Vint Lawrence, a cartoonist and former contributing editor at the New Republic, died on April 9 at 76. Lawrence lived a fascinating, multifaceted life: In the early 1960s, he served in Laos as a CIA paramilitary officer, where he helped organize a secret guerrilla war against communist forces. After returning to the United States in 1964, he abandoned a blooming career in government to become an artist. He caricatured everyone from Donald Trump to Leo Tolstoy, depicting them with a potent mix of both humor and honesty.

To mark his extraordinary life, the New Republic has compiled a number of his memorable illustrations for the magazine.

Donald Trump, 1988

Diana Ross, 1991

Leo Tolstoy, 1992

Leo Tolstoy, 1982

George Washington, 1989

Ronald Reagan, 1984

Barbara Bush, 1992

David Foster Wallace, 1997

Machiavelli’s prince, 1983

Bill Clinton, 1999

George H.W. Bush, 1988