Tony Hawk's Pro Skater

Played this on the Dreamcast and I swear THPS1 changed the course of history. On its own it's a really fun game, with air-tight mechanics that finally brought the momentum and flexibility of skateboarding to video games, after many failed attempts. But also THPS1 more than any other video game liberated many young minds and taught them to skate and be defiant to authority. The fun of the game embraces the outlaw nature of skateboarding, involving everything from tresspassing to prohibited spots like malls to actually busting cop cars, all to a tastefully picked soundtrack(the theme song is "Police Truck" by Dead Kennedys for god sakes). This can all feel like very milquetoast messaging coming from a multi-million publisher who today is notorious for their exploitative business practices and tax dodging, but this message lives on. It isn't so much a video game as is a poignant view into an entire philosophy. It's the real shit.

It would be outdone by future and better games for its inclusion of tricks but THPS1 has all the basics you could possibly need. If you grew up on PC versions of the THPS games as I did, then you'll feel right at home with the Dreamcast port which avoids both the short draw-distance of the PSX version, and the low fidelity of the N64.