Born on August 23, 1868 to Emma J. Dexter and Hardin Wallace Masters in Garnett, Kansas, his father had briefly moved to set up a law practice. The family soon moved back to his paternal grandparents' farm near Petersburg in Menard County, Illinois. In 1880 they moved to Lewistown, Illinois, where he attended high school and had his first publication in the Chicago Daily News. The culture around Lewistown, in addition to the town's cemetery at Oak Hill, and the nearby Spoon River were the inspirations for many of his works, most notably Spoon River Anthology, his most famous and acclaimed work. Spoon River was Masters's revenge on small-town hypocrisy and narrow-mindedness. It gained a huge popularity, but shattered his position as a respectable member of establishment.
Masters attended The Knox Academy from 1889-1890, a defunct preparatory program run by Knox College, but was forced to leave due to his family's inability to finance his education.
After working in his father's law office, he was admitted to the Illinois bar and moved to Chicago, where he established a law partnership with Kickham Scanlan in 1893. He married twice. In 1898, he married Helen M. Jenkins, the daughter of a lawyer in Chicago, and had three children. During his law partnership with Clarence Darrow, from 1903 to 1908, Masters defended the poor. In 1911, he started his own law firm, despite the three years of unrest (1908-1911) due to extramarital affairs and an argument with Darrow.
Two of his children followed him with literary careers. His daughter Marcia pursued poetry, while his son, Hilary Masters became a novelist. Hilary and his half-brother Hardin wrote a memoir of their father.
Masters died at a nursing home on March 5, 1950, in Melrose Park, Pennsylvania.He is buried in Oakland cemetery in Petersburg, Illinois. His epitaph includes his poem, "To-morrow is My Birthday" from Toward the Gulf (1918):
Good friends, let’s to the fields…
After a little walk and by your pardon,
I think I’ll sleep, there is no sweeter thing.
Nor fate more blessed than to sleep.
I am a dream out of a blessed sleep-
Let’s walk, and hear the lark.
Masters first published his early poems and essays under the pseudonym Dexter Wallace (after his mother's maiden name and his father's middle name) until the year 1903, when he joined the law firm of Clarence Darrow.
Masters began developing as a notable American poet in 1914 , when he began a series of poems (this time under the pseudonym Webster Ford) about his childhood experiences in Western Illinois, which appeared in Reedy's Mirror, a St. Louis publication. In 1915 the series was bound into a volume and re-titled Spoon River Anthology. Years later, he wrote a memorable and invaluable account of the book’s background and genesis, his working methods and influences, as well as its reception by the critics, favorable and hostile, in an autobiographical article notable for its human warmth and general interest.
Though he never matched the success of his Spoon River Anthology, Masters was a prolific writer of diverse works. He published several other volumes of poems including Book of Verses in 1898, Songs and Sonnets in 1910, The Great Valley in 1916, Song and Satires in 1916, The Open Sea in 1921, The New Spoon River in 1924, Lee in 1926, Jack Kelso in 1928, Lichee Nuts in 1930, Gettysburg, Manila, Acoma in 1930, Godbey, sequel to Jack Kelso in 1931, The Serpent in the Wilderness in 1933, Richmond in 1934, Invisible Landscapes in 1935, The Golden Fleece of California in 1936, Poems of People in 1936, The New World in 1937, More People in 1939, Illinois Poems in 1941, and Along the Illinois in 1942.
Masters was awarded the Mark Twain Silver Medal in 1936, the Poetry Society of America medal in 1941, the Academy of American Poets Fellowship in 1942, and the Shelly Memorial Award in 1944.
I have known the silence of the stars and of the sea,
And the silence of the city when it pauses,
And the silence of a man and a maid,
And the silence of the sick
When their eyes roam about the room.
And I ask: For the depths,
Of what use is language?
A beast of the field moans a few times
When death takes its young.
And we are voiceless in the presence of realities --
We cannot speak.
A curious boy asks an old soldier
Sitting in front of the grocery store,
"How did you lose your leg?"
And the old soldier is struck with silence,
Or his mind flies away
Because he cannot concentrate it on Gettysburg.
It comes back jocosely
And he says, "A bear bit it off."
And the boy wonders, while the old soldier
Dumbly, feebly lives over
The flashes of guns, the thunder of cannon,
The shrieks of the slain,
And himself lying on the ground,
And the hospital surgeons, the knives,
And the long days in bed.
But if he could describe it all
He would be an artist.
But if he were an artist there would be deeper wounds
Which he could not describe.
There is the silence of a great hatred,
And the silence of a great love,
And the silence of an embittered friendship.
There is the silence of a spiritual crisis,
Through which your soul, exquisitely tortured,
Comes with visions not to be uttered
Into a realm of higher life.
There is the silence of defeat.
There is the silence of those unjustly punished;
And the silence of the dying whose hand
Suddenly grips yours.
There is the silence between father and son,
When the father cannot explain his life,
Even though he be misunderstood for it.
There is the silence that comes between husband and wife.
There is the silence of those who have failed;
And the vast silence that covers
Broken nations and vanquished leaders.
There is the silence of Lincoln,
Thinking of the poverty of his youth.
And the silence of Napoleon
And the silence of Jeanne d'Arc
Saying amid the flames, "Blessed Jesus" --
Revealing in two words all sorrows, all hope.
And there is the silence of age,
Too full of wisdom for the tongue to utter it
In words intelligible to those who have not lived
The great range of life.
And there is the silence of the dead.
If we who are in life cannot speak
Of profound experiences,
Why do you marvel that the dead
Do not tell you of death?
Their silence shall be interpreted
As we approach them.