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I'm still blown away by GTA IV's openness
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The best and I mean BEST play through to do is what's called The Possible Trinity, it involves playing GTA IV and it's 2 expansions, The Ballad of Gay Tony and The Lost and the Dammed missions in a specific chronological order.
It really makes the excellent writing standout and is like being part of an interactive drama series that's like The Sopranos and The Wire.
https://gtaforums.com/topic/430301-the-possible-trinity/
It's my favourite gaming memory ever.
I remember playing these DLC's but I don't remember the specific plots anymore.
But I do remember that I felt very "in-character" with each one of them due to being different neighborhoods, missions and vehicles they used.
Yeah Rockstar put so much into the world building for Liberty City. The writing was really good.
And then beat GTA V for every cent it could with paling content.