[3][4] A chance encounter with Zero Mostel[5] led him to start writing for radio personalities, including Henry Morgan, Hildegarde, Tallulah Bankhead, Phil Silvers, and Jackie Gleason.

[7] They purchased a 50-cent tourist book filled with Pennsylvania Dutch slang and returned to New York to write Plain and Fancy, which opened on Broadway on January 27, 1955 and ran for 461 performances.

[9][10][11] Richard Pletcher, founder and producer, dedicated The Round Barn Theatre stage to Stein in 1997 during its production of The Baker's Wife.

His greatest success[3] came from writing the book for the 1964 musical play Fiddler on the Roof, for which he won three major awards, including two Tonys.

Wonderful, The Body Beautiful, Juno, Take Me Along, Irene, Carmelina, The Baker's Wife, Rags, Enter Laughing and its musical adaptation, So Long, 174th Street.

[5][6] The Baker's Wife, written with Stephen Schwartz, was directed by Trevor Nunn in London in 1989 where it was nominated for an Olivier Award for Musical of the Year.

[16] The York Theatre, under Artistic Director James Morgan, went on to produce a critically acclaimed fully staged off-Broadway production of Enter Laughing: The Musical from September 3, 2008 through October 12, starring Jill Eikenberry and Michael Tucker.

Directed by Garry Hynes, with guest music direction by Eric Stern and musical staging by Warren Carlyle, Juno played for five performances, from March 27 – 30, 2008 at New York City Center and was the first presentation since the original Broadway staging in 1959 to use the original orchestration by Blitzstein, Hershy Kay and Robert Russell Bennett.

It originally opened on Broadway at the Winter Garden Theater on March 9, 1959, starring Shirley Booth and Melvyn Douglas and played a total of sixteen performances.