Gaming and esports influencers and executives share their most feared video game bosses

As executives flock from the media, entertainment and sports sectors, the proportion of true, seasoned gamers holding leadership positions in gaming and esports companies has declined in recent years. Influencers are also gaming less, with popular streamers like Ludwig Ahgren spending less time playing in front of an audience in favor of creating MrBeast-style content.

Still, gamers are at the heart of the gaming and esports community, and bona fide gamers are still very much present at all levels of the industry. In gaming and esports marketing, authenticity is key, and lifelong gamers understand the community like no other.

As shown by the success of Elden Ring this year, challenging story-based titles are still ideal for many core gamers. Digiday reached out to 14 prominent executives and influencers in the gaming and esports industries to ask about their most feared video game boss — and why.

This is what they said:

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

A riddle: What do you call it when you’re stuck in a small room with a giant bug that can crush you almost instantly? Answer: A competition to slurp health potions, which is indeed the only viable strategy to fight Duriel, a Diablo 2 boss that got us all done again with Diablo 2 Resurrected.The fact that Duriel is the ‘Lord of Pain’ seems fitting considering he’s by far the most painful part of the game – I’d rather go toe-to-toe with Diablo itself on.

Annie Scott Riley, CMO of esports company Version 1:

“I’m still mad at Rennala, Queen of the Full Moon in Elden Ring. In her first stage, before you can damage her, you’ll have to attack these army-crawling, occasionally floating “scholars” who hurl books at you. This isn’t particularly difficult once you understand the warning signs of falling chandeliers – much chaotic? Then, in her second phase, you are transported to this moonlit, magical realm. It is distractingly majestic and its spells are insane; she summons shadows of other bosses to work with you.

“I’ll be honest, I couldn’t solo her at all, but with the help of a friendly stranger to divert her attention, I was finally able to take her out. Unfortunately, a millisecond later, I was struck by her final sorcery, which meant I ingested her runes and then died – in the realm of the second stage. Which will never, ever be accessible again. So I won, but I lost everything I came in with, plus what I would have earned. Nightmare fuel. Miyazaki is a great madman.”

Twitch streamer and YouTuber Hannahxxrose:

“My most feared video game boss is definitely the Ender Dragon in Minecraft. It’s super daunting to fight and there’s a big risk of losing your loot especially if you play the game fast. Despite playing the game for 8 years now, I only beat it once – and I needed help from some friends!”

Josh “Caru” GlodovezaVP of talent at fanjoy:

“For me, it’s Terraria’s Wall of Flesh. 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 until the end of the game map, until there is no more room to escape. I think it’s a great metaphor for life, about being cornered and having to make do with the situation you’re in. Though it’s the final boss before the game goes into Hardcore and opens up a whole host of even tougher challenges. That sounds like growing up to me. I can take on some of the biggest challenges right now, but that doesn’t mean they will stop coming, and I just have to adapt and take it day by day.”

Brian “Saintt” Baroska, Call of Duty League’s Head Coach Minnesota Smoke no:

“One of the toughest bosses I’ve ever encountered was the optional boss Sigrun in the most recent God of War game. That boss gave me so much trouble that I lowered the difficulty of the game from hard mode all the way to easy after dying over 100 times.

Twitch Streamer and Evil Geniuses team member ARUUU:

“I think my most feared boss of all time is Lady Yunalesca from Final Fantasy X. I often wonder if it’s because I was a kid when I played the game, or if it was really that hard. I remember crying to my brother to slap it for me because I was stuck with it for days. Overall, though, she’s pretty tough and felt almost impossible to beat. Even my brother got frustrated and annoyed by it.”

Mark Flood, director of North American operations at astralis:

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

(Continued:) “F Elden Ring.”

Michael Ashford, CEO of the Esports Awards:

Whitney’s Miltank [from Pokémon Gold and Silver] still gives me nightmares from 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 also this Digiday reporter’s choice.)

Washington Post games reporter Gene Park:

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

Paul Mascali, head of esports and gaming at PepsiCo:

“Personally, my most feared boss would be Jack of Blades from Fable. I always struggled with the second phase of that boss fight. It 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 definitely be Onyxia. These are the early 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 complicated to make a 40 person raid do all they needed to do, and it would reset for a week if you failed. Everyone wanted the drops, so only the fear of winning the roll if your class item fell. Just a stress fest.”

Twitch streamer (and 2K NextMakers mentor) Mitsou:

“The most feared in-game boss? The last boss of Half-Life, The Nihilanth. An imposing and challenging final boss, capable of teleporting you into dangerous side rooms, summoning powerful hovering enemies and having a very hard-to-reach weak spot – there’s no final boss fitting after traversing the already notoriously difficult world from Xen.

John Jung, VP of Operations and Studio at Evil Geniuses:

“Literally every boss in Witcher 3 scared me. I couldn’t play this game at night.”

Gil Hirsch, CEO and co-founder of StreamElements:

“After hitting all the combos in 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, repetition. Until you strike that final blow, excited and exhausted.”

Joshua Brill, head of marketing at Fnatic:

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

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