* ActorAllusion:
** Randolph attempts to discredit Sheldon by tricking him into performing at a [[Film/AmericanHistoryX neo-Nazi rally]].
** Another [[Film/AmericanHistoryX AHX]] ShoutOut -- Sheldon pointing a gun at Burke and saying "You just fucked with the wrong rhino". Norton's character exclaims "You just fucked with the wrong bull" [[spoiler:before murdering the man who tried to steal his car.]]
** Elements of Rainbow Randolph, an actor who does a lot of kid-friendly fare, but is actually very foul mouthed, is more than a bit like Creator/RobinWilliams in real life. Really the main difference between the two is that Randolph is a scumbag, and Williams definitely was not.
* BoxOfficeBomb: It grossed $8,382,938 during its theatrical release, barely a sixth of its $50 million budget. Danny De Vito starts his DVD commentary with "I guess the mourning period is over."
* CreatorKiller:
** ''Death To Smoochy'' killed writer Adam Resnick's cinematic career completely after several failed screenplays previously. Resnick has only worked in TV since.
** Danny De Vito only directed one more film after this, the BenStiller comedy "Duplex", which also flopped. Fortunately he'd rebound on ItsAlwaysSunnyInPhiladelphia.
* OldShame: Jon Stewart brings his work in the film up a lot as SelfDeprecation, often to contrast his resume with the work of a much more successful actor.
* PlayingAgainstType: Harvey Fierstein, known for playing CampGay characters, plays a gangster.
** Creator/RobinWilliams, best known for playing lovable ManChild characters, plays a straight up asshole as Rainbow Randolph. Williams joked in an interview that his friends called this movie, ''{{Film/Insomnia}}'', and ''Film/OneHourPhoto'' his "trifecta of evil."
* WhatCouldHaveBeen: Among the auditionees for the part of Spinner, the brain-damaged boxer, was Music/HenryRollins. Rollins tells the [[http://www.youtube.com/watch?v=KSm0LZhVSnE story of his audition here]].