Don Cheadle Day 2025 is here—the 6th annual celebration of photoshopping Don Cheadle into absurd scenarios delivers the best memes yet.
November 29 marks Don Cheadle’s birthday, but in internet culture, it’s become something much bigger: the annual Don Cheadle Day 2025 celebration. What started as a quirky tradition in 2020 has exploded into one of X’s most beloved recurring events, with thousands photoshopping the same image of Cheadle into increasingly absurd scenarios. Organized by YouTuber Schaffrillas, the 6th annual Don Cheadle Day kicked off with the call to “photoshop this photo of Don Cheadle into wacky scenarios” using #DonCheadleDay—and the internet delivered in spectacular fashion.
As of November 29, 2025, #DonCheadleDay is dominating global trends, with creative, unhinged, and genuinely hilarious edits flooding timelines. From movie poster parodies to anime crossovers, this year’s batch might be the strongest yet. Whether you’re a longtime Cheadlehead or just discovering the chaos, these memes perfectly capture why Don Cheadle Day remains an internet holiday worth celebrating.
The Origin of Don Cheadle Day: How It All Began
Don Cheadle Day traces back to Schaffrillas (James Phyrillas), the popular film YouTuber known for ranking animated movies. In 2020, he declared November 29 “Don Cheadle Day” and started the photoshop tradition with one specific image of Cheadle smiling in a grey shirt.
The rules are simple but brilliant: take that exact photo and put Don Cheadle anywhere ridiculous. No context, no explanation—just pure surreal humor. What began as a small bit has grown into an annual event with thousands of participants, including celebrities and artists jumping in.
As of 2025, it’s officially the 6th year, and Schaffrillas still personally retweets favorites. The tradition has evolved into a celebration of creativity, absurdity, and appreciation for one of Hollywood’s most versatile actors.
Why Don Cheadle Day 2025 Is Bigger Than Ever
This year’s celebration feels particularly massive. With X’s algorithm favoring visual content and meme culture stronger than ever in 2025, Don Cheadle Day hit trending within hours of Schaffrillas’ announcement.
The beauty lies in its purity: no sponsorships, no cash prizes—just people having fun photoshopping Don Cheadle into increasingly deranged situations. From Kaiju battles to Mario Kart rosters, the creativity on display shows why this remains one of the internet’s healthiest recurring memes.
Even Don Cheadle himself has acknowledged the phenomenon in past interviews, calling it “weird but flattering.” In 2025, with meme culture more sophisticated than ever thanks to AI tools and better editing apps, the quality of submissions has reached new heights.
The Best Don Cheadle Day 2025 Memes So Far
Here are some of the absolute standout entries that are making the rounds:
This masterpiece reimagines Don Cheadle in a massive Kaiju arc, complete with dramatic anime styling that’s genuinely impressive. #DonCheadleDay
#DonCheadleDay https://t.co/UptJCAh9iA pic.twitter.com/9q0U49zvhD
— CodeDusq (@CodeDusq) November 29, 2025
A perfect Back to the Future parody with the timeless line: “We’re going back in time to the first Thanksgiving to get Don Cheadle off the menu.” Pure gold.
Took me a while to make this, but I’m glad I did.#DonCheadleDay pic.twitter.com/5RFsXViJF1
— Moltended (@Moltended) November 29, 2025
Mario Kart fans rejoice—someone finally created the ultimate Cheadle Kart roster, complete with custom karts and power-ups. The attention to detail is chef’s kiss.
“Two Cheadle Trucks, Making Dons” – LeDon DeDon #DonCheadleDay https://t.co/IWFzMqzCZe pic.twitter.com/0OcDKMAwk6
— Sanchewich (@Sanchewich) November 29, 2025
“Two Cheadle Trucks, Making Dons” takes a classic meme format and elevates it to art. The delivery trucks full of Cheadles is sending people.
IT’S CHEADLE KART TIME!!! #DonCheadleDay https://t.co/ks9j7bumeV pic.twitter.com/alE5hQY6pN
— Jkop (Sylux) (@BubblesZap_) November 29, 2025
One of the most elaborate entries: a full cast replacement with nothing but Don Cheadle faces in various expressions. The commitment deserves an Oscar.
We’re going back in time to the first Thanksgiving to get Don Cheadle off the menu.#DonCheadleDay pic.twitter.com/6KEf4I1RoY
— ♡ chelsea rose ♡ (@_toastedsea_) November 29, 2025
This cinematic beauty parodies a famous horror poster with multiple floating Cheadle heads—truly the stuff of nightmares (the good kind).
HAPPY DON CHEADLE DAY!!!! I PRESENT, DON DO DON KAIJU ARC!! #DonCheadleDay https://t.co/05usPnMBkW pic.twitter.com/Lbjird4yug
— 🦉🦉The Bonafide Genuine Lynneshade🦉🦉 (@Lynneshade41) November 29, 2025
Conclusion: Happy Cheadling Everyone!
Don Cheadle Day 2025 proves once again why the internet is beautiful: thousands of strangers uniting to photoshop one man’s face into absurd scenarios for no reason other than joy. In a world of divisive trends, this remains pure, wholesome chaos.
The best part? It’s not over yet—Don Cheadle Day runs all day November 29. Grab that template photo and make your own masterpiece. Who knows, Schaffrillas might retweet yours.
What’s your favorite Don Cheadle Day meme this year? Or are you making one right now? Drop it below—let’s keep the Cheadleing going!