In no particular order:

FernGully Tennis Tour – 1992 – NES

FernGully Tennis Tour lets you participate in what the instruction booklet calls "the rain forest's first and zaniest tennis tournament!" What FGTT lacks in realism, it makes up in pure fun factor. The game's labyrinthine plot can be hard to follow if you aren't familiar with the film, but you most casual players will skip it anyway. If you're lucky enough to have the rare NES 4-player adapter, here's one of the few games to support it. Watch out for anyone who picks Batty Koda though – he's flat out over powered.

The Crying Game Game – 1992 – Game Boy

Since there wasn't really a market for mature video games in 1992, the The Crying Game Game went overlooked by most. Fourteen years later the game has gained a cult following, and it's not hard to see why. This platformer features levels that put a new spin on old themes, like the upside-down planet of Xarxaxaphon and all it's lightning dragons. The final boss battle with Grimbold Daggerbreaker provides one last twist which we dare not ruin here.

The Fun fact – upon it's release in 1992, Gamepro gave The Crying Game Game it's first perfect 5.

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Risky Business – 1983 – Atari 2600

The film Risky Business was a biting satire of youth and the American dream. The game Risky Business continues that idea, except the American dream is represented by green blocks you collect while avoiding Guido the Killer Pimp (represented here by a blue smiley face). The primitive beeps and boops trying desperately to emulate Bob Seger are not to be missed. The highlight of the game? The hilariously crude drawing of a man in his boxers sliding across the floor with no animation you see every time you clear a maze.

Risky Business may not stack up against modern movie-game classics like Enter the Matrix and Stealth: The Game but it stands out as one of the first great movie tie-in games.

Cool Runnings Bobsled Jamboree '94 – 1993 – Genesis

Just like the real Jamaican Bobsled team that inspired the movie that the game is based on, Cool Runnings Bobsled Jamboree '94 challenged America's preconceived notions. Nobody believed a bobsledding game could be fun. Bobsled Jamboree proved them wrong with intense bobsledding sequences and an innovative control scheme. The game's later time trial levels are maddeningly difficult. It doesn't help that every crash means you once again have to hear the game's lone voice sample – a horribly digitized "feel the rhythm, feel the ride."

The '94 in the title seems to imply that they were planning future versions of the title, which unfortunately never materialized.

The Whole Nine and a Half Yards – 2003 – PlayStation 2 – 2003

The Whole Nine and a Half Yards isn't on this list because of it's game play, but rather because of it's storytelling. Here's a game that isn't content to just retell the events of a movie – this is a game that adds to it. As you may have inferred, the story takes place between the events of The Whole Nine Yards and The Whole Ten Yards. The game is a pretty even split of action sequences with Bruce Willis' character Jimmy the Tulip and puzzle solving with Matthew Perry's Oz. The Whole Nine and a Half Yards also features the vocal talents of an excellent Bruce Willis sound-alike and Matthew Perry. The game can get monotonous by the fourth boat chase, but still gets high marks for providing a completely new script funny enough that it could have easily been a third Yards movie. Franchise creator Mitchell Kapner has even declared this game canonical.

Later games that were influenced by The Whole Nine and a Half Yards and the way it expands on it's source matierial include Enter the Matrix for the PS2 and Police Academy: Lunar Mission for the Gameboy Advance.