Douglass is a masculine given name of Scottish origin, derived from the Gaelic words "dubh" meaning "dark" and "glas" meaning "stream" or "water inlet." It is believed to have originated in the 12th century as a descriptive name for someone who lived near a dark stream or inlet.

The name Douglass first appeared in historical records in the 12th century, associated with the Douglas family, a prominent Scottish clan. One of the earliest recorded bearers of the name was William de Douglasdale, who lived in the late 12th century and whose name referred to the lands of Douglasdale in Lanarkshire, Scotland.

In the 14th century, the Douglas family rose to prominence through their military service and political influence. Sir James Douglas, also known as the "Black Douglas" (c. 1286 – 1330), was a renowned Scottish soldier and one of the leading commanders in the Wars of Scottish Independence against England. His bravery and loyalty to King Robert the Bruce earned him a place in Scottish folklore and history.

The name Douglass has been borne by several notable figures throughout history. One of the most famous was Frederick Douglass (1818 – 1895), an American social reformer, abolitionist, orator, writer, and statesman. Born into slavery, he escaped and became a prominent leader in the abolitionist movement, working tirelessly for the abolition of slavery and advocating for the rights of enslaved people.

Another notable bearer of the name was William O. Douglass (1874 – 1957), an American architect and designer who pioneered the Prairie School of Architecture in Chicago. His most famous works include the Douglass House and the Douglass Tomb, both located in Illinois.

In literature, one of the earliest references to the name Douglass can be found in the epic poem "Sir Gawain and the Green Knight," dated to the late 14th century. The poem mentions a character named Sir Douglass, a knight of Arthur's Round Table, who plays a minor role in the story.

Other notable individuals named Douglass include Andrew Ellicott Douglass (1867 – 1962), an American astronomer and archaeologist known for his pioneering work in dendrochronology, and Douglass C. North (1920 – 2015), an American economist and co-recipient of the 1993 Nobel Memorial Prize in Economic Sciences.