. And the only personal vanity I want to assert is that I'm still younger than Donald Trump," which drew cheers from the crowd.

8. Oprah’s 'cat lady' joke

Oprah Winfrey’s appearance at the convention was a big moment, and she didn’t disappoint. Known for her warmth and storytelling, Oprah gave a speech that resonated deeply with the Democrat audience, Newsweek reported. But it was her humor that stood out, especially when she quipped, "When a house is on fire, we don’t ask whose house it is. If the place happens to belong to a childless cat lady, well, we try to get that cat out too."