Best Moments on Jimmy Kimmel Live! — Highlights You Can’t Miss

Jimmy Kimmel Live! has long blended sharp satire, bold commentary, celebrity interactions, and emotional honesty. Over its run, the show has delivered unforgettable moments that resonate beyond late-night television. Here are some of the most striking ones — and why they matter.

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1. The Comeback Monologue: Breaking YouTube Records

After a suspension by ABC in September 2025 (following controversial remarks about the killing of activist Charlie Kirk), Jimmy Kimmel Live! returned with a powerful opening monologue. Rather than dodge the issue, Kimmel addressed it head-on, speaking about free speech, the backlash he faced, and the importance of his platform.

• That comeback monologue became his most-viewed YouTube segment ever, amassing over 15 million views in just 16 hours. Гардиан
• The broadcast also drew 6.26 million viewers, one of the show’s highest ratings in years. Гардиан

This moment crystallized how late-night hosts are not just entertainers, but also voices in cultural debate.

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2. Taunting Trump Over a Poll

In October 2025, Kimmel used his monologue to highlight that a recent YouGov poll gave him a 16-point lead over former President Donald Trump in net favorability. He leaned into comedic jabs — mocking Trump for lacking scandals and suggesting that even an odd item like “a toenail in a salad” might be more popular. EW.com+1

What’s especially memorable: Kimmel turned what could’ve been a dry data point into a hilarious, pointed performance in real time.

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3. Politically Charged Commentary on Trump’s National Guard Moves

When Trump moved to deploy the National Guard in Democrat-run cities, Kimmel didn’t stay neutral. He lambasted the decision as “incredibly dangerous and unnecessary,” and framed it as theatrical political posturing rather than genuine crisis response. Гардиан

Late-night hosts are increasingly expected to respond to current events. Kimmel’s willingness to wade into these debates is part of what makes his show culturally relevant.

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4. Roasting Adrien Brody’s Long Oscars Speech

During the 2025 Oscars, Adrien Brody gave an exceptionally long acceptance speech — even dismissing the orchestra’s attempt to “play him off.” Kimmel roasted this in a hilarious segment: “Who knew you could stop the band from playing you off?” He also quipped that the long speech gave enough time for other events, weaving absurdity and wit. decider.com

This moment shows Kimmel’s joy for blending pop-culture commentary with playful humor.

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5. Alan Cumming’s Monologue on Trans & Immigrant Rights

In July 2025, guest host Alan Cumming used his opening monologue to deliver a sharp, satirical call for trans and immigrant rights. He wove political critique with humor, addressing health-care cuts, state violence, and marginalized communities in a way that felt earnest and unflinching. Them

This demonstrates how Kimmel’s platform allows for serious cultural and social issues to surface in late-night TV.

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6. Becoming a Grandfather Live On Air

In May 2025, Kimmel made a deeply personal announcement: he had become a grandfather. He missed only his second show in 22 years to be with family, then returned to monologue with emotion, joking about baby names and reflecting on the world his granddaughter would inherit. EW.com

Moments like this expose the human side of hosts behind the jokes.

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7. Roasting Hollywood in Style

Kimmel has never shied from skewering celebrity absurdities. A standout: in 2025 he took aim at Adrien Brody again after the Oscars, mocking how Brody refused to be ushered off stage even when the band cut in. decider.com

Such bits remind audiences he’s both in the industry and willing to lampoon it without mercy.

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8. The Damon–Kimmel Feud & On-Air Gags

Beyond monologues, Kimmel’s feud with actor Matt Damon (and jabs at Ben Affleck) has become part of late-night lore. In 2023, he pretended to freeze a FaceTime call with Damon during a promo, repeatedly showing unflattering views and deriding the actor’s film work. Википедия

These playful rivalries keep the show lively and unpredictable.

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Why These Moments Stick

• Emotional honesty: Kimmel’s real grief, defense of free speech, and family stories resonate.
• Topical engagement: He doesn’t shy away from current events — he leans in.
• Comedic sharpness: He combines wit, absurdity, and satire in a swift package.
• Cultural awareness: Whether celebrity roasts or social issues, he knows which moments land.