The Dubious Evolution of Jimmy Kimmel and Howard Stern

Is it a coincidence that both buddies have done an Extreme Makeover: Bad Boy Edition?
The Dubious Evolution of Jimmy Kimmel and Howard Stern

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Howard Stern and Jimmy Kimmel are besties.

Jimmy Kimmel Live

Stern brings best pal Kimmel a collection of his famous socks.

They travel together. They exchange pick-me-up e-mails. They even -- how adorable is this? -- pick blueberries together. And, seemingly, they have gone through Extreme Makeover: Bad Boy Edition together, leaving their scandalous pasts behind to create kinder, more sensitive versions of their showbiz selves. 

Are they seeing the same career makeover artist? Looking at each celeb’s 2010s, it sure seems that way. The similarities are stunningly obvious:

  • Connecting to huge (mostly male) audiences by joking around with nearly-nude women and tip-toeing up to the edge of racial humor? Check
  • Working to scrub the Internet of evidence of the above? Check
  • Transforming their physical appearance from schlubby to stubbled suave? Check
  • And taking the moral high ground on issues like the misogynistic treatment of women? One big ironic check.

Let’s take a look at the extreme makeover that each has undergone before asking the cynical question:  Are we really supposed to believe Stern and Kimmel are enlightened human beings now? 

Jimmy Kimmel: “We can’t let bad behavior slide anymore”

Thanks to his impassioned late-night pleas about health care and gun control, CNN has called Jimmy Kimmel “America’s conscience.”

Jimmy Kimmel? 

This is the man who, along with bro-tastic podcaster Adam Carolla, brought you the Juggies, women in skimpy bikinis who ended each episode of The Man Show by bouncing on trampolines. 

This is the man infamous for multiple appearances in blackface as NBA star Karl Malone, a series of bits for which he’s apologized. But does anyone remember that he also painted his face brown to jab Oprah?

This is the man who used to chug beers with Carolla on The Man Show, a tradition he tried to bring to Jimmy Kimmel Live! until an audience member vomited and ABC said “please no more getting sauced on the couch with George Clooney.”

It’s the disconnect between the old and new comedy personas that makes you squint to determine which is the real Kimmel. 

There’s New Jimmy, the one who hosted the 2018 Academy Awards and told the audience: “We can’t let bad behavior slide anymore. What happened with Harvey (Weinstein) and what’s happening all over was long overdue. The world is watching. We need to set an example.”

The problem is, Old Jimmy had already set an example. Back on The Man Show, a program he promoted as “a joyous celebration of chauvinism!”, he did bits like asking women on the street to guess what was in his pants.  During another segment, Old Jimmy tried to guess the weight of different women, asking them to take off their clothes so he could make a better assessment. With one woman, he didn’t bother trying: “I’m not even going to guess your weight. You know why? I’ve got an erection.”

But Old Jimmy was a problem for New Jimmy. It’s one thing to ogle half-dressed women on the number-two rated show on Comedy Central. It’s another thing when you’re the face of late night on one of the country’s major networks. (Admittedly, not as big a deal as it once was.)

When his talk show launched in the early 2000s, Kimmel notoriously had trouble booking female guests outside of Tammy Faye Baker. Perhaps, theorized one pundit, that was from women’s fear of finding themselves on an episode of The Man Show II.

Of course, New Jimmy would have to renounce this past if he was going to swim in the bigger showbiz ocean.

“I look back at every show I’ve ever done and cringe. My vision of hell is a bunch of monitors with my old shows running on them,” New Jimmy told Vulture. “We did a lot of stupid stuff.” 

Comedy Central/Jimmy Kimmel Live

From shlub-a to hubba hubba

Over the past fifteen years, Kimmel cleaned up his act -- literally.  He lost 25 pounds, transforming himself from a beer-chugging slob into a bearded charmer who’s borderline handsome. Gone are the open-necked shirts and jackets of Live!’s early days -- he’s now in fitted suits and ties that Johnny Carson would have envied. 

Fans of New Jimmy would also argue that he’s grown up.  His son’s health struggles prompted Kimmel’s fight to preserve the Affordable Care Act.  And his worry about America’s future caused him to rethink his approach to late night. 

“There’s definitely been a shift in my feeling about the country over the last year or so,” he said in 2017 as the Trump administration settled in. “I feel frustrated. I don’t know — maybe a lot of it is media hysteria, but I go to bed worried and I wake up worried, and I honestly don’t know if things are going to be okay.”

A friend insists that Kimmel has transformed from a chauvinistic joker into an empathetic conversationalist. “He really does listen. Not everybody has that ability to let someone else shine. It seems obvious, but a lot of people let their own ego get in the way.”

(The friend, in this case, is Howard Stern. 

Howard Stern: “I sound insane”

While many argue that Stern has become an amazing interviewer as well, that wasn’t always the case. 

“The old Howard was an insecure narcissist so terrified his audience would turn the dial that he bullied his guests to either submit or flee,” writes Geoff Edger in the Washington Post. “The new Howard is a kinder, happier, and more generous entertainer freed from the constraints of shock jockdom.”

There’s a lot that New Howard has left behind. When his show moved to satellite radio in 2004, Old Howard was like a kid in a topless lesbian candy store -- everything that the FCC had denied him was now fair game. If you longed for porn stars riding vibrating gizmos, humiliated members of the Wack Pack, or games like the Biggest Whore Contest, Old Howard had a show for you.


Ralph Cirella works his magic.

New Howard would like you to forget all that. He denounces his first two books, Private Parts and Miss America:  “I hate them,” he says now. ”If you read my books or listen to my old raps, I sound insane.”

“I tried to watch some of my old Letterman ,” Stern told the Washington Post. “I couldn’t get through two minutes of it. It’s just not me. I don’t know who that guy is.”

You can watch these old appearances on YouTube – but Stern won't.

You might have trouble finding those older bits on YouTube or other online outlets--someone in Sternland has been working hard to scrub the Internet of audio that New Howard regrets. It’s out there, but you’re going to have to work for it. Fans still find ways to share classic files on torrent sites, but those efforts are pretty underground. Some complain on Reddit that Stern staffers are even posing as Howard superfans to shut down bootleg file sharing. 

There’s plenty of New Howard out there, however. He claims three factors fueled his evolution:

  • His divorce from Alison Berns after 23 years of marriage sent him into a tailspin, resulting in four-days-a-week therapy sessions. Stern credits that intense psychotherapy for helping him overcome his anything-for-attention tendencies.
  • His subsequent remarriage seems to have brought a new sense of calm. “Words cannot describe the change in my attitude and spirit because of Beth,” he writes in 2019’s Howard Stern Comes Again
  • But the biggest motivator might have come from his daughters. “I’ve always wanted (my daughters) to be proud of the work I’ve done on the radio—and on myself,” he says.  In-depth interviews with America’s biggest celebrities might inspire that pride. Lesbian Dial-A-Date likely does not. 

Like Kimmel, the evolution has been good to Stern.  Guests like Ass Napkin Ed and Hank the Angry Drunken Dwarf have been replaced by the likes of Mick Jagger and Jennifer Aniston.   

“These in-depth interviews—that’s what I’m most proud of,” he says. “It’s one of the things I want to be remembered for before I die of a noncancerous cyst. I want my show to be funny, irreverent, but also touching.”  

Touching?  Old Howard would have gone off on a guy like that. 

“You could still ask your masturbation question, but with class.”

Given that the two best pals have enjoyed similar career makeovers over similar timelines, it’s no wonder some Reddit users speculate Kimmel is behind Stern’s transformation from a-hole to A-lister. 

It’s easy to imagine that the two stars have talked about it. But both claim life circumstances and a changing world are the factors behind their personal growth.  It’s certainly possible. This is what we want from our problematic celebrities, right?  Maturation? A change for the better?

But let’s be cynical for just a moment.  While both men likely are embarrassed by stupid stuff they’ve done in the past (who isn’t?), the Kimmel/Stern evolution is also likely driven by profession and profit.

Old Jimmy couldn’t book top female stars on Jimmy Kimmel Live!  If he truly tried to do Man Show II, that would still be the case. Or rather, it wouldn’t -- Jimmy Kimmel Live! would have been canceled a long time ago. While growing up was a natural thing to do, it was also critical for New Jimmy’s career. 

(For what it’s worth, New Jimmy thinks Man Show II would work just fine. “If we put The Man Show on today in its identical form, it would be an even bigger hit than it was back then,” he says. “It would absolutely result in a s---storm, and there’s absolutely nothing better for ratings than a s---storm.”)

Comedy Central

Bikinis + beer = basic cable gold

As for Stern, he has all the money he needs. But for the professional credibility he craves? On his Howard Stern Comes Again book tour, he named Jagger as his dream guest.  In 2006, there was no way Mick was going to show up for Old Howard’s questions about his pubic hair. In 2021, New Howard’s dream came true. He finally has the respect of his idols -- for a man of Stern’s admitted insecurities, that counts for a lot. 

In the end, Extreme Makeover: Bad Boy Edition is likely a mix of personal growth and professional realities. Does that make them sell-outs?

New Howard argues that he’s still irreverent and that his show continues to feature pranks and sex talk. “I try to hit all the bases,” he says. “You could still ask your masturbation question, but with class.”

That’s not enough for some Stern fans. Podcaster C.C. Webster sums up the criticism:

The show has gotten less funny because Howard turned into the mainstream celebrity that he used to ridicule; in a decade that consisted of culture wars over political correctness and conformity, he adopted PC lines rather than persist as the radical rebel he used to be; finally, he turned his back on both the fans and the spirit of the show that made him the “King of All Media.”

New Howard gets the blowback.  And he doesn’t care. “To the guy who wants me to do the same thing over and over again: Hey, I understand you,” he told Rolling Stone

“But I’m not your guy.”

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Top image: Jimmy Kimmel Live

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