The Untold Truth Of Chelsea Handler

Chelsea Handler, according to a brief bio from her agency, United Talent Agency, is "one of the most successful figures in entertainment today," with her "talk shows, best-selling books, and stand-up comedy" earning her "millions of fans worldwide."

A native of New Jersey, Handler was still a teenager when she headed to Hollywood to pursue a career in showbiz. She quickly gravitated to stand-up comedy, eventually becoming a fixture in the Los Angeles comedy circuit until being hired by the E! network in 2006 to star in her own sketch-comedy series, The Chelsea Handler Show. While that show flopped, her next venture did not: Chelsea Lately, a late-night talk show, ran for seven successful seasons until she left the network and signed a deal with Netflix. That deal included a comedy special, Uganda Be Kidding Me Live, several Chelsea Does... documentaries, and another talk show, simply called Chelsea, which ran for two seasons. 

Sitting atop the comedy food chain, Handler has indeed become one of the most successful performers in her field, but there's a lot about this famously funny lady that even her most ardent fans may not know. Let's discover the untold truth of Chelsea Handler. 

Just two years after a 19-year-old Chelsea Handler moved from Livingston, N.J. to Los Angeles with a goal of becoming a star, she was arrested for drunk driving. Her arrest, she told Barbara Walters in a 2014 interview, proved to be a pivotal moment. 

"I had to go this class, like DUI class, where basically you had to speak publicly about your experience and your arrest," Handler explained. "And at that time in my life, I had never had to speak publicly. And then I did it ... and I was higher than I've ever been. I mean, everyone was laughing at my story. And somebody said, 'You should be a stand-up comedian!' I'm like, 'Maybe I should!'"

As Handler said in an interview with CNN, speaking in front of the class "helped my career go in the right direction and luckily I didn't injure anybody on my way." She also explained why she wouldn't be getting another DUI, quipping, "I have a driver, luckily — in every city, because I'm so successful."

Back in 2010, Radar Online obtained Chelsea Handler's alleged "graphic" sex tape, which was reportedly made about 10 years earlier. According to the outlet, the tape begins with a "fully clothed" Handler performing her stand-up comedy act, and then cuts to her appearing naked in bed with an unidentified man, apparently doing the deed. The tape then cuts back to the comedy routine. 

A source claimed to the outlet that the tape was actually "a demo tape" that Handler sent out to "a bunch of talent agents and managers" in hopes of landing on their radar. In fact, the insider pointed out that it was "highly possible" that most of the people who received that tape only watched the first few moments "and missed the sex tape part altogether."

Handler later addressed the leaked footage during a monologue on her E! talk show, Chelsea Lately. "I would like to say to Radar Online: A. Thanks for ruining my surprise Christmas gift to my staff," she joked, adding (via the New York Daily News), "Number two, it was made as a joke. I put it on an audition tape for a comedy club, because I'm a comedienne, and I've been showing it at birthday parties for f**king years!"

During a joint interview with Parks and Recreation star Nick Offerman for Esquire in 2015, Bill Cosby's name came up. Discussing the disgraced comedian, who later received a prison sentence of three to 10 years after being found guilty of sexual assault, Handler revealed that she was once nearly "Cosbyed."

About a decade earlier, she and Cosby were both in Atlantic City to perform at the same hotel when she received a message that Cosby wanted her to pay him a visit in his suite. Feeling that request was "really weird," she accepted the invitation — but brought along three male friends. 

"And thank God I did, because now I know what would've happened if I went up there alone," Handler said, referencing the 60 accusers who came forward, detailing The Cosby Show alum's alleged efforts to drug and rape them. "Then my friend texted me the other day saying, 'Do you remember that night we went up to, or that afternoon we went up to Bill Cosby's and you were so freaked out you made us come with you?' And I said, 'Yeah,' and he said, 'Hello! You could've been one of his victims if we weren't there,'" Handler recalled. "And I went, 'Oh my gosh...' Yeah, so yeah, he's guilty."

In 2016, Chelsea Handler got uncharacteristically serious in an essay she wrote for Playboy about abortion rights, recalling how she discovered she was pregnant at age 16. 

"I hated my parents and I was having unprotected sex with my boyfriend, who was not someone I should've been having sex with in the first place, never mind unprotected sex," Handler wrote. Well aware that she "wasn't really playing with a full deck of cards" at the time, the comedian pointed out that the notion "that I would have a child and raise it by myself at that age, when I couldn't even find my way home at night, was ridiculous." As Handler continued, she revealed that her parents took her to Planned Parenthood to terminate the pregnancy. "And when it was over, I was relieved in every possible way," she added.

Handler then had a second abortion when she became pregnant again that same year. "Getting unintentionally pregnant more than once is irresponsible, but it's still necessary to make a thoughtful decision," she noted. "We all make mistakes all the time." Sharing her belief that, ultimately, the decision rests with each individual woman, Handler defiantly concluded, "I'd love for somebody to try to tell me what to do with my body. I dare them."

Chelsea Handler regaled shock jock Howard Stern with a weird Hollywood anecdote when she appeared on his satellite radio show in 2014. As readers of her book, Are You There Vodka? It's Me, Chelsea, may have gathered, this comedian's not averse to bolstering a good time with some alcohol and drugs. That was what happened when she joined pal Jane Fonda for one of the Oscar winner's "dance parties," Handler revealed.

"I went over to Jane Fonda's house one night and I did a Quaalude," Handler told Stern (via the Toronto Sun), revealing she had never taken one before when a friend offered her two of the pills. "So I took both of them and that was a disaster," she admitted, adding, "Every time I'd get up I'd fall back down!" When Handler told her host about what was going on, the Hollywood icon proved to be surprisingly chill about the whole thing. "I told Jane that I took two Quaaludes and she said, 'Well, then you better sit down and not get up for awhile,'" Handler said. "She didn't care. She's super cool."

Loyal viewers of Chelsea Lately will no doubt remember Heather McDonald, a writer on the show who also made frequent onscreen appearances. However, she raised her boss' hackles when Chelsea Handler discovered her fellow comedian had been leaking salacious gossip about her to tabloids. Yikes. 

When Handler appeared on The Howard Stern Show in 2016, she was asked to comment on a New York Daily News report, in which McDonald claimed she "lived in fear" of Handler while working on the E! show. "When I found out at work that she was trading stories to Us Weekly about my personal life in exchange for having her photograph run in the magazine ... I could have fired her," Handler said. "I did not fire her. She had a job for four more years. I never hung out with her personally again." 

During an appearance on Watch What Happens Live's after-show a year later, an audience member asked Handler if she and McDonald had "settled" their feud. Insisting the whole thing had been "blown out of proportion," Handler responded, "I don't have a feud with her ... She's a girl. I don't fight with other girls."

While regular people looking to hook up can avail themselves of such apps as Tinder, Bumble, and Grindr, celebrities have their very own dating site that allows them to meet up with other rich and famous folks. Called Raya, the app has been used by celebrity singletons like Channing Tatum, Lizzo, and, yes, Chelsea Handler.

She made that admission in a 2017 discussion with Howard Stern on his SiriusXM morning show. Telling the longtime host that she'd hooked up with a stranger in London a few months earlier, Handler explained that she'd used "that dating site Raya" to connect with her one-night stand. "I did have sex with a celebrity like a year or two that you'd be interested in, but I can't talk about him," Handler went on to tease. Stern's curiosity was piqued, but Handler held fast, only revealing her paramour was both "a comedian and an actor." According to Handler, she and the mystery celeb knocked boots "five or six times and it was really fun," but wrote the experience off as "drunken escapades."

It's said that everyone has a doppelgänger, someone somewhere who looks exactly like you. While this may or may not be true, Chelsea Handler can lay claim to be mistaken more than once for actress/director/game show host Elizabeth Banks. During a 2011 appearance on Chelsea Lately, Banks revealed she is not unaware of the confusion.

"I was sitting in Toronto and a guy walked up to me and said, 'Oh my god, my girlfriend loves you. She would die if I didn't get your autograph. This is so exciting!'" Banks told Handler (via Us Weekly). "He's like, 'I just love your books. I mean, My Horizontal Life....' I was like, 'Oh, he thinks he's meeting Chelsea Handler.'" However, the Pitch Perfect star decided to go with it. Explaining that she didn't bother trying to correct the mistaken fan, Banks quipped, "I couldn't ruin it for him!"

Handler joked about the resemblance in a tweet she issued prior to Banks' Chelsea Lately visit. "Elizabeth Banks is on tonight's show, so all my dreams have come true," Handler tweeted. "I can now say I've interviewed myself."

In 2010, rumors began flying that Chelsea Handler was dating rapper 50 Cent. Two years later, the comedian confirmed that they actually had been an item during an appearance on The Howard Stern Show. "He's actually a lot different than you'd think ... He's like a big Black teddy bear," Handler said of their short-lived romance. "I thought it was kind of amusing that I would even be with 50 Cent. I thought it was funny ... It's fun for a little hookup, but it's never going to be anything serious."

In fact, 50 Cent later added some details about his time with Handler when he appeared on the same show in 2017, with Stern asking what Handler was like in the sack. "Tell her I call her 'gator,' she'll know what I'm talking about," the rapper said, elaborating by equating making love with his ex to "wrestling a gator." Asked by Stern whether he was "in love" with Handler, the rapper replied, "She's cool, man." However, 50 Cent insisted he wasn't going to answer that question, quipping, "'Cause I got a reputation." 

Before becoming a comedian and talk show host, Chelsea Handler was once an aspiring beauty pageant queen. As she told Jay Leno during an appearance on The Tonight Show, she actually competed for the crown of Miss Teen New Jersey. 

"Aw, look at my hair, that's so cute," Handler said when shown a vintage photo of herself all dolled up for a pageant, her coiffure teased to voluminous heights. "I look like the Lion King." However, Handler admitted that she quickly became disenchanted with the pageant requirements. "You know, you have to be in a bathing suit, and then they want you to play an instrument, and that wasn't gonna work," she said. "I mean, I played an instrument, but it was called a bong."

In 2019, Handler took a lie detector test for Vanity Fair, and revealed that while she did not win the pageant, she "came in top 15." Admitting she entered the competition for neither world peace nor money, the comedian declared that the reason she competed was for "the recognition that I was beautiful — and that I could use an entire bottle of Aqua Net on my head in one sitting, and go out in a prom dress or a gown or whatever the f**k I wore, and kill it."

In 2011, Chelsea Handler's autobiographical bestseller, Are You There Vodka? It's Me, Chelsea, was adapted as an NBC sitcom (although the unwieldy title was eventually shortened to just Are You There, Chelsea?).

Handler's fans were likely confused when they tuned in and saw that the titular Chelsea was played not by Handler, but by That '70s Show's Laura Prepon. Handler, however, did have a role on the show — but as Chelsea's overbearing older sister, who welcomes a baby in the series' pilot. 

Unfortunately, the new comedy was not well received by either viewers or television critics. According to a review in Mother Jones, Are You There, Chelsea? "[plumbed] new depths of bad sexist drivel," while The Atlantic asked, "Could anything have prepared us for what lurched onto the screen and just about died with a wheeze and a rattle before us last night?" As the outlet pointed out, the show had been "plagued with problems" from the get go, with three members of the original cast fired and an entirely new pilot (featuring a different plot) filmed. All that retooling made little difference; the show was ultimately cancelled after just one season. 

Chelsea Handler's dog, Chunk, was nearly as famous as his owner; in fact Chunk's Twitter account (yes, a dog with a social media presence!) boasts an impressive 100,000-plus followers. 

Handler opened up about Chunk, a regular presence on her Instagram and Twitter feeds, during a visit to The Rachael Ray Show. "I try to bring him wherever I can, but you have to quarantine dogs when you take them to other countries," she explained, noting that a friend tried to convince her to claim Chunk was a service dog. "People know who I am, they know that I'm lying," Handler continued. "She said, 'You can pretend that you're blind.' I'm like, 'I can't pretend I'm blind.'"

In early 2018, Handler took to social media to share some sad news. "This guy passed away today," she wrote in an emotional Instagram post, which featured a photo of Chunk. "... My chunky monkey. I love you, baby. Softest doggy in the world," Handler concluded, describing Chunk as "a true gentleman." Handler, who later told InStyle that she has "true, unconditional love" for her pets, has since adopted two new dogs: Bert and Bernice.

In 2014, Chelsea Handler revealed to Howard Stern that she was exiting E!, with The Hollywood Reporter noting that she described the network as "a sad, sad place to live." She added, "They don't know what they're doing, they have no ideas. It's a failure." Yikes.

So Handler bid farewell to E! and said hello, Netflix! According to THR, Handler signed a lucrative "megadeal" to host a talk show for the streaming service. "I wanted to sit with the cool kids at lunch, so I approached Netflix to make sure they were as cool as I thought they were," she stated. "And when I confirmed my suspicions, like with any other future lover, I made my move." Handler even managed to get in a dig at E! and its reality-heavy lineup when she described Netflix as "the most forward-thinking, alert group I've sat down with in ages. No offense to the Shahs of Sunset."

Handler was even more straightforward about her disdain for E! when she spoke to Fast Company two years later. "You're a reflection of the company you keep, and I wasn't impressed with anybody," she said of her "incredibly frustrating" experience with the network. "I just wanted to leave, to be somewhere else."

Thanks to that lucrative Netflix deal, her many years on E!, and writing all those bestselling books, Chelsea Handler has become quite a wealthy woman. According to Celebrity Net Worth, the comedian's Netflix contract was earning her $10 million a year, and she boasts an estimated net worth of $35 million, as of this writing in 2020.

While speaking with Inc. in 2018, Handler explained the work ethic that has made her a multimillionaire in just seven words: "When you make a commitment, keep it." That philosophy, she explained, extended back to her days waiting tables. Admitting she wasn't the greatest waitress, Handler did manage to gain a reputation for saying "yes" whenever somebody else needed a shift covered. The TV star carried that same attitude with her into comedy clubs when she started performing stand-up. "I kept showing up," Handler said. Noting that this ultimately "permeated every facet of [her] life," she added, "Whether it's wanting to cancel a workout, a friend's party, a public appearance, my family in New Jersey. Whatever it is, when I commit, I show up."