* AlternativeCharacterInterpretation: Was the Sheriff all that bad? Was Robin Hood such a hero? Robin can seem like a real GoodIsNotNice hero several times through the movie, while the Sheriff is something of a PunchClockVillain just doing his job.
** The Sheriff tried to force Marion into marriage, and later tried to rape her. Yes, he is evil. If anyone, Prince John is a more sympathetic villain; just a dopey man trying to relax and not lose his position of power.
* AngstWhatAngst: Robin has a brief moment of distress at finding his family dead upon his return, then shrugs it off and begins his new life of adventure.
* BigLippedAlligatorMoment: The ''HomeAlone'' parody bit (with the kid running around and shouting) doesn't withstand the test of time and just comes off as odd now.
** For some though, this left-field oddness makes the scene even funnier. If nothing else, the boy who plays the Young Lad is fantastic.
* [[CrowningMusicOfAwesome Crowning Music of]]... [[CrowningMomentOfFunny Funny?]]: The musical switchups during Robin and Little John's staff fight. It gets faster and sillier the shorter their staffs get, then finally turns into a chirpy, cartoonish ditty when they're reduced to smacking each other's knuckles with sticks.
** Rottingham's "theme": Da daaaaaaaaaaaaah, dadadadadadaaaaaaaaaaaaaaah, dadadadadada-da-da, dada-da-DAAAAAAAAAAAAAAAAAAAAAAAAAH!
** The "Men In Tights" song.
* HilariousInHindsight: This was [[DaveChappelle Dave Chappelle's]] first film. Who would have guessed he would later make a successful and over-referenced gag out of a guy named Lil Jon?
** Will Scarlett O'Hara is played by Matthew Porreta, who ''played'' Robin Hood later on in a TV series. [[note]]Which was riding on the popularity of Kevin Sorbo's ''Hercules'' series at the time, rather than any Robin Hood property. There was also a ''Sinbad'' series then.[[/note]] They replaced him in the role long before it was discontinued.
** A minor one, but the Italian assassin who Don Giovanni dispatches to kill Robin? His name is "Dirty [[VideoGame/AssassinsCreedII Ezio.]]"
* HoYay: Prince John and the Sheriff of Rottingham, in ''spades''.
* OneSceneWonder: Creator/PatrickStewart as [[RichardTheLionHeart Richard the Lionhearted]].
-->'''Rabbi Tuckman:''' ''[[Film/HistoryOfTheWorldPartI It's good to be the king.]]''
** Rabbi Tuckman, who is one of the most iconic characters of the movie but appears in only two scenes
** The Young Lad. Though his scene is a cheap HomeAlone gag, the young actor's over-the-top performance makes it one of the funniest scenes in the movie.
* SpecialEffectsFailure: Blinkin runs into what is obviously a fake tree at one point.
* UglyCute: Latrine.