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, studying there for a year, but quit to pursue theatre. He was later a recipient of the Alexander Hamilton Medal.