Hollyweird Squares, Featuring Nikki Glaser, Ross Mathews, and More, Returns to the Stern Show

Celebrities appear alongside the likes of Wack Packers and porn stars as contestants try and win cash prizes

December 17, 2019
Six of the nine squares from Tuesday's Hollyweird Squares game Six of the nine squares from Tuesday’s Hollyweird Squares game Photo: The Howard Stern Show

Hollyweird Squares made its much anticipated return to the Stern Show on Tuesday and the celebrity and Wack Pack-filled segment turned out to be a contest for the ages.

Howard began by introducing the day’s contestants who both came to the show ready to share horrific holiday stories from their past. The first was Myk—pronounced like Mike—from Dallas who can boast an 144 I.Q. Unfortunately, Myk also shared how his heroin-addicted dad had left him and his 16-year-old mother when he was born.

“My mother was more the problem,” Myk told Howard, explaining she was an alcoholic who sent him off to the liquor store one Thanksgiving so she could do some swinging with his uncle.

Contestant Myk on the Stern Show Contestant Myk on the Stern Show Photo: The Howard Stern Show

The horror stories didn’t stop there. His mother apparently once also hooked up with his grandmother’s boyfriend, leading to an altercation during which his grandma shot his mom. Grandma then got arrested while Myk was put in a foster home.

The second Hollyweird Squares contestant was Josette, a woman who lived in a garage for two years after Hurricane Sandy destroyed her home. Her awful holiday story happened one Christmas while she was caring for her Alzheimer’s-afflicted father. After feeding him dinner she noticed diarrhea was spilling out of his adult diaper, so she took him into another room to clean him up, but while doing so he projectile pooped all over. “A little bit got in my mouth,” Josette explained, saying she recoiled so quickly when it happened she sent him flying into the Christmas tree.

“There was poop on the dog .There was poop everywhere,” Josette said.

Contestant Josette on the Stern Show Contestant Josette on the Stern Show Photo: The Howard Stern Show

Though Myk and Josette’s previous holiday experiences were unquestionably horrible, the future looked bright for the two Hollyweird Squares contestants who each had the chance to walk out of the studio with a nice cash prize.

“They’re ready to battle for big bucks, Robin,” Howard told his co-host.

Photo: The Howard Stern Show

Before getting started, Howard went square by square and introduced his special guests. On the top left was the indelible comedian and SiriusXM host Nikki Glaser. “I’m horrified,” she said after hearing Myk and Josette’s sad stories. Nikki also opened up a bit about the fallout from her September Stern Show appearance, revealing her mother had trouble tuning into the interview because she didn’t want to hear her daughter talking about oral sex.

Howard jokingly asked Nikki if being on Hollyweird Squares was one of her career highlights. “It truly is,” she replied. “I love these people.”

Photo: The Howard Stern Show

In the top right square was TV personality Ross Mathews, who told Howard he had broken up with his longtime boyfriend since his last time talking to Howard. He’s tried the dating apps since becoming single but so far it isn’t working out too well. “I got on Grindr and I got kicked off, Howard,” he said. “They said I was impersonating Ross Mathews.”

Ross was excited to be surrounded by such an interesting array of people on Hollyweird Squares, like InfoWars host “Alex Jones,” who was filling in for Sour Shoes. “I just bought my vitamins from Alex Jones. He said they can cure gay,” Ross laughed. He also said he had a surprise for the beloved Wack Packer sitting in the middle square, Wendy the Slow Adult—he’d brought her a bag of Sausage McMuffins and scratch off lottery tickets.

Photo: The Howard Stern Show

Wendy was excited to be back in the studio after spending 28 weeks in a rehabilitation facility recovering from an awful car accident. “I’m out but we’re waiting to hear from the therapy people if I can stand up and walk,” Wendy told Howard, adding she can go to the toilet on her own now but her mom still needs to help her wipe.

Wendy was flanked by two more Wack Packers in the middle row, High Register Sean on her right and Mark the Bagger on her left. Sean was excited to share the panel with fellow conspiracy theory enthusiast “Alex Jones” and during the introductions the Wack Packer was eager to talk about everything from 9/11 being an inside job to environmental activist Greta Thunberg being a time traveler. “It’s definitely possible,” Sean said. “There’s pictures of her from 1928.”

Mark, meanwhile, was eager to update Howard on his masturbation habits. He also chided one of the guests below him, former M.L.B. pro Lenny Dykstra, for dropped a ball during the 1993 World Series. Lenny, who also has a new podcast called “Pawning Nails,” didn’t have much interest in reliving his baseball career, but he did take a moment to try some sweet talk on every woman on the air that morning, including Robin.

Photo: The Howard Stern Show

Sharing the bottom row with Lenny was the porn star Jackhammer, wearing only underwear and socks, as well as Stern Show staffer Brent Hatley and his wife Katelyn. If the sexual tension felt palpable in bottom row it was because Jackhammer had bedded Katelyn in Brent’s home while the Stern Show was broadcasting from Los Angeles. As it turned out, though, Katelyn wasn’t the swinging Hatley who stepped out of line that week. She said it was Brent who “pretty much broke every rule” while the show was out West.

“When he got back I found out that he was basically trying to date every chick he hooked up with out there for like the whole week,” she explained on Tuesday.

“Brent why did you keep secrets?” Howard wondered.

“I was getting attention from chicks I don’t get attention from and I got carried away with it,” the staffer, who was dressed in heavy metal attire, admitted.

The game got underway with Myk selecting Wendy’s square. “If the President dies, who takes over?” Howard asked the Wack Packer.

“God,” she answered after a short pause.

Myk correctly guessed Wendy’s answer was wrong, so he got on the board first with “X” getting the center square.

Josette picked Nikki in the top left square with her first turn. Howard asked if it was true Japan celebrates National Hand Job Day on Dec. 25. “That is so absurd, I’m going to go true,” Nikki said.

“I disagree,” Josette said correctly.

“National Hand Job Day is celebrated every year on July 21,” Howard explained as “O” got the square.

Staying on the top row, Myk called on Ross with his next pick. “In 2013, Hallmark removed the word ‘gay’ from a Christmas ornament featuring lyrics from which popular holiday song?” Howard asked him.

“They removed gay. They had George Takei suck it out. That’s how they got it out,” Mathews laughed before guessing the song was called “Tis the Season.”

Howard called on Josette, who disagreed with Ross’s answer. She was correct—the song in question is “Deck the Halls.”

As Ross’s square was about to go to “O,” however, Stern Show staffer Jon Hein chimed in and revealed there had been a mix up. Myk was supposed to have guessed that one, so he was awarded the square.

Josette selected Lenny’s square with her real turn and the ballplayer turned sex aficionado was asked to give the scientific name for the vagina’s inner lips. “The labia cartas,” he guessed.

Josette strongly disagreed and, indeed, the answer was labia minora. “Like they use on Chanukah,” Howard joked as “O” got the square and blocked Myk from a quick win.

Myk picked Mark the Bagger next but before Howard could get the question out the Wack Packer began talking about sports and announced he’s looking for a woman.

“Where’d you put her?” Nikki joked.

Howard’s question for Mark was about the speed of male ejaculation, which may have been right up the Wack Packer’s alley considering his fondness for self-pleasure. Mark guessed it travels faster than 25 miles per hour.

Myk thought Mark was right and both men were correct. “X” got the square.

Josette selected another Wack Packer on her turn, High Register Sean. “Which U.S. state has the most reported U.F.O. sightings?” Howard asked the noted conspiracy theorist.

“I’d have to say because of their location between the continents it’s absolutely the state of Hawaii,” Sean answered.

“False,” Josette said. She was right, “O” got the square.

“Bullshit,” High Register said before asking Lenny whether he’d consider having sex with either a Sasquatch or a “dog person.”

“I have no idea what the fuck he’s talking about,” Lenny responded.

Myk turned to Brent and Katelyn’s square with his next pick and the Hatleys had to answer a true or false question about the percentage of open marriages which end in divorce. Brent believed the percentage was above 90 while Katelyn did not. They ultimately went with Brent’s hunch.

Myk correctly agreed—per CNN, 92 percent of open marriages end in divorce. “X” got the square.

Photo: The Howard Stern Show

Josette turned things over to “Alex Jones” with her next pick. “This year Starbucks received criticism for printing what phrase on their cups instead of ‘Merry Christmas’?” Howard asked the InfoWars host.

“Merry Holidays,” “Alex” guessed after taking a shot at George Soros.

Josette disagreed, she was right, and “O” got the square. “They wrote ‘Merry Coffee,’” Howard said. “Robin, are you tracking this game, did anyone win yet?”

The last question of the round was Jackhammer’s. Howard asked the porn star what present was given on Day 7 in the song “The 12 Days of Christmas.”

“Seven birds a-singing,” Jackhammer guessed.

Myk disagreed and he was right—the lyrics were “seven swans a-swimming.” Thus, “X” got the ninth and final square and Myk was declared the round’s winner, by a score of 5 to 4.

With no time for subsequent rounds, Howard benevolently sent both contestants home with the $2,000 prize. “Josette, Myk, I know you had some rough times in the past. I hope the money comes in handy. Thank you for playing the Hollyweird Squares,” he said. “To all our celebrities, thank you so much … we now wave adieu.”

“Don’t trust the government,” High Register Sean added just before the show went to a break.