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Painkiller Overdose
Painkiller Resurrection
Painkiller Redemption
Painkiller Recurring Evil
Painkiller Hell & Damnation
That is the chronological order. But you don't have to follow it, since there is no actual storyline that connects these games.
Now, when it comes to gameplay, leveldesign and overall quality, I'd recommend playing Black first, because it is easily the best game in the series.
Make sure you get the Widescreen Mod if you are using a 1080p monitor!
http://steamcommunity.com/sharedfiles/filedetails/?id=193714598
Overdose is okay-ish. There are some fairly well designed levels, but overall it is pretty messy and unpolished.
Resurrection, Redemption and Recurring Evil can all be skipped entirely. Trust me, they are absolutely dreadful.
Hell & Damnation is pretty decent, although just a remake of the original with less content. But it adds shiny Unreal 3 Engine visuals, improved splatter effects and a few new weapons.