Chris Redd Roasts ChatGPT’s Juneteenth Flop
Comedian takes playful jab at AI’s awkward holiday design in a viral Instagram laugh-fest!
Image: Instagram
Chris Redd, the Emmy-nominated comedian best known for his run on Saturday Night Live, used Juneteenth as an excuse to call out artificial intelligence—and the results were predictably hilarious. In a new Instagram post shared on June 19, Redd challenged ChatGPT to spin a celebratory message from one of his own photos, only to watch the bot churn out what he bluntly labeled “THIS NONSENSE!”
Ai Goes Off Script
In the two-shot Instagram carousel, Redd first shows a composed portrait of himself, followed by a second snap of a mystery man sticking out his tongue in full comedic flair. Underneath, Redd wrote: “I asked ChatGPT to use the second pic to make an uplifting, fun post about Juneteenth and it shit out THIS NONSENSE! 😂😂😂😂😂😂 ‘STILL FEELING FREE’ ?!! Also, WHO IS THIS MAN?! Why is his tongue out like that?! I don’t know about AI but my ChatGPT isn’t taking anybodies job any time soon 🤦🏾♂️”
Rather than a polished homage, the chatbot’s response reportedly slapped the images together with the baffling tagline “STILL FEELING FREE,” completely missing the mark on cultural resonance. Redd’s reaction—side-eye emoji included—quickly racked up more than 400,000 likes as fans chimed in with laughter and memes of their own.
Satire Meets Social Media
The comedian’s post tapped into a larger conversation about the limits of AI in creative spaces. While bots can analyze data and replicate styles, they often struggle to capture nuance—especially when it comes to historically significant moments like Juneteenth. Redd’s followers flooded the comments, with one fan writing, “The AI is cute but it ain’t no comedian,” and another joking, “Even ChatGPT can’t touch your timing, Chris.”
AI-generated art and copy have become increasingly common on social feeds, but Redd’s playful takedown underscores that human context still reigns supreme. By spotlighting the bot’s misfire, he reminded fans that authentic humor and cultural literacy aren’t easily automated.
Beyond The Bot
This isn’t Redd’s first time merging technology and comedy. The 38-year-old broke out in digital sketches before joining SNL’s cast in 2017, where he earned acclaim for spot-on musical impressions and original characters. After leaving the show in 2022, he continued to appear in films like Popstar: Never Stop Never Stopping and the Prime Video series 1 Happy Family USA.
Born Christopher Jerell Redd in St. Louis, he studied at Illinois State University before breaking into stand-up. Alongside awards nods and red-carpet moments, Redd has often used social platforms to test material and engage directly with fans—whether riffing on current events or roasting his own AI experiments.
On Tour And On Point
Redd’s comedic momentum extends well beyond Instagram. In a related post from early June, he announced new stand-up dates across the country, kicking off this month in Manchester, Connecticut, followed by stops in Tampa, Orlando and Jacksonville. His blend of observational humor and improvisation has sold out clubs from coast to coast.
Fans looking to catch Redd live can tap the links in his bio, where he’s scheduled to perform at the Funny Bone comedy chain through October. Given the buzz around his AI-skewering post, these sets may feature even more tech-inspired material.
His ability to turn a simple chatbot fail into a viral moment highlights why Redd remains one of today’s sharpest comedic voices. By twisting a Juneteenth assignment into a masterclass on timing and authenticity, he reminded us that even the smartest machines can’t replicate true human wit.
As AI continues to creep into every corner of entertainment, Chris Redd’s Instagram roast stands as a reminder: when it comes to comedy, there’s no substitute for genuine perspective—and a well-placed eye roll.
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