He also stood up for Meghan McCain and talked about trying to land an interview with Hillary Clinton.
The radio personality appeared on the morning show to promote his new book, "Howard Stern Comes Again," which is filled with celebrity interviews from his past, as well as new commentary on them and his shift away from his "shock jock" origins.
Speaking about some of his favorite interviews included in the book, he brought up Rosie O'Donnell, who used to be a cohost on "The View" and recently had some choice things to say about moderator Whoopi Goldberg.
"I actually talk about Rosie in this book, Rosie O'Donnell, and Rosie, one of the best guests I ever had on my show," he recalled. "It was a miracle she was on my show, because for years I had, like an ass, attacked Rosie. I never gave her a chance."
"So Rosie and I, we talked and I realized it was just my own anger," he explained. "But the interview I did with her in the book, she came in, she was so open and it leveled me. She began to talk about, and it was a really intimate conversation, having lost her mother at a very young age and she was in so much pain she starts to describe she would take a small baseball bat and break her hands."
With sympathy in her voice, Joy Behar said, "Poor girl."
"I said why, why do you do something like that? She says because I was in so much pain after the loss of my mother, I wanted to feel anything else," Stern continued. "I thought, ugh, such an honest moment and the fact that she's sharing it with the audience."
He went on to say he and O'Donnell became friends, with her reaching out with suggestions when he took up painting. "It's a beautiful interview and even talking about her climb in show business is quite phenomenal," he added.
"Let's change the subject for a second," Behar then said. "What's the matter, you don't want to talk about Rosie?" Howard asked.
"No I do, you did, it was very good," she replied with a laugh. "What happened to Rosie?" he then asked, "she's not on the show anymore." After Behar added, "She's around," Stern then turned to Goldberg and asked, "Whoopi, you're anti-Rosie or you like Rosie?" Whoopi's response: "I don't think about it."
With Behar explaining that it's "not like a two hour show," they then moved on. "it's not like a two hour show."
Through the conversation, Stern touched on some of his other celebrity interviews, including one with disgraced movie mogul Harvey Weinstein. Appearing on Stern's show, Weinstein shot down any "casting couch" accusations, something Howard said he believed was a lie at the time.
"I did. I did. At the time, I kinda did [think he was lying]," he said. "I got off the air ... and said I don't know that I buy that."
"I was a huge Hillary Clinton supporter. I was for her before Obama, I loved Obama, but I loved Hillary Clinton," he explained. "I thought she was a candidate that was misunderstood, that her message wasn't coming across. I think if she would have come on the show -- I was begging her, I didn't talk to her directly, I think she was afraid of me and justifiably -- she played it safe. That's the warning to whoever becomes the Democratic nominee, don't play it safe."
He added he's voted red in the past, before telling the cohosts to give Meghan McCain a break.
"I feel bad. I see you getting yelled at all the time," he said to her. "Anytime you're feeling overwhelmed, let me know. Give the woman a chance, for God's sake. She's in tears!" That really perked up Meghan, who shouted, "Yeah, listen to Howard!"
Sunny Hostin also shared a good moment with Stern as well, explaining that she found his old radio show "so offensive, I was turned off by it" -- but then added, "you're a very different person today and I loved your book and I believe people evolved."