Get a closer look at some of Hollywood's perfect pairs.

Hollywood Power Couples

Get a closer look at some of Hollywood&#39;s perfect pairs.

"The Gentlemen" and "Slow Horses" return this fall, while the "Reacher" spin-off series "Neagley" makes its debut. See our guide of the biggest Fall TV and streaming releases.

2026 Fall TV and Streaming Watch Guide

&quot;The Gentlemen&quot; and &quot;Slow Horses&quot; return this fall, while the &quot;Reacher&quot; spin-off series &quot;Neagley&quot; makes its debut. See our guide of the biggest Fall TV and streaming releases.

See who dazzled on the red carpet and took home gold at the 78th Primetime Creative Emmy Awards.

Primetime Creative Arts Emmys: Photos We Love

Large and hearty Monty Woolley was born to privilege on August 17, 1888, the son of a hotel proprietor who owned the Marie Antoinette Hotel on Broadway. A part of Manhattan's elite social circle at a young age, he studied at both Yale (Master's degree) and Harvard and returned to Yale as an English instructor and coach of graduate dramatics. Among his students were Thornton Wilder and Stephen Vincent Benet.

Directly involved in the theater arts via his close association with intimate Yale friend and confidante Cole Porter, Monty directed several Broadway musicals and reviews, many in collaboration with Porter, including "Fifty Million Frenchmen" (1929) (an early success for Porter), "The New Yorkers" and "Jubilee" (1935). In 1936, at age 47, the witty, erudite gent had a career renaissance and gave up his Ivy League professorship once and for all in order to pursue the stage professionally. He took his first Broadway bow in the hit musical "On Your Toes" alongside Ray Bolger. Hollywood soon took notice and he began receiving supporting credit as assorted judges and doctors for such MGM fare as Live, Love and Learn (1937), Everybody Sing (1938), the Margaret Sullavan tearjerker Three Comrades (1938), Lord Jeff (1938), the Jeanette MacDonald/Nelson Eddy musical The Girl of the Golden West (1938) and Young Dr. Kildare (1938).

Typically playing cunning character leads and support roles, he was affectionately nicknamed "The Beard" by friend Cole Porter for his distinguished, impeccably-trimmed white whiskers. It was Monty who introduced Porter into the famed New York theater circle. Known for his sartorial elegance, ribald sense of humor and snob appeal, he and Porter were highly prominent carousers in the New York gay social underground.

Monty came into his own in 40s films, earning a best actor Oscar nomination for his role in the WWII drama The Pied Piper (1942), a supporting actor nod in another war classic, Since You Went Away (1944), and portrayed himself in the absurdly fictionalized (and sanitized) "biography" of Cole Porter entitled Night and Day (1946) starring a woefully miscast but admittedly flattering Cary Grant in the lead. A flashy delight in other movie roles, Monty received top billing in Irish Eyes Are Smiling (1944) with June Haver and Dick Haymes, playing a twinkle-eyed con man; appeared opposite Brit comedienne Grace Field in the English-humored Molly and Me (1945) and Holy Matrimony (1943); again with Cary Grant along with Loretta Young and David Niven as a professor in the perennial Christmas classic The Bishop's Wife (1947); plots against his own retirement in the mild comedy As Young as You Feel (1951) opposite another scene-stealing favorite, Thelma Ritter; and ended his film career with the role of Omar Khayyam in the glossy MGM operetta Kismet (1955).

Above all, however, Monty will be forever and indelibly cherished as the irascible (and definitive) radio personality Sheridan Whiteside in the stage and film versions of Kaufman and Hart's screwball classic The Man Who Came to Dinner (1941). Playing the razor-tongued, wheelchair-bound celebrity who wreaks havoc for everyone within knife-throwing distance, this would be the hallmark of his never-too-late-to-try career. He played another uppity and bombastic celebrity, this time a washed-up classical actor, in the more sentimental Life Begins at Eight-Thirty (1942), another role dripping with crusty sarcasm.

Monty appeared sporadically on radio and TV before and after his last filming in 1955. He died of kidney/heart problems in 1963 at the age of 74.

Monty Woolley in The Man Who Came to Dinner (1941)

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