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I have many, many fond memories of Oblivion. But I truly feel Skyrim is a better entry point for getting lost in the game. It's just better put together. Now, it does look slightly dated now but if you are on PC with a fairly strong rig, that is easily fixed with mods. The Nexus mod sites have a ton of great overhauls for the aesthetics. Skyeim Flora Overhaul and one of the many HD texture packs plus Imaginator are all things I highly, highly recommend. Same goes for Oblivion but even the best mods can only make such an old game look so good.