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I've had the option to fight him twice now before the second encounter with Vergil. The battles feel so out of context with what's happening storywise. There is no apparent reward either when you win?

I'm playing the recently released HD-version.

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up vote 2 down vote accepted

Orbs, Style Points and Experience. There isn't a really good reason to bother with the optional fights even though the first of the 3 is mandatory.

The Jester fights were additions to the Special Edition which have apparently also been migrated to the HD release. As they were apparently not part of the original game, that may be why they feel out of place.

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Thanks, I wonder why the developers went out of their way to add those fights? – MdaG Apr 20 '12 at 22:19
Apparently, "In the story at the end of Mission 13 Jester comes and says 'I had to make you fight each other in order to weaken you, but at the same time, I had to guide you here and make sure you were kept alive'", but I don't see that as a reward. It's definitely strange that they added it and I haven't read anywhere as to the reason though. – skovacs1 Apr 21 '12 at 0:58

The reason for fighting Jester in the HD version is for an achievement

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