New Line/Kobal/ShutterstockHow the 2000 first big-screen adaptation of Dungeons and Dragons originated was almost as fantastical as the RPG itself. Indeed, a decade earlier, a 19-year-old obsessive named Courtney Solomon had brazenly enquired about obtaining the rights to turn his favorite board game into a feature film. Remarkably, despite his tender age and complete lack of Hollywood experience, publisher TSR, Inc. eventually handed them over. Unfortunately, this dream scenario soon turned into a nightmare.It would take years for the project to start gathering pace, with Solomon spending 18 months seeking further funding alone. There was also a struggle to find a director — James Cameron, Francis Ford Coppola, and Stan Winston were just a few of the hotshots who chose not to act on their early interest — and a studio willing to take a punt on a genre which pre-Harry Potter/Lord of the Rings et al had become box office poison.Furthermore, Solomon and new business partner Allan Zeman then had to thwart plans to instead adapt D&D into a lower budget straight-to-video affair and TV series before finally accruing $30 million; Joel Silver’s involvement as executive producer prompting enough investors to part with their cash. Although still far shy of the $100 million target, this sum was deemed high enough for a green light. The shoot was subsequently transported from the States to the more cost-effective Czech Republic and, in another move which now seems unfathomable, Solomon himself took the director’s chair.The fanboy was certainly ambitious. Dungeons and Dragons was intended as the first part of a trilogy specifically designed to become fantasy’s answer to Star Wars and he promised to provide the wow factor at least 10 times in the opening half-hour. It could be argued he achieved the latter, although the gasps from the audience were more of second-hand embarrassment than wondrous amazement.Remarkably, despite the inherent shoddiness of the script and the blatant absence of filmmaking knowhow, Solomon managed to bag a relatively impressive cast. Looking for something a little more frivolous than the navel-gazing psychodrama of Oscar winner American Beauty, Thora Birch signed up to play Savina, the young Empress of fictional kingdom Izmir. Great British thespian Jeremy Irons — encouraged by his D&D-playing sons and, incredibly, the need to upkeep his recently acquired castle — agreed to portray dastardly Mages council leader Profion. And Marlon Wayans, who had a somewhat eclectic 2000 having also appeared in Scary Movie and Requiem for a Dream, took on the role of thieving sidekick Snails. Geekier viewers would no doubt also be impressed by bit parts for The Rocky Horror Picture Show legend Richard O’Brien and the fourth Doctor Who, Tom Baker.It seems fair to say, however, that Dungeons and Dragons won’t be at the top of anyone’s resume. Irons hams it up like a pantomime villain while spouting camp clangers like “Let their blood rain from the sky.” Savina is such an inconsequential blank page you soon forget Birch was even in the film. And poor Wayans, one of the few actors who had a familiarity with the game, is saddled with an offensive Black stereotype who’s unceremoniously thrown off a cliff.Justin Whalin as unconvincing hero Ridley. | Francis Delia/New Line/Kobal/ShutterstockIt doesn’t help that the bulk of the picture is steered by the slightly lesser name of Justin Whalin, best known as The New Adventures of Superman’s roving photojournalist Jimmy Olsen. While perfectly watchable providing comic relief as Lois and Clark’s sidekick, a leading man he is not. In fact, as Ridley, Whalin is upstaged in every scene, his attempts to play the dashing hero hindered by a distinct lack of chemistry with love interest apprentice Marina (Zoe McLellan) and a constant vacant expression which suggests he’s as baffled by the mythical quest as the rest of us.Good luck making sense of a story which centers around Savina and Profion’s battle to procure the Rod of Savrille, a MacGuffin of a device which allows them to seize control of the kingdom’s giant red fire-breathers. Throw in a dwarf played by permanently stooping 5’ 8” actor Lee Arenberg, a paladin elf sporting a Madonna-esque conebra, and a muscled heavy who can soak up enemies’ brains with monstrous ear tentacles, and it’s little wonder D&D left viewers truly perplexed.We’ve not even mentioned the porridge rug that quicksand-like nearly devours Snails whole (“It was probably the worst thing I've ever had to do in a movie,” Wayans later admitted), the medieval costumes which appear to have been raided from the nearest fancy dress bargain bucket, or the hopelessly inane dialogue which spells every development out in giant capital letters — in the most glaring example, Damodar taunts Smiles with, “Just like you thieves, always taking things that don't belong to you.” This is a film so unsubtle its opening shot consists of, yep you guessed it, a dragon in a dungeon.Bruce Payne as tentacled heavy Damodar. | Francis Delia/New Line/Kobal/ShutterstockOptimistically, Dungeons and Dragons ends with the gang, having dispatched with Profion and his minions, setting up a sequel with a glowing ruby that magically transports them to a completely different otherworld. Of course, grossing less than $34 million worldwide, and challenging Battlefield Earth for the most scathing reviews of Y2K, New Line Cinema executives chose to end the adventure there and then.To be fair, Solomon later acknowledged he was ill-equipped for the job, also pointing the blame toward meddling investors and those who insisted on using an earlier screenplay which wasn’t as respectful to D&D lore. And you have to admire the chutzpah of a novice plowing on with his cinematic vision regardless of the finances to do so.Furthermore, 2005’s Wrath of the Dragon God, which brought Payne’s Damodar back to life, and 2012’s The Book of Vile Darkness had just as much difficulty transferring the much-loved RPG for the screen. It took until 2023’s Honor Among Thieves to do Dungeons and Dragons justice, and even that failed to bring in big numbers. Still, its original outing sadly remains the franchise’s nadir. “Be prepared for a lesson in pain,” O’Brien’s Xilus tells Damodar during a laughable war of words, a warning also applicable to any dice throwers who were expecting a faithful fun ride.