Tony Hawk's Pro Skater (Multiplatform, 1999)

I will admit that the first time I played Tony Hawk's Pro Skater (1999) was not at the time of its release.  My cousin let me have his old Playstation sometime in the late 2000's, and this was one of the first games I bought for it.  To my amazement, the game was not as dated as I might have expected.  Sure, it reeks of the late 90's, but it more captures the spirit of that time than keeps itself stuck there.  In concept, it should have been a bad game.  It was made to cash in on the popularity and success of skateboarding legend (then a new star) Tony Hawk.  By design, it is one of the best games about the sport.
The game needs not much of a plot, other than you are a skateboarder of your choosing (there are ten to choose from but most people will stick with Hawk) and you are trying to skate your way to fame.  There are a number of city locations where you have several missions to complete to earn tapes (remember VHS?).  Once you have enough tapes, you can move on to the next location.  There are also three competitions where you have to perform to your best ability to get a medal.  Only the most acrobatic will achieve extreme sports glory.
The two big factors that make this game a gem are the control and the level design.  Maneuvering a skateboarder and pulling off tricks could have been an exercise in frustration, but the control setup feels natural and tight.  You move forward automatically, turn with left and right, and stop by holding down.  Press and hold one action button and you will lean to go faster, and release it to jump.  For tricks, hold any one of the eight directions and one of the four action buttons.  You can build a chain of tricks for a maximum score, but be careful, because if you fall you lose all of those points.
Level design complements the control flawlessly.  Each level offers infinite possibilities for trick combinations, as well as secret areas.  To earn tapes, you will have to go around each stage and complete certain objectives within a time limit.  There are some that are similar in each stage, for instance, collecting the five letters of the word SKATE, or getting a certain amount of points.  Others are stage specific, like in San Francisco you will have to grind five police cars.  Beside earning tapes, it is simply a joy exploring each level and finding all the best ways to pull off tricks.
I'm fairly sure that many of the maneuvers you pull in this game are physically impossible.  I suspect that no skater (not even Mr. Hawk) has successfully ramped up a quarter-pipe to grind on a rail at least a story higher, and then ollied back to the ground with no injury.  But I don't play this game (or any game) for stark realism.  This game is about the joy of skateboarding, and the fun and mastery behind it.  There is a certain rush I get from zooming around a level pulling off impossible tricks, boldly defying gravity and physics.
The Tony Hawk series was immensely popular for a while, receiving three sequels and a number of spin-offs, each one successively losing that tremendous feeling of flight.  It had a direct influence on the Skate series of games and other extreme sports games, but none of them feel as right as Tony Hawk's Pro Skater.  Skateboarding is still around, but it is not nearly what is was back in the 90's.  Pro Skater perfectly captures its day and age without feeling archaic.  A well designed game is timeless, even if it does reflect a certain time period.