[2] At the age of 50, he achieved a measure of stardom for his role in the 1939 stage play The Man Who Came to Dinner and its 1942 film adaptation.

[10] He played himself[11] in Warner Bros.' fictionalized film biography of Cole Porter, Night and Day (1946), and the role of Professor Wutheridge in The Bishop's Wife (1947).

He played a former Shakespearean actor whose long fall onto hard times forced him to swallow his pride and take a role on daily network radio, becoming an unlikely star while sparring with his wife, Lily (Anne Seymour), and his wise-cracking maid, Agnes (Pert Kelton).

[6] He starred in a CBS TV adaptation of The Man Who Came to Dinner in 1954,[14] which he and some reviewers lambasted,[15][16] and appeared in other televised dramas in the series Best of Broadway.

[9][14][17] After completing his last film, Kismet (1955), he returned to radio for about a year, after which he was forced to retire due to ill health.

[23][24][25] Starting in 1939, Woolley was living with a gay companion, Cary Abbott, who had also graduated from Yale in 1911.

[26] According to Bennett Cerf in his 1944 book Try and Stop Me, Woolley was at a dinner party and suddenly belched.

"[18][27] In 1943, Alfred Hitchcock wrote a mystery story for Look titled "The Murder of Monty Woolley.