Born in Evansville, Indiana, he grew up in Michigan where his father was a Baptist minister. He went on to graduate from the University of Michigan. At the university, he formed a lasting friendship with Poet-in-Residence Robert Frost and earned a B.A. in English and an M.A. in psychology. Following a brief stint as a student of George Pierce Baker, the noted teacher of dramatic form and founder of the Yale School of Drama at Yale University, he made his debut on Broadway in 1928 with the play Hotbed. His next play A Ledge was produced the following season.
In 1930, Osborn found singular success on Broadway with a comedy titled The Vinegar Tree that starred Mary Boland. He contributed the comedy Oliver Oliver to the 1934 Broadway season, and in 1984 that play won critical acclaim at the Long Wharf Theater and the Philadelphia Drama Guild with Boyd Gaines in the title role. On the opening night in New Haven, the audience gave Oliver Oliver a standing ovation; and Osborn, who suffered macular degeneration, quipped, "I thought they were standing to get their coats."
Although often noted for his adaptations, Osborn's 1939 comedy, Morning's at Seven, became one of Osborn's most enduring original works. It was revived on Broadway in 1980, directed by Vivian Matalon, featuring a cast including Teresa Wright, Maureen O'Sullivan, Nancy Marchand and Elizabeth Wilson. It was hailed by Harold Clurman "as one of the best American comedies" Morning's at Seven has been presented several times on television, including a version directed by Matalon. In 2002, the Lincoln Center Theater mounted a well-received production with Elizabeth Franz, Frances Sternhagen, Piper Laurie and Estelle Parsons as the four sisters. The play received numerous nominations for awards, as did the acting ensemble, with Elizabeth Franz cited in particular

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