Lem Doolittle is one of the Strangers who acts as Shannon and Joseph's "guide" at the Hard Times Distillery. He appears as a glowing skeleton and works as a copywrighter at the Distillery.
The Entertainment
Doolittle is the is the writer of A Reckoning and A Bar-fly, two plays which were together adapted by Joseph for simultaneous performance as The Entertainment.
In real life, A Reckoning is based on playwright Eugene O'Neill's The Iceman Cometh, featuring a similar story and characters (this play, in turn, is thought of as inspired by Maxim Gorky's The Lower Depths, after which the tavern the Lower Depths is named.
A Bar-fly is based on Samuel Beckett's Act Without Words, a playwright whose play Waiting for Godot is quoted and referenced multiple times throughout Kentucky Route Zero.
Name
His name is a reference to Oliver "Doolittle" Lynn, the husband of Loretta Lynn (on whom Junebug is based), and possibly to Hilda "H.D." Doolittle, an American Imagist poet.