Chelsea Handler sat down with Howard Tuesday morning to discuss her upcoming Netflix docu-series "Chelsea Does." The wide-ranging interview also touched upon the comedian's sex life, smoking weed with Willie Nelson, and recent comments made against her by comedian Heather McDonald.
Here are 10 of her greatest revelations:
Heather McDonald Is 'So Full of Shit'
Comedian Heather McDonald, a former "Chelsea Lately" contributor, recently said she was "living in fear" of Chelsea when they worked together on E!'s "Chelsea Lately."
"She's so full of shit," Chelsea told Howard on Tuesday.
Chelsea said Heather had lost her trust years ago after selling Chelsea out to the media: "I found out at work that she was trading stories to US Weekly about my personal life in exchange for having her photos run in the magazine."
Handler added that McDonald probably "did eighty things she should've been fired for," but said she didn't fire her because "she was good on the show and she was funny."
Chelsea also wasn't sure why Heather didn't leave the show if she felt so afraid on the job. "It's not an internment camp," she fumed. "If you're that fearful, then get [another] job."
On Breast Maintenance and Plastic Surgery
Chelsea told Howard that she's never had plastic surgery, despite the fact that many people think she's gone under the knife: "I don't do botox," she said. "I have a little filler under my eyes, but I've never done plastic surgery … I've had a little stuff filled in … but nothing heavy."
Chelsea later spoke about her boobs, which she's bared on social media several times in the past.
"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."
When Howard insisted that her breasts still look great at 40, she filled him in on her gravity-defying secrets: "I've never had a baby and I wear a bra to sleep every night," Chelsea said.
Handler said the real issue no one is discussing is how hard it is for men to get penile enlargements. "I want women to do whatever they want to feel good about themselves, but I don't think it's fair that guys don't have more penile enlargements," she said. "It's so unfair to men that they cant get a proper enlargement."
Swapping E! for Netflix
Chelsea pulled the plug on her own E! talk show almost two years ago because it wasn't fulfilling her intellectually, leaving to do something smarter and different with Netflix.
"Do you have any regrets?" Howard asked.
"No," she confidently answered.
Howard wondered why Chelsea wouldn't just stay at the network and try revamping her show instead of starting over from scratch. "I was already annoying myself on that show," she said. "I didn't want to start annoying other people on top of myself."
She said one of the reasons her new docu-series is great is because she gives up control for the first time in awhile. "For me it was a great departure," she explained. "Just slap me around like a bitch. I don't want to be in control, I don't want to make decisions … Just make me your bitch … And they did."
"I haven't been this proud of something in a long time," she added.
Doing Drugs With Willie Nelson
One of the upcoming "Chelsea Does" episodes is all about drugs. So, naturally, Chelsea does a bunch them.
From the trendy psychedelic ayahuasca to smoking weed with legendary marijuana enthusiast Willie Nelson, she tries a bit of everything.
"I would've done heroin if they allowed me to," she revealed to Howard. "I wanted to illustrate what people look like. It's very rare ... Everyone takes ambien and combines it with alcohol. You don't know what you look like; I wanted to illustrate that."
She said lighting up and smoking a joint with Wilie was actually kind of stressful.
"I was so high that I was just looking at him and thinking, 'I hope he says something else because I don't know what to say,'" she said. "I couldn't think of any questions and I was just so stoned …. This is gonna be a disaster."
Chelsea said making the docu-series was great, but there were a few very embarrassing moments for her -- one of which, she detailed.
"At one point during the drugs doc, we're sitting around dinner and ... talking about addiction," she told Howard. She said she asked them whether or not they had ever thought she was an addict and they said, "yes." In fact, they were so worried about her that they actually once planned to hold an intervention.
On Her Dad Meeting Ex-Boyfriend 50 Cent
Chelsea admitted that her father, who appears on her new Netflix show, is completely "racist."
"He thinks he's not racist because he likes to hit on black women," she explained.
Chelsea admitted that her dad didn't like one of her ex-boyfriends, the black rapper 50 Cent, but didn't necessarily chalk that up to his racism: "My dad doesn't like anyone I've dated, though."
Howard wondered whether she dated black men just to piss her pops off, but she said it has nothing to do with her dad. "If I meet a hot black guy and he's smart, of course I want to date him and fuck him," she said.
A Year Without Sex
From there the conversation turned to her sex life and Chelsea shocked Howard by telling him she went a full year without having sex.
"I wasn't trying to not have sex," she told Howard. "There was nobody I was interested in … I need to have sex with somebody I want to have sex with."
Eventually nine months had passed and one of her friends convinced her it would be cool to stay abstinent for a full year. So Chelsea waited a few more months before finally getting down. "The sex I had afterward was pretty amazing," she admitted.
Ex-Boyfriends, Cheating, and the Ménage à Trois
Dating and sex is also a topic of conversation on her upcoming Netflix series. In one episode she interviews her ex-boyfriend on camera, a "guy named Peter."
"He was my first boyfriend, when I was 21 and waiting tables in L.A.," she told Howard.
She also interviewed the guy who runs Ashley Madison, which Howard found curious.
"Because he's a fucking asshole," she explained. "Anyone can do whatever the fuck they want, but tell people ... so they have an opportunity to decide what they want."
Howard wondered whether she had ever been unfaithful.
"I don't cheat," Chelsea said. "I've dated guys at the same time, but I don't lie."
The topic of conversation eventually switched over to whether Chelsea had been with other women. She said she's not bisexual, but that she's "hooked up with a girl or two … just threeways with guys over the years."
Current Boyfriends and Getting Knocked Up
Now that Chelsea's year of abstinence is over, Howard wondered whether she was dating anyone new.
"I'm single," she told him. "I'm not having sex with anybody on the regular."
Chelsea said she's dating intermittently, but mostly just as favors to friends trying to set her up. "If I really wanted a boyfriend, I'd have one in a second," she said. "But I don't ever want to operate on the basis that that is going to fulfill me."
The two later discussed child-rearing, which Chelsea doesn't want any part of.
"I just don't want to take anybody to the zoo," she said. "I don't want to go to Disneyland. I don't want to go to Color Me Mine ... Don't be a mom if you can't be the mother you would've wanted," she added.
On Sean Penn Interviewing El Chapo
Actor Sean Penn recently surprised the world and also her friend Chelsea by interviewing wanted criminal and notorious Mexican drug lord El Chapo.
"Sean is a friend of mine, I like him … he's very funny," she told Howard. "He also takes himself very seriously. I didn't know he was a journalist. What the fuck is that?"
"Why would he be there?" she wondered. "If he was going to get some blow that's one thing."