Bob R.’s review published on Letterboxd :
Chris Elliott is a funny, funny dude. Cabin Boy, however, is at best a mixed bag. Elliott plays a recent boarding school graduate, who's sense of entitlement rubs absolutely EVERYONE the wrong way - including the viewer most of the time. It's a fun cast for sure including Ann Magnusson, Brion James, Andy Richter and an incredibly rare acting appearance from David Letterman. The problem is just one of inconsistency. The adult-actor playing an adolescent/childlike character didn't work this time, and what could have been another "Pee Wee's Big Adventure" ends up looking more like "Clifford."