From a particularly infuriating tutorial level to the Souls games, these are our picks for 25 of the most challenging video games of all time. 1 of 25. 'Bloodborne' ... 2 of 25. 'Contra' ... 3 of 25. 'Cuphead' ... 4 of 25. 'Dark Souls' ... 5 of 25. 'Demon's Souls' ... 6 of 25. 'Dragon's Lair' ... 7 of 25. 'Driver' tutorial. ... 8 of 25. 'Dwarf Fortress' More items... Aug 16, 2024