Every family has that one relative who turns every room awkwardly silent. For the Trumps, that role has been cast, recast, and permanently type-locked as Donald Trump Jr. And for seven relentless years, Jimmy Kimmel has turned Don Jr.’s chaos into late-night ammunition—methodically shredding his image, his talking points, and whatever political future he thought he had. 
What started as a petty Twitter jab has grown into one of the most brutal and consistent public humiliations in modern political pop culture. Back in 2017, Trump Sr. ranted that late-night hosts were “unfunny” and “anti-Trump.” Kimmel shot back with a savage offer: Trump could quit the presidency and take over the show. Don Jr., doom-scrolling as usual, tried to pounce—tweeting at Kimmel about Harvey Weinstein, clearly hoping to trap him in “liberal hypocrisy.”
It backfired instantly. Kimmel replied using Trump’s own “failing New York Times” language, then privately sent Don Jr. the infamous Access Hollywood tape with a chilling, quiet message: “Great. In the meantime, enjoy this.” One move, and Don Jr. was forced to remember his father’s own words about grabbing women—while trying to posture as the moral police.
From there, the feud turned into a long-running demolition project. As Don Jr. popped up across right-wing media, ranting about Hunter Biden, inflation, gas prices, and “woke mobs,” Kimmel treated him like a recurring character in a dark political sitcom: the sweaty, overcaffeinated nepo baby who wants power but can’t stop embarrassing himself.
When Don Jr. delivered that now-infamous Republican Convention speech—eyes bloodshot, voice manic, gestures jerky—“cocaine” trended higher than his father’s name. Kimmel and other late-night hosts didn’t have to say much; a slow zoom on his face said everything. Don Jr. later blamed “the lighting,” which only made the mockery worse. 
The internet nicknamed him “Cocaine Bear Jr.” long before he ever blurted out at a conference, “Luckily, I don’t snort cocaine. It’s not my thing.” That bizarre, defensive overshare became instant meme fuel. Kimmel’s style here is key: he doesn’t outright accuse—he just replays the clips, makes a sly joke about “fun dip or Sensodyne,” and lets viewers connect the dots.
Kimmel has also targeted Don Jr.’s fake tough-guy, blue-collar cosplay. He mocked his outrage over Cracker Barrel, roasted him as a “cosplay grits gobbler New York prep school nepo baby,” and joked that Don Jr. seems to think being “loud and triggered on camera” is an actual job description. Every segment chips away at the myth that he’s some rugged outsider. Instead, he’s portrayed as a pampered prep-school kid LARPing as a culture warrior.
Then came the political humiliation. Reports floated that Don Jr. was pushing hard behind the scenes for VP picks like JD Vance—choices that aged disastrously. Kimmel’s verdict? If Trump loses, he might sue to strip the “Jr.” off his son’s name. One line. Total character assassination.
Whenever Don Jr. tries to punch up—mocking Ukraine’s Zelenskyy, whining about Hunter Biden, or blaming “the deep state” for every Trump loss—Kimmel snaps back with precision: reminding viewers this is a man who lives on his father’s phone plan, whose primary skill seems to be screaming into a camera from a rustic-chic lodge while wearing $5,000 vests.
And that’s the big picture. This isn’t just random roasting. Over years and years of monologues, clips, slow-motion replays, and perfectly calibrated punchlines, Jimmy Kimmel has built a devastating narrative: Donald Trump Jr. isn’t a serious political figure. He’s a case study in privilege, insecurity, and performative outrage—desperately trying to impress a father who publicly overshadows and privately diminishes him.
In the end, Kimmel hasn’t just made Don Jr. a joke. He’s turned him into evidence—proof of how hollow, fragile, and absurd the Trump brand looks when you strip away the gold plating and just let the cameras roll.
