Dr. Phil's Most Uncomfortable Celebrity Interviews

This article includes references to addiction.

Dr. Phil McGraw first shot onto the scene in 1998 when he appeared on an episode of "The Oprah Winfrey Show" on the eve of Oprah Winfrey's win in her trial with the Texas beef industry. McGraw was a consultant during the trial, and his appearance led to another two years later — which then led to his own show the following year. 

"Dr. Phil" began in September 2002 and ran until May 2023, pumping out more than 4,500 episodes along the way. McGraw has since moved into podcasting, where he has established himself with multiple programs including "Phil in the Blanks" and "Mystery and Murder: Analysis by Dr. Phil." While he has moved away from the more tabloid-style content he was doing on TV, McGraw remains a controversial figure for a number of reasons.

One issue people have with McGraw, who has a doctorate in psychology, is the fact that he practices therapy despite not having an active license to do so since 2006. Furthermore, many of his featured guests had no business being on television, and many feel that the show exploited those who had real issues for the show's commercial gain. Some audience members took such issue with McGraw's practices (and problematic comments) that calls for his cancellation were around long before CBS actually pulled the plug on his TV show. Even though "Dr. Phil" focused mostly on normies, McGraw scored a fair number of celebrity interviews over the years, many of which were incredibly cringy. Here are Dr. Phil's most uncomfortable celebrity interviews.

As far as "Real Housewives" go, Kim Richards is a fan favorite who lit up the screen during the early years of "The Real Housewives of Beverly Hills." The former child star is both lovable and a bit kooky, which would make her a perfect reality star if a fair amount of that zaniness were not due to substances. 

Richards' alcohol issues were at times documented on "RHOBH," but there was still a lot that was left out of the story. Take, for example, her arrest for shoplifting $600 worth of goods from a Target store in Van Nuys, California, or her arrest at a hotel on three misdemeanors after a drunken outburst at a hotel months earlier. Both occurred in 2015 but were hardly discussed on "RHOBH," despite Richards still being on the show at that point.

Richards opened up about her legal issues when she sat down for a "Dr. Phil" interview in April 2015, so she was not hiding anything per se. Still, there is a big question mark in terms of how truthful she was, since she admitted to previously having lied about being sober on Season 5 of her reality show. Richards' "Dr. Phil" appearance is one of Phil McGraw's most memorable celebrity interviews, as it also included an attempt on McGraw's part to get Richards into a Malibu rehab. The reality star accused McGraw of trying to stage an intervention and walked off the set. As truly uncomfortable as it was, it was effective — Richards checked into rehab only days later.

Nick Gordon was not a celebrity in his own right, but he became one because of his close association with famous folks. Gordon was the boyfriend of Bobbi Kristina Brown, the only daughter of Whitney Houston and Bobby Brown (Brown has six other kids from various relationships). Gordon was with Bobbi Kristina when she died at the young age of 22, and since that evening brought forth many questions, Gordon was the subject of much speculation and scrutiny. 

Both Gordon and his girlfriend were under the influence when she passed out in a bathtub in January 2015, later dying after six months in a coma. Though no criminal charges were ever filed, Gordon was found responsible in a civil suit and ordered to pay $36 million to Bobbi Kristina's estate. Tragically, Gordon also died young — passing away at age 30 in 2020 from a heroin overdose.

Gordon appeared on "Dr. Phil" two times, once in 2015 and then for a two-part special in 2016. While the second appearance was no picnic, it was the first of these appearances that was truly discomforting. The episode was filmed in March 2015, fresh off the accident, and Gordon was admittedly under the influence of drugs and alcohol. The interview turned into an intervention, and Gordon even threatened suicide during the heart-wrenching "Dr. Phil" episode. "My pain is horrible," he wailed through tears. "Like, my heart hurts. I have panic attacks." Gordon went to rehab after the provocative episode and then returned to "Dr. Phil" in late April.

Some of the "Dr. Phil" interviews on this list were simply awkward, while others were straight-up problematic. Phil McGraw's 2016 interview with actor Shelley Duvall falls into the latter category, and unsurprisingly, McGraw and Duvall differ in their feelings about the controversial talk show episode. Duvall was a working actor for more than three decades, and she is best known for her work as Wendy Torrance in the 1980 horror classic "The Shining" and for starring as Olive Oyl in "Popeye" — although her work in the film "3 Women" made a splash on the awards circuit a few years before that, putting her on the map. Duvall had long been out of the public eye when she appeared on "Dr. Phil, in an episode where she revealed her struggle with mental illness.

During the uncomfortable interview, Duvall claimed that Robin Williams was still alive (he died in 2014) and that he was a shapeshifter. This was just one moment where Duvall's illness was clearly presented, and viewers were outraged at the exploitative nature of the interview. Though McGraw has said he does not regret the interview — copping only to regretting "that it was promoted in a way that people found unbecoming" — Duvall clearly does. "I found out the kind of person he is the hard way," she told The Hollywood Reporter. Likely wanting to quiet the backlash and/or further exploit the actor, McGraw kept hounding Duvall to make another appearance. He even pestered her mother with calls, but Duvall wisely stayed clear of "Dr. Phil" after that questionable appearance.

The guys of "Jackass" have spent decades engaging in dangerous stunts, gross pranks, and plain old debauchery, but somehow, most of them are doing alright and even have their limbs intact (Ryan Dunn, who died in a car crash in 2011, notwithstanding). While the "Jackass" crew has displayed perseverance, there have been plenty of problems since the franchise first took off with their MTV show in 2000. This includes issues with substances, mental health, and the law — and that is just Bam Margera. Brandon "Bam" Margera has been arrested numerous times, including in August 2023 (for public intoxication and disorderly conduct) and in April 2023 (after an altercation with a family member). It is obvious he has yet to hit rock bottom, despite appearing on "Dr. Phil" years ago pleading for help.

Margera was on "Dr. Phil" in 2019, and the appearance was quite rough. Amongst other things, he talked about having a mental breakdown and of contemplating suicide — things that are all the more devastating considering he was involuntarily committed as recently as June 2023 for suicidal threats. It was also awkward watching Margera tell his wife to leave him alone, while at the same time admitting that he might hurt himself if she did give him space. Margera literally cried out for help, and he went to rehab after the show, but he continues to struggle. He completed a one-year in-patient rehabilitation program in 2022, but even that was not enough to turn things around for the troubled star.

As the parent of an actor, Dina Lohan should not be a celebrity, but she has certainly maneuvered her way into the spotlight enough times that most people would consider her one. Though she lacks her famous daughter Lindsay's talent, the controversial stage mom loves the camera, and nobody was surprised when she decided to go on "Dr. Phil" in 2012. In the interview, Phil McGraw focused largely on Lohan's reputation and suggested poor parenting — even reading media headlines dubbing Dina the "worst mother in America" and "worst parent ever." This was uncomfortable in itself, but it was just the tip of the iceberg when it came to the interview's awkward moments.

Lohan took very little accountability for her behavior, and often dodged questions about her parenting and her daughters' legal troubles by asking if the cameras were rolling or making comments about lighting. "We're probably going to be done here in just a very few minutes, so let's at least have a few minutes of authenticity," an exasperated McGraw stated. "You deflect everything." McGraw was not wrong, but people were much more interested in Lohan's demeanor than her deflection. 

Many agreed with Lohan's ex, who suggested (via satellite) that she was under the influence. Although Lohan herself denied being drunk, media coverage focused on how Lohan slurred her words, hurled her limbs, and had no ability to focus during the odd interview. Sober or not, the erratic "Dr. Phil" appearance did little to change the poor public perception of Lohan or her brood.

Nicholas Brendon at one point had a promising Hollywood career, but the actor had fallen from the high of "Buffy the Vampire Slayer" by the time he first stepped onto Phil McGraw's set in September 2015. By that point, the star — who has also appeared in "Criminal Minds" and "Private Practice" — had been to rehab a couple of times, beginning in 2004, and had been arrested for vandalism, resisting arrest, battering a police officer, grand theft, criminal mischief, and more. Brendon's "Dr. Phil" appearance came fresh off the heels of a June rehab stint, which was preceded by three separate arrests in the early part of 2015. The star was certainly in need of therapy, but it probably did not need to happen on television.

The initial "Dr. Phil" interview was so tense — at one point, McGraw noted alcohol on Brendon's breath — that the actor angrily stormed out of the taping. He was particularly offended that McGraw critiqued his mother for how she handled his childhood sexual abuse. "Dr. Phil had some hard words for my mother, who I love dearly and who I have caused more heartache than I care to remember," Brendon wrote on Facebook (via People). Brendon was again arrested that October and returned to "Dr. Phil" in December after 90 days in a treatment center for depression. His second appearance was gut-wrenching, as the actor provided details about his abuse and his past suicide attempts. Sadly, Brendon has been arrested numerous times in the years since, including for domestic violence and fraud.

The word "uncomfortable" could be used to describe plenty of things related to June Shannon and her family, since their time in the public eye has been marred by controversy and even their show featured plenty of odd, gross, or plain befuddling moments. But when Shannon (a.k.a. "Mama June") appeared on "Dr. Phil" in 2014, it took uncomfortable to a whole new level. Shannon's appearance was scheduled so that she could speak about a recent scandal that got her family's show "Here Comes Honey Boo Boo" canceled by TLC. The show was cut due to Shannon's romantic involvement with an ex — a convicted sex offender who went to jail for molesting Shannon's oldest daughter Anna.

People understandably lost it when Shannon was photographed with her ex and her youngest daughter Alana "Honey Boo Boo" Thompson, so the "Dr. Phil" interview was an opportunity for Shannon to take accountability for her poor judgment and express regret. In the interview, Phil McGraw gave Shannon an opportunity to admit to her mistakes, but she sat there stone-faced as he went on and on about owning up to one's decisions. She also lied about various things, including when she found out about Anna's abuse and about bringing her boyfriend around her kids. "I told her I did not believe what she had to say. She just simply is unwilling to tell the truth," McGraw later told TMZ. "This woman has been making really bad choices with these children and with the men in her life for a long, long time."

Plenty of guests, celebrities included, have expressed regret about appearing on "Dr. Phil." A few of them have even stormed off the set, clearly making their displeasure known through such drastic action. But most of these people have waited until after the show to start bashing Phil McGraw and his TV series, if only because of how awkward it would be to do it while sitting up on stage with the uncredentialed doctor. 

"Teen Mom" star Farrah Abraham walks to the beat of her own drum, however, and she had no problem making things super uncomfortable by telling McGraw on the air how much she regretted being there. Considering the things Abraham has done since she became famous — including her very cringy sex tape, her DUI, selling her poop on OnlyFans, and posting racy TikTok videos with her young daughter — going on "Dr. Phil" seems like it should be low on the list of regrets.

Abraham visited Phil McGraw's talk show in April 2013, by which time she had already appeared on MTV for four seasons. She has somehow been able to keep booking TV gigs — everything from "Couples Therapy" to "Ex on the Beach" to "Celebrity Big Brother" — despite being a deeply controversial and not super well-liked reality star. Add McGraw to the list of people who are not on Team Farrah, since his stance was clear during the entire interview. "You have an incredible sense of entitlement, and when you don't get your way, you get upset," he told the pouting star (via TODAY).

It was virtually impossible to watch Orlando Brown's "Dr. Phil" interview and not be taken aback by the oddities at hand. For starters, the former child actor wore super creepy snake eye contacts on the show, which he said was a Halloween-themed joke. He also claimed the eyes were "Michael Jackson's eyelids from Thriller," which would have been weird enough without the rest of the interview. But Brown also said Jackson was his father at one point, claiming that his full name was "Orlando Brown Prince Michael Jackson Jr." and suggesting he was Jackson's younger son known as Blanket. Brown was very obviously unwell during the interview, but he also got offended when Phil McGraw offered him help.

It was all tough to watch, and it is even sadder looking back on the interview knowing that Brown continues to struggle. The "That's So Raven" star was arrested for domestic violence in December 2022, and a few months later, was ordered to undergo a mental evaluation. This all came four years after Brown's memorable "Dr. Phil" interview, which was staged like an intervention and included claims from Brown's friends that he was homeless, addicted, and mentally unwell. Brown — who had already been arrested many times that year — got tripped up on the simplest of questions, including the names and ages of his kids, and McGraw had to explain to him how the inconsistencies did not make sense. Brown even claimed that his two-year-old was "still in the belly," further proving his weak grasp on reality.

The Carter family has suffered immeasurable loss over the years, but if anything, we know too much about the clan's struggles and dramas. The family's intense desire for fame and the cash flow that came with Nick's (and later Aaron's) success seem to have only exacerbated existing issues, leading the Carter fam down a path of dysfunction. Two of the five siblings (Aaron and Leslie) have died due to their substance use, and both of them suffered from poorly treated mental illness. Even the family's biggest name, Nick, has struggled with addiction, not to mention his legal issues and the allegations of sexual assault from multiple women. The Carter family story reads much like the families frequently featured on daytime talk shows, except with money and fame thrown into the mix.

Nick Carter sat down for an interview with "Dr. Phil" in 2013, one year after Leslie overdosed. Since he was there to promote his memoir, "Facing The Music And Living To Talk About It," the Backstreet Boy spent a good deal of the interview discussing his own addiction and his tumultuous family dynamic. He also talked about his sister Leslie, admitting that his family blamed him for her death since he had stopped talking to her prior to her overdose (of note, Nick sadly was also estranged from Aaron when he drowned in the tub a decade later). The most discomforting part of the interview was when Nick confessed that he neglected to attend Leslie's funeral because of the toxicity between him and his father.

Dr. Phil McGraw has booked a fair number of talented celebrities for interviews over the years, including the late singer Sinead O'Connor and "The Partridge Family" actor David Cassidy, both of whom touched on difficult topics like addiction and health when they sat down with the TV doctor. But actors and singers are disproportionately outnumbered by reality stars when it comes to McGraw's celebrity interview list, and that is unsurprising considering the way that most reality television stars thirst for attention, even if it is negative. Sometimes, you even get a reality star's daughter, which is what happened when Lindsie Chrisley popped in to talk about her currently incarcerated parents Todd and Julie, stars of "Chrisley Knows Best."

Chrisley was featured on her family's reality series but in a much smaller capacity than her younger siblings. This is likely because she is older and was not living at home, but also perhaps because she does not share the same mother as them and has a very toxic relationship with her father. That toxicity was on full display when Chrisley made her 2019 "Dr. Phil" appearance, and it was tough to watch. During the interview, Chrisley claimed that her father accused her of having an affair with a tax official (the Chrisleys are in jail for tax evasion and fraud) and threatened her with the release of nude photos and a sex tape that her brother allegedly purchased (ick). Though Todd denied the claims, it is hard to take a convicted felon at their word.

In the vast majority of cases, it is Dr. Phil McGraw who makes his interviews uncomfortable, either by putting people on television who probably require much more private interventions or by the things that he says to them when they are face-to-face. And, sure, he had a hand in making actor Eric Roberts' interview super awkward, but the main reason it is on this list is because of Roberts' wife, Eliza. Of course, she was only noting the curt way Roberts responded to a question McGraw should never have asked, so all roads do lead back to the mustached talk show host.

Roberts appeared on "Dr. Phil" in 2012, one year after appearing on "Celebrity Rehab With Dr. Drew." The Academy Award-nominated actor was there to discuss his addiction and the way it had impacted his life, including his family and career, which he hoped to get back on track. It went fine, for the most part, but Roberts was clearly annoyed when McGraw decided to ask about his sister and daughter (Julia and Emma Roberts, respectively). While he did not go off on the host, Roberts responded in a very direct way that made it clear that McGraw was aware both women were off-limits topics prior to filming. So, that was awkward to begin with, but the situation became even more cringy once Roberts' wife called him out for his "testiness" toward McGraw. It was about as comfortable as watching a passive-aggressive couple fight at a dinner party.

If Levi Johnston's name is not familiar, just think back to 2008, when John McCain chose Sarah Palin as his vice-presidential running mate. The years that followed were a total clown show, but they made pretty much everyone in the Palin clan a household name. Aside from Sarah, oldest daughter Bristol was the most talked about Palin, largely because she was an unmarried and pregnant teenager. Bristol later had her own Lifetime reality series, appeared on "Dancing With the Stars," and joined the cast of "Teen Mom OG" (for a season). Wrapped up in all of this was Johnston, Bristol's former fiancé and the father of her eldest child, Tripp.

As an unofficial member of the Palin family, Johnston was also able to get his 15 minutes of fame. He wrote a book, tried his hand at acting and modeling, and even had a fake little romance with comedian Kathy Griffin (documented on an episode of her reality show). Heck, the guy even posed for Playgirl, so no one raised an eyebrow when he went on "Dr. Phil" for a tell-all interview. The 2011 interview was predictably messy, but the part that was truly gross was when he discussed Bristol's virginity, which he did in response to claims Bristol made in her book. We get that Johnston wanted to defend himself since Bristol said she was so drunk that she felt Johnston "stole" her virginity, but it was still icky watching him talk about it on national television.

Unlike all of the other interviews on this list, Donny Osmond's sit-down with Dr. Phil McGraw was not awkward because of the interactions between the host and guest or the sensitive nature of the subjects at hand. No, Osmond's interview was uncomfortable because he essentially turned it into an advertisement for a product he was representing. It was not the only instance of Osmond hijacking an interview to pitch the product — he also did it on "The Morning Blend," for example — but it was especially out of place on "Dr. Phil." It was also about as subtle as a sledgehammer.

Osmond has been a celebrity since he was a child, so he knows how to do an interview. He also knows how to sell a product, even if it is something as random as Protandim, a dietary supplement from LifeVantage. The singer had already been a spokesperson for the brand for half a year by the time he appeared on "Dr. Phil" in February 2012, and the logline was that he had started taking the supplement at the suggestion of his doctor. 

There is nothing wrong with stars representing products, but the lack of transparency in the "Dr. Phil" interview was insulting to the viewers' intelligence. McGraw launched into a speech about how busy Osmond was and asked him where he got his "energy" from, as if he did not know full well the ad that was about to happen. They then launched into Osmond's "secret," using cliched phrases like "fountain of youth."

Gary Busey just being himself is often off-the-wall, so when you throw him into the hands of a psychologist-turned-tabloid-talk-show-host, you know you are in for a certain level of chaos. Busey's appearance on "Dr. Phil" was far from his oddest interview ever, but that bar is incredibly high and even the actor's tamer interviews are filled with uncomfortable moments. 

Busey appeared on the show in October 2018, as part of the press tour for his autobiography, "Buseyisms: Gary Busey's Basic Instructions Before Leaving Earth," which had come out the month prior. The episode saw Busey discussing his drug addiction and a near-fatal overdose, as well as his career and a devastating motorcycle accident that left him with a traumatic brain injury (his doctor also showed up for that part).

It is always weird to see a celebrity's doctor pop into an interview to tell the world about their patient's diagnosis (unless perhaps there is a larger purpose such as spreading awareness about a lesser-known issue). This instance was more like we were inside Busey's medical appointment, which would have been enough to land the interview on our list if the actor was not also so zany. Amongst other things, Busey discussed snorting drugs off of his dog during the interview. His exaggerated facial expressions, his eccentric mannerisms, his tendency to get out of his seat or make weird noises, his out-there stories — all of it was like a car crash from which you could not peel your eyes away.

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).