Hello!
The difference between the two would be that a challenging game puts you through obstacles that require you some skills to beat it (not exactly the exact opposite of facerolling a game but close) and you CAN beat it. And for "the hardest" I mean games that are almost impossible to beat/take very much skill/time(or more likely devotion) to beat. Oh,and these are pretty much unrelated to difficulty levels,as most games are challenging and hard on high difficulty levels, at this post try to concentrate on games that are challenging or hard by default.
I'd give examples too:
challenging : Far Cry, Driver: Parallel Lines(shaking off the cops)
hardest : El Matador, Driv3r (some driving missions)
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