My top obscure picks would be Conquest: Frontier Wars and Civil War Generals 2: Grant, Lee, Sherman.
The former was released in 2001 and, like Age of Mythology, has excellent graphics for the time. At first glance it appears to be fairly standard, with three races, the Terrans, Mantis and Celearions (sound familiar?) battling it out using a variety of starship classes. However, C:FW is actually rather unique in that bases are constructed in orbit of a limited number of pre-placed planets, battles take place across what effective amount to multiple small maps connected up by a series of wormholes that serve as chokepoints, bases in different sectors must be kept "in supply" to headquarters buildings by building jump gates on the wormholes (which also lock down the wormhole and so must be destroyed before enemy ships can use the wormhole again) and finally all combat vessels carry a limited number of "supplies", which must be replenished by supply ships and/or certain types of platforms as they fire their weapons and use special abilities. The game also has a very nice Starship Troopers inspired soundtrack, good voice acting and a surprisingly decent storyline for its campaign (which is also worth noting as it manages to seemlessly mesh together ultimately getting to play as all three races over the span of one long campaign, as opposed to having a seperate campaign for each faction). I am admittedly rather biased because this is one of my favourite games from my childhood, but I still feel it's well worth checking out for any strategy fan.
The latter, meanwhile, was (I believe) released in 2000 and couldn't be more different to C:FW. It is a turn-based game that, as its name suggests, revolves around the American Civil War. Battles take place between Union and Confederate brigades across a hex-based map, very much like many of the old tabletop wargames out there but with the benefit of having the computer do all the number-crunching for the player. This is handy, as the game keeps track of a huge number of complex, realistic factors that go into determining how effective or ineffective any given unit will ultimately be in combat, from different weapon types all the way to the experience and skill of a unit's commander. The battles themselves are highly strategic, with flanking, rear attacks, morale failure, ammunition supplies, leader casulaties, headquarters units and cover amongst others all factoring in. This is, admittedly, a somewhat difficult game to get into, but once you master it, routing an entire enemy force clean from the field and being able declare victory half-a-day before the battle you're fighting historically ended is a turly satisfying experience. If you've got some time on your hands, this is a great game to explore.
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