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Critical Role's Liam O'Brien reveals the key to most great heist movies: The plan fails
Along with fellow Critical Role star Marisha Ray, O'Brien penned the Legend of Vox Machina season 4 episode De Rolo's Eleven

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You may recall Popverse reporting on one of the more difficult things that Critical Role star Marisha Ray has ever written in her tenure as high fantasy expert - The Legend of Vox Machina season 4, episode 5. The episode, entitled De Rolo's Eleven, works like a classic heist film, and recently, Ray's co-writer (and OG Roler) Liam O'Brien spoke to something that may shed light on what made the process so difficult.
That is, for a heist to work in fiction, the thieves' original plan has to fail.
That's what we gathered from an interview The Mighty Nein star did with The AV Club ahead of the show's season 1 debut on Prime Video. Speaking specifically about episode 5, O'Brien told the outlet that he and Ray "wanted it to have all the qualities that make heists exciting," which meant, "treating it like a Rube Goldberg machine because every part of that machine affected another part of it."
The thing is, though, said Rube Goldberg machine couldn't work too well, else it spoil the audience's fun.
"Oftentimes with great heist movies," O'Brien continued, "They have a great plan, but then the plan breaks, and you have to see them improvise in the moment and still get to the end."
Without getting into too many spoilers here, that's a pretty fair assessment of what happens in De Rolo's Eleven, as well as the Ocean's films from which its name is derived. One thing that did go off perfectly, though, was the emotional arc of the episode. On IMDb, the episode currently holds an 8.7/10 rating.
Which sounds, to me, like a plan that's come together pretty well.
With two animated series on Prime Video, Campaign 4 in full swing, and so much more Exandrian lore to come, Critical Role is showing no signs of slowing down. That's why the adventuring party at Popverse are here to bring you everything we can from those nerdy-ass voice actors & Bo., including:
- Critical Role release schedule
- Critical Role's Campaign 4 characters ranked
- How to watch Critical Role in order
- Ways for you to relive the Critical Role panel from ECCC '26
- Taliesin Jaffe on playing Mollymauk Tealeaf for Campaign 2 vs. playing him for Prime Video
- Matt Mercer's homebrew warrior class (created originally for Vin Diesel)
...and much, much more. Roll initiative, player. Magic awaits.
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