Howard Stern may be an evolved man nowadays, but the legendary radio host was once known for constantly pushing buttons. This usually meant that he was offending somebody with one of his gags or simply by sharing his opinions.

But Howard managed to run afoul of one of his favorite celebrities... Hugh Hefner. And he did this by entertaining one of his playmates... one who also happened to be his ex-fiance...

When Crystal Harris Went On The Howard Stern Show Things Got Crazy

The Playboy Mansion and all things Playboy have always been a notable component on The Howard Stern Show... at least throughout the '80s and '90s before Howard's personal and creative evolution which turned a lot of his old fanbase against him but opened up the door to a wider audience. While Hugh Hefner has appeared on The Howard Stern Show once or twice, he was extremely relevant to the show... but not always for reasons he'd like to be...

The topic of Playboy and visits to the mansion (which is nothing like it is today) have been common talk. More importantly, interviews with various playmates have been a mainstay. This includes Hugh's former wife, Crystal Harris. And she said some things that Hugh deeply resented.

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In 2011, Crystal Harris decided to come on The Howard Stern Show and be interviewed by the enormously successful radio host. For those who don't remember, Crystal started working for Playboy in 2008 and subsequently got engaged to Hugh. Of course, this got tons of press because he was a whopping 60 years older than her... not to mention the fact that he was her boss. But this was totally in line with the lifestyle that Hugh led. Of course, this eventually came around to bite him in the a**!

Hugh and Crystal hit a major rough patch in 2011 when she broke off their engagement just five days before the wedding. While the press said things were amicable, that was clearly a lie.

After the breakup, Crystal decided to go on The Howard Stern Show and 'tell-all' about what went down in their bedroom. Among the many things she said in the 2011 interview, Crystal claimed that she and Hugh only had sex once over their two-year relationship and that it only last for "two seconds". Additionally, she claimed that she wasn't attracted to him at all. "I’m not turned on by Hef, sorry," she told Howard and his co-host, Robin Quivers.

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Of course, a lot of this was met with backlash. Not just because of the comments she made about Hugh, but the fact that she was running around promoting herself after the split. Clearly, all of the negative press that Crystal received got to her (or her publicists) because...

Crystal Made A Public Apology

After her newsworthy appearance on The Howard Stern Show, Crystal seemingly figured out that she may have said too much. According to The Hollywood Reporter, she took to Twitter to apologize and explain what happened when she sat down with the self-proclaimed King Of All Media. "The Stern interview scared me, he’s harsh," Crystal Harris Tweeted out to her fanbase and everyone else absorbing the story. "I was unprepared and blurted out things I shouldn’t have said, I’m sorry."

But even though Crystal foisted the blame onto the legendary shock jock, her famous ex (at the time) clearly didn't take the bait. Instead of ruining any sort of relationship he had with Howard, Hugh Hefner totally blamed Crystal for what she said on his show, even though he did publically accept her apology.

"I don’t blame Howard. Crystal shouldn’t have been booked on the show at this sensitive time," Hugh Hefner said publically. This was followed by, "I think Crystal told Howard Stern what he wanted to hear."

And that's exactly right. Howard and his team clearly booked Crystal Harris on his show because they knew that she would talk about Hugh due to their split. The Howard Stern Show was, and still is, one of the best places to make headlines. Hugh went on to Tweet that, "Crystal convinced me that she adored me. That was the first lie."

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While Hugh rejected all of the claims that Crystal made in her interview with Howard, he didn't focus much on the radio host at all which is something he totally could've done. Fortunately for Howard, Hugh didn't want any bad blood. He excused Howard's line of questioning and just blamed Crystal, who he later forgave and reconciled with. Clearly, Hugh didn't take it all TOOO personally (or learned to forgive, at the very least) as he stayed with Crystal until he died in 2017.

Next: Why Howard Stern Thinks He Ruined His Vacation With Emily Blunt And Jimmy Kimmel