As Dropout CEO and host Sam Reich says every episode, Game Changer is the only game show where the game changes every show, causing both the viewers and the contestants to not know what’s about to happen. That is, except for the July 28 episode “Who Wants to Be Jacob Wysocki?” (initially titled “Who Wants to Be… ?”). Only Jacob Wysocki was in the dark for his Who Wants to Be a Millionare-like episode that ended with the comedian, surrounded by some of his closest friends, receiving $100,000.
That episode is “something that I can’t really look at beyond the notion of accepting and enjoying it right now,” Wysocki tells Polygon. “It was an insane day that’s very difficult to articulate, and it’s a wild sensation to then have it be out and then everybody be like, ‘That’s tight.’”
“Who Wants to Be Jacob Wysocki?” was something of a mix-up for Game Changer. As Wysocki says, “The nature of these Game Changers are so mischievous and so rooted in ne’er-do-wellism.” Typically they involve some sort of mind games Reich plays on his contestants, like designing the episode “Yes or No” with the simple premise that the notoriously competitive Brennan Lee Mulligan could not win. Sometimes they get very heartfelt, like season 4’s “Don’t Cry” that celebrated Jess Ross, whose wedding was postponed and who recently hadn’t been able to walk for months after surgery. “Who Wants to Be Jacob Wysocki?” was similar to “Don’t Cry” in that it was a celebration of the Dropout alum who was going through his own hardships.
“I don’t talk about it too explicitly out in the open,” Wysocki says. “I lost my mom that year [2024] and pretty quickly after that, we lost a member of our sketch group, Roger Garcia the Third. There were just a lot of challenges surrounded with those two moments of grief, compiled with having to normally show up to work and deal with all of the things that a community deals with when they lose a friend, and the sort of copious amounts of tricky webs that get spun in grief.”
Viewers likely had no idea Wysocki was stuck in webs of grief. He was as jovial as ever during his first appearance on Game Changer earlier in the season, as well as during previous turns on Make Some Noise and Parlor Room. But Wysocki’s close friends knew, and they wanted to do what they could to help.
“All the flowers to Kurt Maloney,” Wysocki says of his “best bud,” who was instrumental in creating the episode. “He did a tremendous amount of great work and sourced things and pitched bits and formulated this and made it very special, with the help of Sam and the other Dropout team [members].”
The behind-the-scenes video, released one week after the Game Changer episode aired, revealed Maloney had been working with Reich since the beginning to help put “Who Wants to Be Jacob Wysocki?” together. However, it wasn’t easy for Maloney to keep the lid on it.
“There was a big moment where Kurt had to come up with a lie at a party,” Wysocki says. Maloney had let slip he had been talking to Reich about an upcoming project, and Wysocki felt it was a professional overstep to not include him in that conversation. “I was like, ‘It makes no sense that you’re having this sort of conversation with Sam without me being a part of it.’”
Wysocki was so miffed by Maloney’s faux pas that he called their mutual friends to explain the situation and ask, “Am I crazy that this is a professional overstep or like am I being too sensitive?” They all assured Wysocki the whole snafu was no big deal in an attempt to smooth things over and keep the episode a secret from Wysocki. In essence, they gaslit their buddy for his own good. “I took the L, you know, and then to be like, ‘Damn, I wasn’t wrong.’”
With the secret preserved until the day of taping, he had no idea what he was in for. “Before we started filming the episode, everybody did a really good job of keeping up the ruse that it was like this group-oriented situation,” Wysocki says, noting that he and fellow Game Changer participants Kimia Behpoornia, Jeremy Culhane, and Maloney were told everyone would get a turn. (At what? Who’s to say — it’s Game Changer!)
While filming the episode, it took Wysocki “a pretty decent amount of time” to realize it was going to be all about him. With the jib camera shots, lights and podiums, Wysocki easily figured out the game was an “interpersonal” Who Wants to Be a Millionaire, thinking, “I win a little bit of cash, I’ll get one wrong, and then somebody else will get a turn.”
His friends Tyler Cintra do Prado and Tyler Phillips (“The Two Tylers”) joining as part of a ripcord — the episode’s version of a lifeline — was the first sign that “there’s a little bit more orchestration going on here that I don’t think you’d be able to do for every single individual,” Wysocki says. When Scott Milton Brazee and Evan Rosenberg joined for a hot dog eating contest, Wysocki realized, “This is just me now, 100%.”
Still, at that moment, he wasn’t sure how much he could trust Reich. This is the host, after all, who sent his players, Wysocki included, to a party bus after wrapping “Sam Says 3” (the show’s mischievous version of Simon Says), only to then reveal the game wasn’t over and dock them points for their misbehavior on the bus. “I was like, is somebody gonna come and steal it all away? Is it fake? Is it real? Is there another corner we’re gonna turn and then all of a sudden we’re on a party bus again?” Of course, it was all real, and Wysocki was the only one playing catch up.
Fellow contestants Behpoornia and Culhane knew what was going on. They weren’t part of the development process, but “they were my emotional support friends,” Wysocki says. They flanked the comedian for most of the episode, once Reich called them and Maloney on stage to join the episode’s star.
One of the questions Wysocki had to answer was who he’d rank as the funniest of the group. He wasted no time in showering Behpoornia with praise, and just as quickly made Culhane the butt of the joke in ranking him last. It was a pattern I’ve noticed before. At the Dropout live improv show in Brooklyn earlier this year, Wysocki frequently heckled Culhane, calling him “Dumbo” more than once.
“There’s a lot of maturity and power in being able to be the heel,” Wysocki says. “[Culhane is] such a good comedian and such a mature comedian that he sees the value in an episode where somebody’s the bad guy or where somebody can be like shit on and made fun of. We all take turns being the dunce, and sometimes people just have a little bit of a bigger target to hit, you know.”
So many people played pivotal roles in making this episode happen, one of them being Wysocki’s father, Tim.
“One of the first people Kurt reached out to was my dad,” Wysocki says. “So my dad was aware of it for quite some time, and he was tight-lipped, man, he never let it slip.”
Wysocki asserts it wasn’t difficult for his father to keep the secret. “He watches what I do on Dropout because he’s a supportive father, but I don’t think he really understands, like, what it is and the nuance of online streaming and direct-to-consumer consumption.” The episode wouldn’t have been the same without the elder Wysocki’s surprise appearance at the end when his son is presented with the oversized check for $100,000.
Being awarded the money, surrounded by his friends, capped off an “insane day” for Wysocki. He said a few times during the episode how “crazy” it all felt, and that crazy feeling still persists almost a year later, but in a different form with the episode being released and available for Dropout’s nearly one million subscribers. “To see the episode be reverberated back to me through this notion of, like, all thumbs up. It’s pretty wild.”
Still, the reality of “Who Wants to Be Jacob Wysocki?” hasn’t quite settled in for the comedian. “I think there’s still a part of me that doesn’t even know if it’s real, you know. It’s that big of a gesture, and it’s that big of a sensation that I’ll probably be chewing on this for the rest of my life.”
