The Most Awkward Moments From The Drew Barrymore Show

Audiences were slow to tune in to Drew Barrymore's syndicated talk show when it debuted in 2020. For two seasons, it garnered less than 750,000 pairs of eyeballs, roughly half of what Kelly Clarkson's daytime outing attracted, and not even a third of the numbers Ellen DeGeneres's show enjoyed.

While network viewers may have ignored the outing at first, the online crowd quickly embraced clips of the show via social media that fed them a diet of the Hollywood star's quirky, yet chaotic hosting style. By June 2023, those videos made "The Drew Barrymore Show" the most viral talk show around, boasting nearly seven billion minutes consumed by the masses, most of them via TikTok. Like imprinted ducklings, TV watchers eventually caught on, making Barrymore's talk show one of the fastest-growing afternoon offerings on air. 

Part of the attraction is most likely Barrymore's saccharine goofiness and a refusal to sweep her previous addiction and mental health issues under the rug. It's that candid demeanor that has made her relatable to younger audiences with problems of their own, providing the star with fodder to tackle those issues with a broader, mature perspective in front of the cameras. Sometimes, the results are profound. Other times, though, they make for uncomfortable television.

Drew Barrymore has been married three times – first to Jeremy Thomas in 1995, then to actor Tom Green in 2002, and finally Will Kopelman in 2016 — with only her third one lasting longer than a year. This track record compelled the "Charlie's Angels" star to declare she would never again walk down the aisle. "If you break up, you break up, it's not the world's biggest deal," she opened up on "The Drew Barrymore Show" in 2022. "But a divorce feels like such a ... I don't know, I don't think I can take it again." 

But she wasn't against rekindling with ex-husband Green on her program, which got a bit weird when Barrymore noted how the two were incommunicado nearly 15 years after their divorce. "A little backstory for anyone is that we haven't seen or spoken to each other in far too long," the host explained during the segment. Immediately, Green switched the topic by praising her on her show, as if trying to avoid the sensitive topic.

A few tear-jerking moments later, Green relaxed, saying, "It's nice to reconnect ... This is really the first time we've looked at each other face-to-face in 15 years." Neither revealed why they stopped talking all those years, although Green revealed that the trail simply went cold. "We are not in touch, really," he said on "The Alan Cox Show" long before his Barrymore appearance. "She's got her family now and stuff, so I'm really happy for her."

As Drew Barrymore's effervescent sidekick during the "Drew's News" segment of her talk show, Ross Mathews is notorious for putting his own fun stamp on the proceedings. As a broadcaster who cut his teeth on shows like "The Tonight Show with Jay Leno," "Chelsea Lately," and "RuPaul's Drag Race," Mathews is normally quite amiable with his host. But a few things Barrymore has said in front of the camera has stuck in his craw. High on that list was eating in bed, something that repulsed him when Barrymore casually told him about all the "bed picnics" she has had with her children.

"I don't judge if you eat in bed," noted Mathews during that exchange. "I'm just disgusted by it." He elaborated further. "I'm not a bed eater, I don't like it, it leads to crumbs which leads to gross," Mathews added (via Decider). "You know what I do in bed? I sleep. Why do you have to eat? You have a kitchen, you have a dining room. Why eat in bed?"

The two have disagreed on other subjects like texting a potential love interest after a date and whether couples should hash out their fights according to a schedule. During that episode, Barrymore suggested the two have monthly meetings to air their differences compiled in a notebook. "I'm gonna need another notebook," replied Mathews, jokingly holding up a tome already full of his own grievances.

One daytime TV scandal that had the Internet buzzing took place in 2020, when talk show host Ellen DeGeneres was exposed for not being as "kind" to her employees as her brand would suggest. That launched a series of Ellen-bashing among celebrities, and Drew Barrymore was no exception. But the former "E.T." child star was far more subtle when she prompted Dakota Johnson about one run-in with DeGeneres.

That awkward moment was teed up perfectly when the two started talking about their neighbors, at which point Johnson revealed that she lived next door to late-night talk show host Jimmy Kimmel and his wife Molly. "They're great neighbors. Except they have a lot of parties and they don't invite me," Johnson noted on the 2021 episode of "The Drew Barrymore Show." Barrymore coyly responded, "Is this for real? Because, you know, people have gotten in trouble for claiming not being invited to your party." Johnson gasped widely at the remark, only to burst out laughing when the host continued, "That was amazing, by the way." 

The exchange recalled Johnson's appearance on "The Ellen DeGeneres Show" a few years earlier when the host lamented about not being invited to her guest's 30th birthday party. "Actually, no, that's not the truth, Ellen, you were invited," responded Johnson, adding that DeGeneres gave her grief over not inviting her to her 29th birthday bash. Being put on the spot, DeGeneres later claimed she was out of town at the time.

Whenever Drew Barrymore plans something special to spike interest in her daytime talk show, she usually tries to avoid something that would be at the expense of a guest or the audience. But despite all precautions, one situation cropped up that they couldn't control. Late in 2022, one "Drew's News" segment had her and sidekick Ross Mathews debating on the topic of what you would do if your friends don't like your partner. After facilitating an audience poll on the subject, Barrymore heard a couple giggling in the bleachers and asked them what triggered the reaction. It turned out to have nothing to do with the topic, but still made for uncomfortable television. 

"You have to be honest and also not ruin everything, so it's difficult," said the male half of the couple. "You ruined everything," quipped his female other half. The long and short of the dispute involved the woman proposing to her man on the Brooklyn Bridge, which he quickly kiboshed and called "embarrassing." As the audience jeered the man during the segment, he quickly added that he wanted to propose to her but she had beaten him to the punch. "I wanted to do it myself," he said. "Later. But not today," as the audience erupted with laughter.

However, on social media, respondents were clearly on the woman's side. "She gagged him," said one viewer on X, formerly known as Twitter. "Her friends tried to tell her that man's afraid of commitment," quipped another.

"The Drew Barrymore Show" had to shut down in May 2023 when members of the Writers Guild of America went on strike. But that September, Barrymore announced that her daytime talk show would return. Although the show would have been compliant with WGA rules, she received heavy backlash from writers for not supporting the strikes. A week later, Barrymore backpedaled, stating the show wouldn't return until after the strike ended. 

"I have no words to express my deepest apologies to anyone I have hurt and, of course, to our incredible team," said Barrymore in a since-deleted Instagram entry (via Vanity Fair).  "We really tried to find our way forward, and I truly hope for a resolution for the entire industry very soon." But the damage was already done, as Barrymore lost a National Book Awards hosting gig because of her decision. She also upset her three head writers, who refused to rejoin the show when production eventually resumed after the strike ended.

What made for uncomfortable viewing, however, was the fact that once "The Drew Barrymore Show" returned to the air in mid-October, the first episode saw Barrymore make absolutely no mention of the WGA strike and the heartbreak involving her hasty decision to air the show when picket lines were active. Instead, audiences were treated to Barrymore interviewing Shania Twain, which took place on the singer's Nevada ranch. Critics blasted the show, including Variety, who called the return episodes "meandering muddle."

Mitigating the weird and wacky goings-on during "The Drew Barrymore Show" is the host's consistent mission to keep things casual, even if it involves kicking off the heels and kneeling on the couch while interviewing a guest. Then there are other times when she gets a bit too casual for her audience and abandons the furniture altogether to hold court on the floor, as if she developed an allergy to the cushy fixtures adorning the set.

During one interview with TikTok personality Dylan Mulvaney, she defended her decision on where to plant her butt. "Thank you for joining me on the floor," she said to her guest. "The floor always feels safer." When quizzed about her penchant for a ground-level interviewing style as a guest on "The Tonight Show with Jimmy Fallon," Barrymore responded, "I feel this magnetic pull."

A collection of fan responses by Parade revealed that audiences were either deeply confused or put off by Barrymore's personal floor show. "The show should be named Drew getting on the floor every episode," noted one viewer on X. "Why does she keep doing this on the floor thing. I find it strange lol," added another. Another Barrymore fan echoed similar sentiments on Instagram, saying, "I like Drew but she needs to stop crawling on the floor."

What part of the ground Drew Barrymore chooses to park herself hasn't been the only bone of contention to those who watch her daytime talk show. They've also raised a stink about how she interacts with her guests during interviews, from extensive hugging and touchy-feely gestures to venturing into more TMI tidbits about her personal life. One observer on Reddit noticed that Barrymore seemed to invade guest Pamela Anderson's physical comfort zone when the "Baywatch" star appeared on the show. "I love Drew's interview with Pam Anderson but look at their body language during it," noted the contributor. "Drew is sitting close, facing Pam and leaning forward, Pam sits angled away from her leaning back. It seems like Pam would have preferred more space." 

Conversely, some guests on the show get into sharing space, like actor Kathryn Hahn, who dug the notion of sharing their grooming processes when Barrymore showed off her recently shaved legs. "It's a good thing I just happened to shave my legs," said Barrymore while showing off her tattooed limb. Eagerly answered Hahn, "We can compare! I definitely have not!"

As overly intimate as her approach might seem, Barrymore defended herself on "The Tonight Show with Jimmy Fallon," saying she's merely trying to make her guests feel comfortable with her and put "good energy in the room." As innocent as her intentions are, the up-close-and-personal interviewing style definitely turns off some viewers.

Relationships are frequently discussed on Drew Barrymore's talk show, and she has tried to explore every avenue, including the nerve-wracking blind date. She previously set people up among audience members during the show, and during one Valentine's Day episode had three potential couples take part in pre-recorded, sequestered dates, but never had anyone go through the ritual in front of a live audience.

That is, until a 2023 episode, when Barrymore enlisted the help of dating pundit Damona Hoffman to coach a young woman named Bernice to go through a whole first date in a coffee house setting onstage. Once the date was underway with a man named Alton, Barrymore briefed the audience on what was happening. "Damona and I are going to help Bernice through anything that we see fit or see if we can jump in and be her wingman," she said from the sidelines while the daters sat awkwardly waiting for the live segment to begin.

Thankfully, the audience remained quiet while watching Bernice stumble through the date, which clocked in at around five minutes. When it looked like she'd falter during the exchange, Barrymore and Hoffman would hold up cue cards behind Alton encouraging Bernice to do things like test her flirting skills and just be herself. As uncomfortable as the situation was for viewers, something must have worked, as Bernice finalized a second date with Alton.

Although Drew Barrymore has prided herself in avoiding the "gotcha" style of journalism for which other shows are infamous, she's not above pulling a fast one on her guests. Enter actor Julia Fox, who agreed to do Barrymore's makeup during their interview, where they talked about the ideal man to date, career hard knocks, and news that her guest was working on a fashion show.

Upon hearing the news of Fox's own program, Barrymore suddenly sprang up from the couch and ran off the stage, leaving a very bewildered Fox on her own. "Oh, wait, wait, where's she going?" asked Fox to no one in particular. "Is this normal? Does she always do this?" Quickly laughing and collecting herself, Fox addressed the audience, with, "So, anyway, welcome to my segment. I'm taking over for her."

After a commercial break, Barrymore reappeared in Fox apparel, complete with a set of Marc Jacob boots and a giant, chain-link necklace. "Wow, you look amazing," marveled Fox over the fashion statement Barrymore was able to pull off. But Barrymore wasn't done with her yet, showing a social media video shot by Fox depicting her messy bedroom and bathroom, while gushing over how such a glamorous personality could remain grounded in her daily life. "The majority of my life is just very regular," answered Fox.

Given that the duration of two of Drew Barrymore's marriages being roughly one year, it's probably no surprise that the "50 First Dates" star is reticent about walking down the aisle again. During one 2023 episode, Barrymore remarked to one of her guests that was dealing with post-divorce dating, "We have something in common, which is, I will never get married again."

That comment probably resonated among Barrymore's following when one unusual suitor appeared on her program in 2023. Comedic actor Pauly Shore, best known for starring in movies like "Encino Man" and being a recipient of worst-actor Razzies for his work in "Jury Duty" and "Bio-Dome," showed up to pop the question. During their interview, Shore revealed that his mother, the late comedian Mitzi Shore, wasn't crazy about Drew's short-lived coupling with Tom Green. He suggested that his mother felt her son would have been a better partner.

"That's how Mitzi felt?" exclaimed Barrymore. "No, that's how I feel, too," he laughed as the audience tittered. "And that's why I came here tonight on this glorious night to present you with a ring." At that point he knelt and produced a rock the size of a small sink plug. For some viewers, the moment was creepy, given that Shore used to babysit Barrymore when she was much younger. The fact that Barrymore never produced an answer to her proposal also suggested that the whole thing was a gag anyway.