Gaming and esports influencers and executives dish on their most dreaded video game bosses

esports gamers

As executives flow in from the media, entertainment and sports sectors, the proportion of genuine, dyed-in-the-wool gamers occupying leadership positions at gaming and esports companies declined in recent years. Influencers are gaming less, too, with popular streamers such as Ludwig Ahgren spending less time simply playing in front of an audience in favor of MrBeast-style content creation.

Still, gamers form the nucleus of the gaming and esports community, and bona fide gamers are still very present at all levels of the industry. In gaming and esports marketing, authenticity is key, and lifelong gamers understand the community better than anyone.

As shown by the success of Elden Ring this year, challenging, narrative-based titles are still ideal for many core gamers. Digiday reached out to 17 prominent executives and influencers in the gaming and esports industry to ask about their most dreaded video game boss — and why.

Here’s what they said:

Activision Blizzard vp of global business research and marketing (and author) Jonathan Stringfield:

“A riddle: What do you call it when you are stuck in a tiny room with a giant bug who can almost instantly squash you? Answer: A health potion chugging competition, which is indeed the only viable strategy for fighting Duriel, a Diablo 2 boss that was inflicted upon us all once again with Diablo 2 Resurrected. The fact that Duriel is the ‘Lord of Pain’ seems fitting, as he is by far the most painful part of the game — I’d rather go toe-to-toe with Diablo himself.”

Annie Scott Riley, CMO of esports company Version1:

“I am still mad at Rennala, Queen of the Full Moon in Elden Ring. In her first phase, before you can damage her, you have to attack these army-crawling, occasionally levitating ‘scholars’ who are chucking books at you. This isn’t particularly difficult once you understand the warning signs for falling chandeliers — chaotic much? Then, in her second phase, you’re transported to this moonlit, magical realm. It’s distractingly majestic, and her spells are crazy; she summons shadows of other bosses to gang up on you.

“I’ll be honest, I couldn’t solo her at all, but with the help of a kind stranger to divert her attention, I was finally able to take her out. Unfortunately, a millisecond later, I was hit by her final sorcery, which meant I absorbed her runes and then died — in the realm of the second phase. Which can never, ever be accessed again. So I won, but I lost everything I came in with, plus whatever I would have earned. Nightmare fuel. Miyazaki is a magnificent madman.”

Twitch streamer and YouTuber Hannahxxrose:

“My most dreaded video game boss is definitely the Ender Dragon in Minecraft. It’s super daunting to fight and is a big risk to lose your loot, especially if you’re speedrunning the game. Despite me playing the game for 8 years now, I’ve only ever defeated it once — and I needed help from some friends!”

Josh “Caru” Glodoveza, VP of talent at Fanjoy:

“For me, it’s the Wall of Flesh from Terraria. Imagine a literal wall of flesh with multiple bloodshot eyes, and eyes with a mouth and sharp teeth. It spawns in the underground and will chase you till the very end of the game’s map, until there is no room left to escape. I feel it’s a great metaphor for life, about being put into corners and bealaning forced to make do with the situation you are in. Although it’s the final boss before the game goes into Hardcore and opens a whole array of even harder challenges. To me, that sounds like going into adulthood. I can face some of the biggest challenges right now, but it doesn’t mean they will stop coming, and I just have to adapt and take it day by day.”

Brian “Saintt” Baroska, head coach of the Call of Duty League’s Minnesota Røkkr:

“One of the hardest bosses I’ve ever faced was the optional boss Sigrun in the most recent God of War game. That boss gave me so much trouble to the point that I lowered my game difficulty from hard mode all the way down to easy after dying 100-plus times.”

Twitch streamer and Evil Geniuses team member ARUUU:

“I think my most dreaded boss of all time is Lady Yunalesca from Final Fantasy X. I often wonder if it’s because I was a child when I played the game, or if it really was just that difficult. I remember crying to my brother to beat it for me, because I had been stuck on it for days. Overall, though, she’s pretty difficult, and felt nearly impossible to beat. Even my brother was getting frustrated and annoyed with it.”

Mark Flood, director of North American operations at Astralis:

“Literally any Elden Ring boss, because I never beat any of them.”

(As a follow-up:) “F Elden Ring.”

Michael Ashford, CEO of the Esports Awards:

“Whitney’s Miltank [from Pokémon Gold and Silver] still gives me nightmares from my childhood; the impending doom as Rollout continued to work its way through my under-prepared team taught me some valuable life lessons.” (Disclosure: This boss is this Digiday reporter’s pick, too.)

Washington Post games reporter Gene Park:

“It’s Sword Saint Isshin, the final boss of Sekiro. I spent almost an entire week trying to beat him, an experience so draining that it almost turned my feelings on the game inside out. I don’t want to revisit Sekiro now that I know he’s waiting. I just couldn’t get the timing perfect enough for as long as the fight demanded. It’s not a fight I want to experience again, and I’ve only played Sekiro once more since.”

Paul Mascali, head of esports and gaming at PepsiCo:

“Personally, my most dreaded boss would be Jack of Blades from Fable. I always struggled with the second phase of that boss fight. Took me hours to finally beat it!”

Cory Vincent, vp of integrated solutions at NRG:

“For me personally, Mike Tyson’s Punch-Out!! was the original Dark Souls. No matter how young I was, or how old I get, I just don’t think I’ll ever have the skills or reflexes to beat him.”

Steven Salz, CEO and co-founder of Rivalry:

“Back in the vanilla World of Warcraft days, it would be Onyxia for sure. This is the first years of WoW, where only one or two guilds had cleared it in the server. The Ventrilo coordination days. I’d say it was dreaded because it was complex to get a 40-person raid to do everything they were supposed to do, and it would reset for a week if you failed. Everyone wanted the drops, so just the anxiety of winning the roll as well if your class item dropped. Just a stress-fest.”

Twitch streamer (and 2K NextMakers mentor) Mitsu:

“Most dreaded in-game boss? Half-Life’s last boss, The Nihilanth. An imposing and challenging last boss, capable of teleporting you to dangerous side rooms, summoning powerful floating enemies, and having a very difficult to access weak spot — there is no more fitting a last boss after traversing the already notoriously difficult world of Xen.”

John Jung, vp of operations and studio at Evil Geniuses:

“Literally every boss in Witcher 3 terrified me. I could not play this game at night.”

Gil Hirsch, CEO and co-founder of StreamElements:

“After hitting all the combos at Horizon Forbidden West’s Training Pits, The Enduring reminded me what a great boss fight was all about: an endless loop of taking a beating, incremental improvements, false hopes, setbacks, repeat. Until you land that final blow, thrilled and exhausted.”

Joshua Brill, head of marketing at Fnatic:

“To be completely honest, the final Doctor Neo Cortex boss scene [in Crash Bandicoot] wasn’t the hardest — evading the voodoo mask spirits Aku Aku and Uka Uka by jumping around and eventually spinning Doctor Neo Cortex down a wormhole — but it still sticks in my mind as a final boss that made me sweat a lot at 10 years old. The climatic metal music will always make it timeless for me!”

Andrei Van Roon, head of League Studios at Riot Games:

“While it doesn’t seem so hard in hindsight, the Gargoyles fight in the original Dark Souls absolutely demolished me at the time. I went into the game blind, and while I loved it, I had no idea what I was doing. I was under-leveled, hadn’t upgraded equipment, was heavily overloaded, didn’t understand how parrying worked and didn’t want to summon help. It took me an incredibly long time to get through that fight as a result, though the lessons painfully learned did make most of the rest of the game seem easy by comparison!”

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