Chelsea Handler on Telling Jokes With Dave Chappelle, Putting Herself Out There With Andrew Cuomo, and Why She Absolutely, Positively Doesn’t Miss Late-Night TV

Chelsea Handler has evolved considerably in recent years, as the title of her new stand-up act suggests, and she wants the world to know it. The 45-year-old actress, comedian, and talk show host returned to the Stern Show on Wednesday, opening up about subjects ranging from drug use and dating to why she was nervous to return to stand-up after six years away from the mic. She didn’t shy away from candidly reflecting back on the wildest aspects of her life, but when it came to her career she said she’s only interested in moving forward.

Considering the immense popularity of “Chelsea Lately,” her TV show which ran for eight seasons on E!, Howard wondered if she ever regretted leaving late night. She didn’t.

“Why would I want to stick with that?” Chelsea told him. “There’s no evolution there. That’s me in one format doing one thing that wasn’t that interesting to me.”

“What’s the rush to get away from it?” Howard wondered.

“I had outgrown it. That’s not to say I won’t ever do it again. At that time in my life, it wasn’t interesting and I was irritated all the time. I needed a break,” she said. “I feel like my work since I left that show has had such a high level of integrity, you know? My book and my documentary and my docu-series and my shows on Netflix and this special, especially. It’s like I’m working at a higher frequency than I was when I was just kind of winging it.”

Chelsea told Howard leaving late night behind has also helped her grow as a person. “I’m not a self-absorbed lunatic anymore,” she said. “I had to remove myself from that situation to get myself in better headspace.”

Late night may be a thing of her past, but the entertainer assured Howard stand-up is still very much a thing of her present. In addition to her new HBO special, Chelsea recently participated in Dave Chappelle’s star-studded comedy spectacular “Dave Chappelle & Friends: An Intimate Socially Distanced Affair.” Howard was curious what drew her to the event, held near Dave’s home in Yellow Springs, Ohio.

“I was driving across country over the summer with a couple of girlfriends and we were going through Ohio, so I stopped for a night and stayed there and did a set,” she said, explaining comedians Michelle Wolf, Ali Wong, and Donnell Rawlings were also in attendance.

“[Chappelle has] created like a whole city down there and you get tested when you get there and you get a bracelet and everyone with the bracelet is able to mingle,” she continued. “It’s like a disco from the ‘70s. It’s just so much fun and everyone just parties until around six in the morning, so I had to get the fuck out of there after the first night because I was like, ‘Whoa, whoa, whoa whoa—I can’t operate like that anymore.”

“Does Chappelle put you up for the night?” Howard asked.

“He has a house and guest house, and I had my dogs with me—my rich, white lady dogs, as they referred to them as. I spent the night at his guest house,” she said.

Chelsea only spent one night at Dave’s but several of her colleagues apparently plan to stay in the neighborhood longer. “There are comics that have moved down there because that’s the only stage time there really has been, you know?” she said. “There’s like a group of comics who are down there thinking about buying property and stuff.”

“I think Chappelle [is] going to turn it into something bigger one day,” she added, saying his comedy events draw a crowd of 450 people every night.

Thankfully, Chelsea’s fans needn’t travel to Ohio to watch her perform. Her latest stand-up special “Evolution” is streaming now on HBO Max. The special has been well received, but Chelsea admitted returning to the stage after such a long hiatus made her nervous. “I didn’t even know if I could sell stand-up tickets, you know? I hadn’t done stand-up in like six years,” she said.

She told Howard she started off by performing at small theaters to get her footing back and then eventually embarked on a 40-city tour. “I already had the show in very good shape but I just needed to work it out,” she explained.

Chelsea kept the comedy going after COVID-19 hit and sometimes wound up telling jokes in front of audiences in no mood to laugh. “It was humbling to come back to stand-up and it was also humbling to do these practice shows … to perform in front of fucking 30 people who were socially distanced,” she said. “I was bombing, pretty much, the first 10 shows.”

“I’m not going to lie, it was hard,” she continued. “Emotionally and intellectually, it was definitely hard.”

But everything worked out in the end. “I knew that night of the special it would be great and it was. That’s how it always happens. You have to struggle,” she said.

While Handler’s lifestyle and comedy routine have certainly evolved, she’s not done joking about dating, womanhood, and the pleasures of the flesh. Her new special has one bit about shaving her face in the shower and on Wednesday she told Howard it’s something she actually does.

“I’ve turned on many of my girlfriends. They also now shave, too,” she said. “If somebody has a hairy face I’ll tell them and say, ‘Hey, listen, there are ways out there to get rid of the hair on your face and this is one of them.’”

Chelsea also said romance has become trickier since the onset of quarantine. She recently met a man on the celebrity dating app Raya, but their date didn’t go as she’d hoped. “I had a guy come over the other night but then he told me he didn’t believe masks work, so I couldn’t have sex with him,” she said.

Nevertheless, she refused to quit trying. “I have someone coming over later tonight, so maybe we’ll see what happens,” she said. “I haven’t met him yet. It’s a first timer.”

One man who probably wouldn’t be coming over any time soon was New York Governor Andrew Cuomo. Chelsea copped to crushing on Gov. Cuomo in recent months, going so far as to speak about it on “The View” and in her new special, but on Monday’s Stern Show the governor revealed to Howard he couldn’t get involved with her because Chelsea lived across the country and would need to quarantine during her visit. “I need a date who is not quarantined. Can’t have somebody come and stay on a date for 14 days,” Gov. Cuomo had said with a laugh.

Chelsea felt the governor’s response should’ve been more gentlemanly. Regardless, she was proud of herself for boldly making the first move. “I wanted to say to women, like, ‘Let this be a lesson … Yes, it’s okay, we can keep going. Also, put yourself out there and take a risk. It’s fun to take risks. Even when we get rejected, these men don’t define us,’” she said.

Howard wondered how Chelsea had developed feelings for Gov. Cuomo in the first place and she said his leadership during the COVID-19 crisis was mostly to blame. “It was in the moment. It was like he was coming in to rescue us and we had no leadership,” she said. “I wanted to flatten his curve and have him flatten my curve and then I wanted us to apex together.”

“We had funny repartee [on social media] …. I’d write inappropriate things and then he would call me and be like, ‘What are you doing?’ What kind of person writes something like that?’” Chelsea continued. “It was cute, it was funny, but then he had to ruin it by saying he didn’t want to be around me for 14 days.”

After considering it a little longer, Chelsea wondered if Gov. Cuomo could even handle all she had to offer. “Do you think he’s up for a night with me?” she asked co-host Robin Quivers. “Do you think he’s physically, stamina-wise, up for it?”

“Oh yeah!” Robin responded.

“Of course!” Howard agreed with a laugh. “He’s a New Yorker. He grew up in a rough and tough neighborhood.”

“Chelsea Handler: Evolution” is available now on HBO Max.