If you had "Jack Black and Kathy Griffin dated" on your Hollywood bingo card, you’re either a superfan or lying. Honestly, most people didn't know this was even a thing until Griffin started dropping truth bombs on TikTok recently.
It’s one of those weird, 1990s pairings that makes total sense once you hear it, yet feels completely surreal. Back then, Jack Black wasn’t the guy from Kung Fu Panda or the beloved internet "dad" of Tenacious D. He was just a guy with a messy apartment on Vermont Avenue in Los Angeles. Kathy Griffin, meanwhile, was hustling in the stand-up scene, years away from the Emmy wins and the massive political firestorms that would eventually define her career.
What’s wild is how their names have stayed linked, not just because of a brief romance, but because they’ve both ended up as poster children for how fast Hollywood can turn on you when a joke goes sideways.
The Vermont Avenue Days: Towels and "Bros"
Let’s get the juicy stuff out of the way. In early 2025, Kathy Griffin posted a video on social media that basically broke the celebrity-lore corner of the internet. She shared a photo of them looking cozy on a couch—Jack with a full head of hair, both looking like the quintessential '90s alt-scene couple.
Griffin joked that "dating" was a very loose term for what they had. Basically, they hooked up a handful of times. But she had this one specific memory that perfectly captures the Jack Black vibe before he was famous. She recounted staying the night at his place and asking for a towel after her shower.
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His response? "You’re standing on it."
He was using the bath mat as a towel. It’s gross. It’s hilarious. It is exactly what you’d expect from a guy who would later write a song called "Double Team." Griffin laughed it off, saying she kept sleeping with him anyway because, well, it was Jack Black. Interestingly, she also noted he was the first guy she ever dated who made her feel "cool" to other men. Apparently, the "bros" in the comedy scene respected Jack so much that dating him gave her a weird kind of status.
When the Jokes Stopped Being Funny
While the towel story is a fun piece of trivia, the real connection between Jack Black and Kathy Griffin is much heavier. It’s about the "line." Both performers have famously crossed it, and both faced massive, career-altering blowback for it.
For Griffin, it was the 2017 photo. You know the one—the Trump mask and the ketchup. It was meant as a commentary on a specific sexist comment Trump had made about Megyn Kelly, but the nuance was lost in the gore. She lost her CNN gig, ended up on the no-fly list, and was investigated by the Secret Service. It took her years to crawl back into the mainstream.
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Then, in 2024, it was Jack Black’s turn.
During a Tenacious D show in Sydney, Australia, his bandmate Kyle Gass made a birthday wish: "Don't miss Trump next time," referring to the assassination attempt that had happened just 24 hours earlier. The room went silent. Then the internet exploded.
The Fallout Nobody Saw Coming
The way Jack Black handled his controversy was the polar opposite of how Griffin handled hers. Griffin doubled down for a long time, claiming her right to satire. Black, however, went into immediate damage control. He canceled the rest of the tour. He put Tenacious D on "indefinite hold." He basically threw his best friend of 30 years, Kyle Gass, under the tour bus to save his own brand.
Some fans felt betrayed. They saw Black as a sellout who abandoned his "D" brother to keep his lucrative movie deals with Disney and Universal. Others saw it as a necessary move to distance himself from political violence.
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By late 2025 and into 2026, the dust finally started to settle. Black started hinting that "we’ll be back," and reports even surfaced—though unconfirmed by his camp—that he was feeling immense pressure from Hollywood heavyweights like George Clooney to shut things down immediately after the incident.
Why Their Parallel Matters
- The Comedy Gap: Both found out that what works in a dark comedy club or a rock concert doesn't always work in a viral 10-second clip.
- The Gender Double Standard: Fans often point out that Jack Black’s "cancellation" lasted about fifteen minutes before he was back at movie premieres, while Griffin was essentially blacklisted for years.
- The Evolution of "Edgy": In the '90s, these two were the outsiders. Now, they are the establishment, and the establishment has a lot more to lose.
How to Navigate the "Cancel" Era
If there is any takeaway from the sagas of Jack Black and Kathy Griffin, it’s that the internet has a very long memory but a very short fuse. If you're a creator or just someone with a public platform, these two serve as a masterclass in risk management.
Acknowledge the room. Griffin’s mistake was thinking a high-fashion, high-gore photo would be interpreted with the same nuance as a stand-up set. Black’s mistake—or rather Gass's—was timing. Joking about a tragedy while the blood is still wet is rarely a winning move.
Consistency is key. Black’s quick pivot saved his career but dinged his "rebel" reputation. Griffin kept her reputation as a rebel but lost her income. You have to decide which one matters more to you before the crisis hits.
If you’re looking to dive deeper into the history of '90s alt-comedy, start by looking into the "The Ben Stiller Show" or the early days of the Groundlings. That’s where the DNA of these two performers really lives. Don't just follow the headlines; look at the work that made them famous in the first place—bath mats and all.