Oloro Lich (EDH / Commander)

Oloro Lich makes a seemingly bad enchantment (Lich) work in spectacular and explosive ways. There are probably a few more flavorful Lich Commanders to select that meet the theme (Varina, Lich Queen perhaps?), but mechanically, Oloro's free lifegain each turn boosts the card drawing potential, so you don't have to invest much resources to go off once you commit.

The key is to not over commit too early. Don't play OG Lich or Nefarious Lich or Lich’s Mastery recklessly. Although there are several ways to protect them or avoid dying if they are removed, the best strategy is to be careful until you have a wincon or massive draw engine ready so your not sitting exposed very long.

The three Lichs are similar, but do work differently. They all contain the text "If you would gain life, draw that many cards instead." Neither is necessarily better than the other, but choosing which to tutor for is a in-game decision. The cards you play early will decide which of the Lich's are optimal. In all scenarios, you need to establish ways to give the enchantments shroud/hexproof, (Greater Auramancy) or not lose if something unexpected happens (Platinum Angel). Depending on which path you choose, the set-up isn't complicated. You are gaining a fair amount of life early, so blocking isnt necessarily important even if you are being pressured. Feel free to spend life in the interim to draw cards with Dark Confidant. If you go the OG Lich route, you're resetting to zero life anyways.

Once you establish board presence, you'll need to choose which Lich works best for your situation. Here is a run down of the synergies that differ between the two enchantments:

Plan A: OG Lich
1.) OG Lich reduces your life to zero. The wincons that work best here are Axis of Mortality, Repay in Kind, or Mirror Universe.
2) To defend with OG Lich, damage prevention effects are ideal.
a. Delaying Shield is great, because it prevents damage, and converts it to loss of life instead.
b.) Solitary Confinement is great, as you can stack Oloro's trigger with SC's upkeep to maintain.
c.) Phyrexian Unlife is your back-up plan.
3.) OG Lich combos great with Ad Naseum. You don't need to sacrifice permanents to Lich due to loss of life. Feel free to draw your entire deck at once, and go into negative life. You wont lose.
4.) OG Lich combos with Dark Confidant the same way.

Plan A.1 Nefarious Lich is a new addition, but operates much the same way as OG Lich as its damaged based. You will be a little more exposed with Nefarious though, as you likely won’t have a full graveyard as a fail safe. Hopefully you won’t have it exposed on the battlefield longer than a turn before you go off.

Plan B: Lich's Mastery
1.) Mastery doesn't reset your life to zero. You keep your life total, and can still gain life.
a.) You can stifle the lose game trigger if Lich's Mastery leaves the game. I like Tale's End as added value as a limited counterspell. Angel's Grace is similar.
b.) Platinum Angel is your back-up plan.
2.) Warning, Lich's Mastery doesn't work with Ad Naseum. If you lose life, you are forced to exile permanents/cards in hand.
3.) Lich's Mastery has Hexproof, so you don''t need as much set-up protection in the form of Greater Auramancy/Fountain Watch.
4.) Lich's Mastery works great with Sickening Dreams as a wincon, as you can discard half of your cards to Dreams, and the other half to pay for Mastery's exile trigger.
5.) Darien King of Kjeldor makes tokens, which can be sacrificed to Lich's Mastery in a pinch if you take damage. (Note, Darien does not work with OG Lich.)

Despite all of these these limitations, Lich & Lich's Mastery have the most important mechanic to draw when you gain life. There is a huge package of lifegain spells to choose rom, which all result in massive draw.
1.) Immediately draw your life total in cards with Tainted Sigil and/or Children of Korlis.
2.) Immediately draw your opponents life total in cards after exchanging life with Axis/Mirror Universe.
3.) BBBB and 3BBB are contribute a lot to black devotion for Gray Merchant, as does BBB from Phylactery Lich.
4.). Words of Worship multiplies card draw by a factor of five for one mana.

Other ways to win with 80+ cards in hand:
1.) Sickening Dreams: Discard half of your hand, and exile the other half to Lich's Mastery. Of course, ignore the second half if you have Solitary Confinement or Delaying Shield.
2.) Laboratory Maniac: Drawing your entire deck happens all the time.
3.) Psychosis Crawler: AoE damage based on card draw. If someone survives the initial draw, just attack them with an 80/80 Crawler.
4.) Queza Agur of Agonies can kill your last opponent, but will draw out your library in the process. Use this last.

If all else fails, hang in there and beat your opponent down with Phylactery Lich, any of the Angels, or Obzedat. Creature beats are perfectly acceptable.

Have fun living on the edge, but beware Cyclonic Rift and Tranquility!