Wallace (Justin Long) co-hosts a popular podcast with his pal Teddy (Haley Joel Osment), focusing on cruel, mocking cringe humor as part of their mission to keep it "real and raunchy." After his trip to Winnipeg to interview the "Kill Bill Kid" - a teen whose unfortunate samurai-sword video has gone viral - comes up empty, Wallace decides to make the trip worth his while and find a good story north of the forty-ninth parallel. A handwritten flyer he finds in a bar bathroom leads him to a grizzled old swab (Michael Parks) full of tall tales to share from his life of adventure at sea - and this is where Wallace's voyage to the Great White North descends into straight-up madness.