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.

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.

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.

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."

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.

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.

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.

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).