Oscar Hammerstein
Oscar Hammerstein II CC 1916 was a writer, director, and producer of musicals. Hammerstein entered Columbia on a pre-law program and got his start writing and starring in the Varsity Show (his first was "On Your Way" in 1915). He was also a member of Pi Lambda Phi, along with future collaborator Richard Rodgers (together, they were popularly known as "Rodgers and Hammerstein").
He later entered the law school, but quit to pursue theatre. He was later a recipient of the Alexander Hamilton Medal.