Some of the Stern Show's most candid interviews have occurred when Chelsea Handler sits down with Howard. Over the years, the comedian has never held back while discussing her personal life, her career, or who she does and does not get along with in Hollywood.
Check out all of the many highlights from Chelsea Handler's visits ... previously on the Stern Show.
During her 2016 Stern Show visit, Chelsea talked to Howard about taking topless Instagram photos and how she really feels about her breasts.
"Any girl who has big boobs hates them," she told Howard. "Psychologically I had an issue with my boobs being too big; I always try to minimize them." She also shared her secret for how she keeps her boobs looking their best. "I've never had a baby and I wear a bra to sleep every night," Chelsea said.
Pals With Penn
Chelsea hangs with several Hollywood A-listers and in 2016 she told Howard about her good pal Sean Penn. "Sean is a friend of mine, I like him … he's very funny," Chelsea said. "He also takes himself very seriously. I didn't know he was a journalist. What the fuck is that?"
Chelsea was of course referring to when Sean stunned the world by interviewing notorious Mexican drug lord Joaquín "El Chapo" Guzmán.
"I just didn't understand why he was there. Like, if you were going to get some blow, OK, I get that," Chelsea joked.
Getting Rejected by Her African Tour Guide
As documented in "Uganda Be Kidding Me," Chelsea took an eventful trip to Africa. During her 2014 Stern Show appearance, Chelsea talked about drunkenly hitting on her tour guide, Rex, only to get rejected by him.
"The thing with him was he had a girlfriend ... and I didn't take that seriously," Chelsea told Howard. "I respected him more when I found out he rejected me because of that."
Fortunately, the incident didn't make the rest of the trip awkward and Rex is heavily featured in Chelsea's book.
Confronted by Prior Celebrity Punchlines
Chelsea also discussed recently attending Madonna's very exclusive Oscar party. Howard asked Chelsea if she gets confronted at these sort of parties by people she's mocked on her show. She cited a time when that exact thing happened, recalling the time she was approached by Yankees third baseman Alex Rodriguez.
"He comes up and is like 'Chelsea, why you gotta make fun of me all the time?' and I'm like, 'Get away from me, I think you're disgusting," Handler said.
Despite Alex telling Chelsea that he was a big fan, Chelsea maintains that he's a "fucking asshole." When Howard asked why, Chelsea responded: "Just the way he conducts himself; he's got a centaur of himself in his bedroom!"
Moving Away From Late Night
After so many years on E!, Chelsea told Howard that she had grown restless. "I feel like I'm smarter than what I'm doing, and I feel like I'm getting dumber," she explained.
Once she departed from E!, Chelsea was courted by many networks, but she desired a freedom that couldn't be offered from a traditional television structure. Finally, she thought of Netflix.
"I went to Netflix. I went to them," Chelsea said.
Howard wondered if this move was her attempt at reinventing herself and getting away from the talk show game. "I was bored," Chelsea said. "I have a lot of interests and I want to educate myself in a kind of humorous way and take my audience with me on that. I'm done with interviewing celebrities. There's nothing left. I'm not interested."
Tune in Tuesday to hear Chelsea Handler's return to the Stern Show