1. GTA: San Andreas (Xbox) - I've chosen the Xbox version for several reasons - the ability to export your pictures (with a chipped console), the vastly improved frame rates and performance, the custom soundtracks (I have a brilliant oldies station) and the far, far improved driving controls (though the helicopter controls are undeniably worse but this would cease to be an issue if you played on a 360 with a 360 pad). Basically, San Andreas has almost everything you could ever want to do. If you want to race, there's car races. If you want track and field button bashing, there's the triathlon. There's also fixed-wing and helicopter flying, train driving, crazy taxi-ing, truck driving, motorcycle stunts, dance dance revolution, side-scrolling shooters, a reasonable clone of Space Taxi (the bumblebee game), police/fire/ambulance games, three types of hand-to-hand combat, a jetpack, boats, a casino filled with games (including excellent blackjack), car pimping and tuning, radio-controlled toys, base jumping, homie road trips with a stolen bus, off road racing, skydiving...
Back when I was younger, I used to do a lot of this stuff in my previous #1 game, Stunt Island. However, Stunt Island was primarily a *shivers* machinima *shudders* tool, in which you could create scripted sequences for a variety of vehicles and props to go through, and then use a lovely editing suite to make a coherent (or otherwise) movie of the results. However, San Andreas lets me do all the things list above with proper structure, and in a proper living world that will respond to my actions. Granted, in the face of GTAIV it's hard not to miss some new features (taxis in particular) but GTA:SA remains my favourite game ever for the time being.
2. Transport Tycoon and OpenTTD (DOS/Windows/OS X) - Unquestionably the best world building/strategy/management game ever. Rollercoaster Tycoon and its progeny might have more mainstream appeal, but doesn't match the depth and flexibility and scope of Transport Tycoon. OpenTTD has removed all the limitations of the originals (due to the processing power and memory constraints of the hardware the game was originally programmed for) to give us a stupidly flexible, magnificent game. Primary industries produce (iron ore, coal, oil, wood), secondary industries refine (into goods, steel, etc) and the populations of cities demand it.
To get the materials from A to B to C(ity) you have planes, trains, trucks and ships, and the tools to build the vast infrastructure to support these - realistic signalled railways, road networks, airports and seaports. The local populace want to travel around too, so you can build passenger trains and buses to earn money that way too.
With its charming and familiar British setting (though you can mod it to anywhere in the world) and bright graphics, it's hard not to love Transport Tycoon. Yes, the AI opponents can't build efficient networks to save their lives and are little more than a distraction (most people don't bother playing 'against' them) but you'll be too absorbed in widening your main railway line to cope with the traffic from that new coal mine, or investing in the new-fangled Airbus model that has just been offered as an exclusive by the manufacturer.
Nothing has yet surpassed Transport Tycoon. Chris Sawyer's own Locomotion suffered from a lack of development, tiny maps and terrible pathfinding AI; freeware Simutrans has superior passenger modelling (in TT, people just board whatever bus or train or plane or ferry comes, regardless - in Simutrans, they have a specifc destination) but a hideously clunky interface; JoWood's 'Giant' series have been far too abstract and limited in their depction of transport networks.
3. Frontier: L33t 2 (PC, though lately I play it through UAE) - This needs no introduction, really. A vast galaxy, with endless adventures to be had. Gets repetitive as hell, but thankfully it's also compulsive as hell.
4. Star Control 2 (PC) - You'd have never imagined this would be the sequel to the original game, which gave us 20 varied space ships (with comedy aliens) to fight in a Space War-style arena battle, with a rudimentary strategy game shoehorned in.
Star Control 2, meanwhile, combines a bit of empire building, with customising your battlecruiser, and a bit of exploration and resource management... oh, and some adventure/RPG elements as you explore a vast section of galaxy in the aftermath of an invasion by the dreaded Ur-Quan. And this before the return of the outrageously entertaining Space War arcade combat bits. With some of the best music and dialogue ever written, and a huuuuge story spanning the even huuuugerer galaxy... this will delight you for weeks.
6. Fallout (PC) - Legendary roleplaying game. Released at a time when all RPGs were either tedious swords and beards nonsense (on PC) or 70-hour insta-battle grindfests (on consoles), Fallout won our hearts with its intriguing story, brilliantly written dialogue, original setting (what if the 1950s facade of the American Dream never ended?) and... TURN BASED COMBAT.
5. Skies of Arcadia (Dreamcast) - Delightful JRPG. The plot is ridden with cliché and saccharine, but it doesn't matter as you can't help but love the characters. The music is utterly magnificent. While the on-foot combat is pretty standard JRPG turn-based fare, the ship-to-ship combat is inspired and entertaining. As you build your crew and improve your ship, you get the genuine sense of being a great explorer, visiting exotic lands, meeting new civilizations and fighting off the evil empire. Like I said, ridden with cliché. But it's still one of my favourite stories of all time, as it's told so damn well.
6. Radar Mission (Gameboy) - Two games in one! An expanded version of Battleship, and an expanded version of Seawolf. Endlessly playable, some of the best graphics and music seen on the little handheld, I loves it I does.
7. Syndicate (PC) - The hours you could waste in this game doing whatever you wanted... come up with complex plans, plot exciting escapes, or just firing your guns to terrify civillians into running in front of speeding trains.
8. X-Com: UFO Defense (PC) - I love it. It gets a bit repetitive later on as you have to endure crashed UFO mission after crashed UFO mission while you wait for the World's Slowest Scientists to work out that the Plasma Gun Clip powers the Plasma Gun (duh!). The sequel (TFTD) was too hard, while the third-quel is arguably better with is pausable real-time combat, which greatly eases the tedium of endless samey missions by upping the pace considerably.
9 and 10 to come as and when I think of 'em.
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