Jimmy Kimmel and Sean Hannity’s most embarrassing career moments

Sean Hannity dredged up some embarrassing — and controversial — moments from Jimmy Kimmel’s past as ammunition in their ongoing war, but there are even more embarrassing career missteps tracing back to the both of them.

The feud between the TV personalities began earlier this week after Kimmel made jokes about Melania Trump during his monologue, which angered Hannity and led him to call Kimmel a “disgrace” and an “a– clown.”

But it didn’t just end there.

Kimmel woke up Thursday to learn Hannity had been talking smack about him and he fired right back.

The back-and-forth insult parade escalated on Friday when Hannity took to Twitter to unearth old videos of the late-night TV host on his past Comedy Central series “The Man Show” — and called him names like “pervert” and “Harvey Weinstein Jr.”

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Jimmy Kimmel and Adam Carolla on “The Man Show” in 1999.

(AF archive / Alamy Stock Photo/Alamy Stock Photo)

Hannity slammed Kimmel as a pervert and a racist in his Twitter posts and radio show commentary on Friday — particularly drawing attention to two “Man Show” segments, one where Kimmel wore blackface to impersonate NBA star Karl Malone and another where he asks a young woman to feel the front of his pants and guess what’s inside.

On Saturday, Hannity said he won’t be backing down from his attacks on Kimmel until the comedian apologizes for making fun of the First Lady’s accent.

Kimmel, an outspoken detractor of President Trump and Hannity, a conservative pundit who defends the President, both have had even more questionable moments lining their pasts.

Sean Hannity interviews President Donald Trump on "Hannity" on October 11, 2017.

Sean Hannity interviews President Donald Trump on “Hannity” on October 11, 2017.

(Fox News)

Here’s a look at some of them:


Despite Hannity calling Kimmel a racist for his reoccurring Karl Malone segment, the Fox News host has come under fire for his involvement in birtherism where he demanded former President Barack Obama produce his birth certificate and prove he was born in the United States.

Hannity gave Trump a platform in 2011 to spew his ideas on Obama’s origins on his show, prior to the billionaire’s run for the presidency, and it was there that Trump said Obama could have “easily come from Kenya or someplace.”

In 2016, Hannity brought attention to it all again when he offered to buy Obama a “one-way ticket to Kenya.”

In 2015, Hannity called for a ban of rap music when stores decided to ban the Confederate flag.

He compared the use of the “n-word” on the tracks and “racist, misogynist” slurs in hip-hop songs to selling the Confederate flag — which is its own symbol of racism, slavery and white sumpremacy.

On “The Man Show,” which aired from 1999 to 2004 and described itself as “a joyous celebration of chauvinism,” Kimmel did portray Malone several times while completely covered in brown makeup, yet defended himself against Hannity’s criticism by declaring he and Malone are on good terms.

“As a matter of fact, Karl @TheDeliverer_32 is a man I love dearly and this photo hangs in our office,” Kimmel tweeted, along with a photo of him and Malone “Thanks for the shout-out!”

A number of other racist and homophobic jokes were thrown around in the series, for example in the sketch of the “The Man Show Boy” when the 11-year-old says he can’t believe his dad left him with “gay Asian dudes” and responds that he doesn’t ask to see the green cards for two bodega clerks when they ID him.


The term “racist a–hole” may have been used to take a dig at Kimmel, but truly his most cringe-worthy moments all stem from sexualized bits on “The Man Show.”

Nearly the entire premise of “The Man Show” was to ogle women — there was a segment solely dedicated to women jumping on trampolines and a team of models called “Juggies” who were there just to be looked at, it seemed.

Hannity did shine light on one uncomfortable “Man Show” skit where Kimmel asks a young woman to guess what’s inside his pants and then makes an off-color comment that it might be easier if she used her mouth.

This, however, was just one of the bizarrely inappropriate things he had done on the show along with co-star and co-creator Adam Carolla.

In the very first episode, the two bros stand atop the Hoover Dam and proclaim they are building a dam: “a dam to hold back the title wave of feminization that is taking over this country; a dam to stop the estrogen that is drowning us in political correctness. A dam to urinate off of when we’re really drunk. We call this dam: The Man Show.”

This leads into them slamming countless women on TV, including Oprah, and offering what they think men really want to see: “girls jumping on trampolines, monkeys, and midgets.”

Another segment featured an 11-year-old boy, called the Man Show Boy, where he would approach older women and make sexual jokes and proposals to them and tried to purchase porn. Carolla and Kimmel also held a “Juggy Talent Show” where they paraded women in swimsuits with random talents and made sexual jokes in response.

After one “Juggy” reveals he can “eat an entire banana in one bite,” Kimmel whispers something into Carolla’s ear, who responds into the mic: “That’s right, it could be a penis!”

There were also several more segments that could be dissected such as “wife school” and a segment where Kimmel guessed women’s weight.

To one of the woman, he says, “You know what? I’m not even going to guess your weight. Why? Because I’ve got an erection!”

In an interview with New York Magazine in Oct. 2017, Kimmel reminisced about “The Man Show” and said: “I look back at every show I’ve ever done and cringe.”

“We always said The Man Show’s audience was divided between people who thought it was funny and understood we were joking and other people who really thought we had some kind of an agenda,” he explained, not regretting it, but admitted they did a lot of stupid stuff.

He also explained that if it were on today it would be a bigger hit because “there’s more back to lash against.”

“There’s more scrutiny. There’s more political correctness. That always offers more opportunity to run counter,” Kimmel continued.

Hannity showed himself a sexist when trying to defend President Trump’s “grab them by the p—y” hot mic video. The political pundit found an interesting source of inspiration to defend Trump: the bible.

“King David had 500 concubines for crying out loud,” he said during a discussion about the disparaging remarks.

Later in the October 2016 segment, Hannity did admit the comments were misogynistic, but quickly changed gears to focus on Bill Clinton’s scandal with Monica Lewinsky.

Seth Rich, a 27-year-old data analyst at the DNC, was shot and killed early one Sunday morning last month in what police say was robbery gone wrong. He was killed while walking home in a Washington, D.C. neighborhood that has seen a recent uptick in crime.

Seth Rich, a 27-year-old data analyst at the DNC, was shot and killed early one Sunday morning last month in what police say was robbery gone wrong. He was killed while walking home in a Washington, D.C. neighborhood that has seen a recent uptick in crime.


Conspiracy theory

One of Hannity’s most recent controversies is the conspiracy he began pedaling that DNC staffer Seth Rich’s killing was actually coordinated by Hillary Clinton and her team. Several advertisers pulled out of Hannity’s show because of his coverage and the conservative magazine, National Review, called it a “disgrace.”

After speculation that Rich was in contact with WikiLeaks before his death, Hannity promised to “look into” the death, which he called “suspicious.”

Rich, 27, was shot and killed outside of his home in D.C. in July 2016. His family sued Fox News in March for pedaling the conspiracy theory.

Kimmel found himself an almost-political pundit in the Trump era after making an impassioned plea about health care after his newborn son Billy had to undergo heart surgeries and then again to attack Trump and Congress about gun control in the wake of the Parkland, Fla., shooting.

The company you keep

  • Hannity loves Trump. Kimmel loves Affleck.

The feuding duo has some friends in low places.

Kimmel was criticized in the wake of #MeToo for his relationships with Matt Damon and Ben Affleck, who were under fire for their reactions to the mounting accusations against their friend and business partner, Harvey Weinstein.

Jimmy Kimmel and Ben Affleck appear in a 2009 video from the "Jimmy Kimmel Live Show."

Jimmy Kimmel and Ben Affleck appear in a 2009 video from the “Jimmy Kimmel Live Show.”

(Jimmy Kimmel Live)

Affleck faced some sexual harassment allegations of his own amid #MeToo.

His years long joke of bumping Damon from his show resulted in a music video featuring Kimmel’s then-girlfriend Sarah Silverman singing about “f–king Matt Damon.” As retribution, Kimmel made a music video with Damon’s dear friend Affleck, where he sings about “f–king Ben Affleck” along with several star-studded cameos.

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