Clouds, Lysistrata
by Aristophanes
Aristophanes, also known as "The Father of Comedy", was a comic playwright of ancient Athens. Eleven of his forty plays survive virtually complete. His powers of ridicule were feared and acknowledged by influential contemporaries.
The Clouds is a play in which the famous philosopher Socrates is presented as a petty thief, a fraud and a sophist. The Clouds was singled out by Plato as slander and a contributing factor that resulted in the trial and subsequent execution of his mentor Socrates.
Lysistrata is a comic account of a woman's mission to end the Peloponnesian War between Greek city states by denying all the men of the land any sex. Lysistrata persuades the women of the warring cities to withhold sex from their lovers in order to force them into negotiating a peace.
The 1 Penguin edition gives you both plays in an easy-to-understand translation with ample notes and commentary. One downside of this edition is that it uses end notes instead of footnotes, so you should expect some page-flipping. I like to use two bookmarks, one where I'm reading the main text, and one where I am in the notes, and forward them both as I progress through the book. It makes flipping between the two positions much easier.
For Lysistrata, there is also the 2 Hackett edition translated by Sarah Ruden, which is a highly accessible translation with lots of footnotes and commentaries on Athenian culture and Greek comedy.
You can find a great set of notes for Lysistrata and on The Clouds: Part I and Part II.