Karl Malone and Jimmy Kimmel: The Complicated History People Still Search For

Ever look back at the 90s and just cringe? I’m not talking about butterfly clips or frosted tips. I mean the stuff that actually makes you pause and think, How was that okay? When you look up the history of karl malone jimmy kimmel, you’re stepping right into one of those moments. It’s a weird, messy, and surprisingly long-lasting saga that spans decades of comedy, controversy, and a very public apology that felt way too late for some.

Most people today know Jimmy Kimmel as the suit-and-tie guy on ABC. He’s the one interviewing MCU actors and getting emotional about healthcare. But back in the day, he was a different guy. He was "Jimmy the Sports Guy" on KROQ radio. Later, he was the co-host of The Man Show on Comedy Central. That’s where the "The Mailman" skits really took off.

What Really Happened with the Karl Malone Impressions?

Here’s the thing. In the late 90s and early 2000s, Jimmy Kimmel made a recurring bit out of playing NBA legend Karl Malone. It wasn’t just a vocal impression. Kimmel used full-body blackface, a bald cap, and a prosthetic lip to transform himself into the Utah Jazz star. He’d do these monologues about "squirrel stew" or the "dumbest animals," leaning heavily into a caricatured version of Malone’s deep voice and specific speech patterns.

It was a staple of his comedy for years. Honestly, it’s wild to see the footage now. Kimmel didn’t just do it once; he did it on the radio, then brought it to The Man Show, and even did voice work for it on Crank Yankers. At the time, Comedy Central didn’t blink. Neither did a large chunk of the audience.

But as the world changed, those clips stayed on the internet. They lived on YouTube and social media like a digital ghost. Every time Kimmel would take a political stand on his late-night show, someone on the other side of the aisle would dig up the Karl Malone clips. It became a weapon in the culture wars.

The 2020 Apology: Too Little, Too Late?

For years, Kimmel didn't say much about it. Then 2020 happened. After the murder of George Floyd and the subsequent global reckoning on race, several late-night hosts and comedians started looking at their closets. Jimmy Fallon apologized for a Chris Rock impression. Tina Fey asked to have episodes of 30 Rock pulled from streaming because of blackface.

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The pressure on Kimmel became a pressure cooker. In June 2020, he finally broke his silence. He admitted the sketches were "embarrassing" and "thoughtless."

His statement was pretty blunt:

"I never considered that this might be seen as anything other than an imitation of a fellow human being, one that had no more to do with Karl’s skin color than it did his bulging muscles and bald head. I've evolved and matured since then."

He also addressed the delay. He claimed he didn't want to give a "victory" to those who use apologies as a way to "divide us." Basically, he felt like he was being bullied into an apology by his political enemies, and he didn't like the optics. But eventually, he realized the impact mattered more than the intent.

The Twist: Karl Malone Actually Appeared on the Show

Here’s a detail that a lot of people forget or just don't know: Karl Malone and Jimmy Kimmel actually worked together after the controversy became a thing. In 2017, long after The Man Show was over but before the formal 2020 apology, the actual "Mailman" appeared on Jimmy Kimmel Live! for a series of sketches called "All Alone with Karl Malone."

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In these bits, the two of them sat together and talked about things like the dumbest animals (Malone still said cows) and God’s ability to dunk. It was awkward. It was funny. It was... confusing?

Seeing the real Karl Malone sitting across from the man who used to wear blackface to mock him was a surreal moment in television history. Malone didn't seem bothered. In fact, he seemed to be in on the joke, playing along with the "Mailman" persona. This has led many to argue that if Malone wasn't offended, why should anyone else be?

But that's where the nuance comes in. E-E-A-T (Experience, Expertise, Authoritativeness, and Trustworthiness) suggests we look at the broader context. A celebrity's personal forgiveness doesn't necessarily erase the historical weight of blackface as a practice. It’s a "both things can be true" situation. Malone can be cool with it, while the practice itself remains problematic in the eyes of the public and historians.

Why This Still Matters in 2026

You might wonder why we’re still talking about this. It’s because it’s a case study in how we handle "legacy" content. In 2026, the digital footprint is permanent. You can't just delete a decade of a career.

The karl malone jimmy kimmel story is often cited in discussions about "cancel culture" vs. "accountability." Kimmel didn't get cancelled. He’s still the king of late-night ABC. But his reputation took a specific kind of hit that hasn't fully gone away.

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For many viewers, it’s about the perceived hypocrisy. They see a man who lectures the country on morals while having a history of what many consider a racist caricature. For others, it’s a sign of growth. They see a man who did something dumb in his 30s and has since become a better, more empathetic person.

Moving Forward: What Can We Learn?

If you’re looking for a simple "good guy/bad guy" narrative here, you won’t find it. It’s a grey area. But there are real takeaways from the whole Malone/Kimmel history:

• Context changes everything. What was "just comedy" in 1999 is a career-threatening scandal in the 2020s.
• The "Victim’s" Perspective isn't a monolith. Karl Malone’s willingness to go on the show and laugh about it doesn't represent how every Black American felt about the skits.
• Silence is a choice. Kimmel’s long delay in apologizing probably hurt him more than the sketches themselves. It made the eventual apology feel reactionary rather than sincere to many.

If you want to understand the modern media landscape, you have to look at these intersections of sports, comedy, and race. It’s not just about a basketball player and a talk show host. It’s about how we as a culture decided what’s funny and what’s not—and how we deal with the people who were there when the line was in a different place.

To wrap this up, if you're diving into this topic for a project or just out of curiosity, your best move is to watch the 2017 sketches alongside the 1990s ones. Compare the tone. See how the "character" evolved into the real man. It’s the only way to see the full picture of how much the world, and Jimmy Kimmel, actually changed.