In an appearance on Letterman's Netflix special, My Next Guest Needs No Introduction, Stern, 64, was forced to explain his past and consistent criticism of the host in an awkward exchange.
"I had to stop listening to your show early on — because I heard myself being talked about in unflattering ways," Letterman, 71, admitted. "And I thought, 'holy crap, I don't need this!' Then I thought 'well maybe if I have him on the show, he'll stop saying these things. Maybe if I called him, he'll stop saying these things.'''
"But something happened and you and I became friendly or friends — the way I always thought we would be. And for a myriad of reasons, I received a heartfelt apology. What was the change?" Letterman asked.
The radio mogul admitted that his resentment towards Letterman was a culmination of jealousy, envy, and self-esteem issues.
"I've apologized to a lot of people and I'll tell you why. I think I did a lot of growing up, and I do attribute this to psychotherapy," Stern began. "Again, I was just a young man full of rage, and I was angry. I was angry with you that you were on television — that you had an audience. There was no rhyme or reason to it. I could not love anyone. I couldn't respect anyone. I just thought this was who I was. And I went into psychotherapy. "
Letterman admitted that he felt "eviscerated" by Stern's attacks, not only on him but on his wife, Regina Lasko. In response, Stern had created a painting of a flower for Lasko.
"Words had no meaning to me. Words didn't hurt," Stern further explained. "Of course they hurt me if somebody said something bad about me. But as far as I was concerned, everything was a joke. Words don't mean anything."
"'Why am I hurting this guy I love so much and admire?" Stern asked himself. "Really this is someone that maybe I could talk to and relate to – because we have been in the business a long time; and maybe he could teach me something."
The two made up in 2011 when the Shock Jock made an appearance on Letterman's show where he then publicly apologized.
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