* AwesomeDearBoy: Creator/AlanRickman turned down the role of the Sheriff twice before he was told he could more or less have carte blanche with his interpretation of the character.
* BreakawayPopHit: Music/BryanAdams' "Everything I Do (I Do It For You)".
* DawsonCasting: Sixty-one-year-old Creator/SeanConnery as thirty-seven-year-old UsefulNotes/RichardTheLionheart.
** Could double as ArtisticLicenseHistory, as the producers wanted Connery in the film in some way, and after he turned down being Robin Hood's father, Richard was the most likely role after that (and he is a very kingly actor).
* DuelingMovies: With another film called ''Film/{{Robin Hood|1991}}'' that was also released in 1991. That film starred Patrick Bergin as Robin and Creator/UmaThurman as Marian. In the U.S., it got shunted off to TV because of this film, but it was released theatrically in other countries.
** Can also be considered this with the comedy ''Film/RobinHoodMenInTights'' and, of all things, the animated Disney version of ''Disney/RobinHood'', which made a small TakeThat to this film in the commercial for its [[Creator/WaltDisneyHomeVideo 1991]] ''Walt Disney Classics'' video reissue.
* FakeBrit: Creator/KevinCostner, Creator/MaryElisabethMastrantonio, Creator/ChristianSlater, Creator/MichaelWincott and Creator/MichaelMcShane.
* FakeNationality: The African-American Creator/MorganFreeman plays a Muslim.
* FatalMethodActing: Averted. Creator/BrianBlessed was almost killed filming his death scene.
* MoneyDearBoy: For his unbilled walk-on cameo at the end, Creator/SeanConnery recevied $1 million. Which he donated to charity.
* [[NotNamedInOpeningCredits Not Named in Closing Credits]]: The cast list does not include any mention of Creator/SeanConnery as King Richard.
* ReCut: An extended version was released on DVD that gives some backstory to The Sheriff and Mortiana.
* ThrowItIn: Creator/ChristianSlater ad-libbed Will Scarlett's line of "Fuck me, he cleared it!", after Robin and Azeem are catapulted over the castle wall. Creator/KevinReynolds kept it in the film because it was funny, despite the historical inaccuracy.
** Creator/AlanRickman ad-libbed the line about cancelling Christmas.
* TropeNamers: CutHisHeartOutWithASpoon
* WhatCouldHaveBeen: This early draft is a lot more fantastical than the final version http://www.imsdb.com/scripts/Robin-Hood-Prince-of-Thieves.html.
** Creator/RobinWright was set to play Marian, but she had to drop out due to her pregnancy, and Mary Elizabeth Mastrantonio signed on to replace her.
** Creator/MelGibson was originally offered the role of Robin Hood. He turned it down, not wanting to do another period piece after starring in Creator/FrancoZeffirelli's ''Theatre/{{Hamlet}}''.
** Creator/SeanConnery was first offered the cameo of Lord Locksley, but passed as he felt he had been playing a lot of fathers in recent years.
** Creator/JohnnyDepp turned down the role of Will Scarlett.
** Creator/JonFinch, Creator/MichaelGambon, Creator/RichardEGrant, Creator/JohnHurt, Creator/IanMcKellen, Creator/SamNeill, Creator/OliverReed and Creator/PatrickStewart were considered for the Sheriff of Nottingham.
** Creator/ElizabethHurley, Creator/PatsyKensit, Creator/NicoleKidman, Creator/MathildaMay, Creator/AmandaPays, Creator/JoelyRichardson and Creator/AllySheedy were considered to play Marian. Creator/SophieMarceau auditioned for the role.
** Creator/CaryElwes was offered the role of Robin Hood and turned it down because he thought the plot was too contrived. He did however portray the character in ''Film/RobinHoodMenInTights''.