Hollyweird Squares 2022: Ike Barinholtz, Chris ‘Mad Dog’ Russo, and More Try to Help 2 Veterans Win a Cash Prize

Hollyweird Squares was back with a bang on Wednesday as an all-new batch of panelists visited the Stern Show to participate in an epic showdown between two military servicemen whose fates and fortunes relied upon guessing whether Wack Packers, celebrity superfans, and impersonators were as informed as they appeared.

Playing against each other were Mike from Texas and Shawn from Arizona, of the Navy and Army respectively. For the X’s, Mike, a petty officer who was awarded the Combat Action Ribbon, the Joint Service Achievement Medal, and the Navy Commendation Medal over 13 deployments, talked about being so proficient in hand-to-hand combat that he taught it to fellow service men and women. “You learn to fight with your rifle, you learn to fight with knives, or what we call weapons of opportunity — pick up a pipe, pick up a boot, whatever you have around you to eliminate the enemy,” he explained to Howard.

Mike appeared less proud of another distinction — with over 500 fake dating profiles, his face has been used to catfish people more than anyone else in the military. “It’s kind of getting old,” he admitted before adding, “There’s no medal for this.”

Representing the O’s, Shawn, a former Green Beret, maintained a competitive spirit against his fellow serviceman. “Navy SEALs are often better looking, but we can kick their asses,” he joked before recalling how he noticed his SEALs counterparts were treated much better when he attended a Special Forces medical training course. “Our instructor’s standing up and he’s going, ‘You pieces of shit haven’t earned anything’ … 20 feet over is the Navy SEAL formation and their guy’s up front and he’s going, ‘You are God’s gift to earth.’”

Filling out the squares and tasked with helping out the contestants was a wide variety of guests, including sports talk legend and recent Radio Hall of Fame inductee Chris “Mad Dog” Russo and actor and Stern Show superfan Ike Barinholtz. “I did get teary eyed … I got into it,” SiriusXM host Mad Dog told Howard of his induction before admitting he unexpectedly ad-libbed a 17-minute speech when he realized his fellow inductees were being verbose. “Everybody went too long, it took forever … [but] … I got three tables there, [they] flew from all over the country, what am I going to do, two minutes?”

Ike, who is an executive producer on the variety series “History of the World, Part II,” a sequel to the Mel Brooks’ 1981 film “History of the World, Part I,” talked about Brooks’ importance to the world of comedy. “I don’t think before him movies were really funny … before ‘Blazing Saddles’ it wasn’t like you’re laughing so hard you might soil yourself,” he remarked.

The actor was less impressed with frequent Stern Show caller Bobo, whom he tried to help in coming up with better questions earlier this year. “Like everything with Bobo, it did not work out the right way,” he explained.

Also on the panel were Howard Stern impersonator Matt Friend, Fake Liza Minnelli, Fake Kanye West, Fist Fest alum HungerrFF, caller Rooster, and Wack Packers Wendy and High Pitch Erik, the latter admitting to being quite taken with Ike. “It’s between Donnie [Wahlberg] and Ike Barinholtz now,” he revealed of his latest crush.

Let the Games Begin

The contestants wasted no time snatching X’s and O’s as Hollyweird Squares commenced. Panelists were quizzed about everything from song lyrics and notorious day spas to movie lines and questions about Tom Brady. Shawn won Round 1 by trusting that Fake Howard Stern had correctly identified the real Howard’s middle name (it’s Allan). In Round 2, however, the former Army green beret missed a question about porn genres and forfeited the deciding square to Mike.

With the servicemen tied 1 to 1, it was time for a third-and-final round!

Winner, Winner Diamond Dinner

The climactic battle boasted questions about Donnie Wahlberg and Mozart, and Mike was ultimately declared champion after correctly guessing Fake Kanye West was probably wrong about everything he said on today’s show.

“Boys, I thank you for your service,” Howard told his Hollyweird Squares contestants as he congratulated them, told them about their prizes — a $1,000 grand prize and $500 runner-up prize courtesy of Steven Singer — and thanked each of his panelists.

“It was great, and you represented your services well,” co-host Robin Quivers agreed.