David Letterman Revisits Howard Stern Feud on ‘Jimmy Kimmel Live!’: “Arm’s Length Might Be the Way To Go”

Jimmy Kimmel has only been in Brooklyn for two days and he’s already stirring up old trouble! Former late-night host David Letterman stopped by Jimmy Kimmel Live! on Tuesday (Sept. 27) to discuss his rocky friendship with Howard Stern.

Letterman recalled knowing Stern for “a very, very long time” as they worked in the same building when The Late Show with David Letterman started. He said, “In those days, Howard was ‘shock jock’ Howard and I was always afraid of Howard because I didn’t want Howard to say unpleasant things about me.” (But as we all know, he did.)

The two got into a squabble after Stern dissed Letterman and his wife on The Howard Stern Show. Letterman expressed, “I kept thinking to myself, he must not have any feelings of his own. He’d say hurtful things and the more hurtful things he’d say the greater his audience would become. I thought, ‘I’m in the wrong business.'”

This isn’t the first time the feud has been brought up in retrospect, and thankfully, things seems to be resolved. Stern addressed the feud on Netflix’s My Next Guest Needs No Introduction with David Letterman in 2018.

“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,” said Stern. “I could not love anyone. I couldn’t respect anyone. I just thought this was who I was.”

The radio host examined his life to pay focus on “what was good,” one of which being his relationship with Letterman. “I could appreciate what you did for me. I had betrayed your trust and I was ashamed. The reality was: I loved you,” explained Stern.

Letterman spoke to Kimmel about his current relationship with Stern, saying, “I’ve gotten to know him as a completely different guy and that’s the guy that I have really gotten to be friends with over the years.”

The former host wrapped up the topic with a story about Stern sending him a text of one of his paintings. After texting and calling to compliment his work, Stern informed him that it was sent by mistake.

And what was Letterman’s takeaway? “I love Howard, I just think arm’s length might be the way to go here.”