Painful Quandary

Whenever an opponent casts a spell, that player loses 5 life unless they discard a card.

Nicol Bolas, the Arisen

+2: Draw two cards.
−3: Nicol Bolas, the Arisen deals 10 damage to target creature or planeswalker.
−4: Put target creature or planeswalker card from a graveyard onto the battlefield under your control.
−12: Exile all but the bottom card of target player's library.

Nicol Bolas, the Ravager

Flying
When Nicol Bolas, the Ravager enters, each opponent discards a card.
{4}{U}{B}{R}: Exile Nicol Bolas, the Ravager, then return him to the battlefield transformed under his owner's control. Activate only as a sorcery.

Nicol Bolas, the Ravager // Nicol Bolas, the Arisen

Bloodchief Ascension

At the beginning of each end step, if an opponent lost 2 or more life this turn, you may put a quest counter on Bloodchief Ascension. (Damage causes loss of life.)
Whenever a card is put into an opponent's graveyard from anywhere, if Bloodchief Ascension has three or more quest counters on it, you may have that player lose 2 life. If you do, you gain 2 life.

Exsanguinate

Each opponent loses X life. You gain life equal to the life lost this way.

Each player loses a third of their life, then discards a third of the cards in their hand, then sacrifices a third of the creatures they control, then sacrifices a third of the lands they control. Round up each time.

Gray Merchant of Asphodel

When Gray Merchant of Asphodel enters, each opponent loses X life, where X is your devotion to black. You gain life equal to the life lost this way. (Each {B} in the mana costs of permanents you control counts toward your devotion to black.)