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I use to have some of the games, pro skater 1 to 4, and rented some of the other ones, but in the last few months I decided to buy all of them again. Been playing them to death the last few weeks.
Pro skater 1-4.
Thug 1 and 2.
American Wasteland
Project 8
Proving Ground.
-3 is the most fun to skate in. I think its the combination of soundtrack, levels, esp the cruise ship and tokyo, and the revert, which lets you get higher combos. 3 also has an incredible soundtrack, best of the series. And best video of the series, Rodney Mullin's. Never get tired of it.
-4 might be the most underrated. It had some cool levels I had forgotten about, like college and san francisco.
-Project 8, best opening with kasabians club foot.
-2 and 3 have awesome soundtracks that will probably never be topped in a skateboarding game.