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Robert Morse, the impish actor and singer who found early fame and success as the Tony Award-winning star of Broadway’s How to Succeed in Business Without Really Trying and enjoyed a late-career second act as an eccentric elder statesman of advertising in AMC’s Mad Men, died yesterday. He was 90.

His death was confirmed by son Charlie to Los Angeles’ ABC affiliate Wednesday night, and was announced on Twitter this morning by Larry Karaszewski, a writer, producer and VP on the board of governors for the Academy of Motion Picture Arts and Sciences.

“My good pal Bobby Morse has passed away at age 90,” Karaszewski wrote. “A huge talent and a beautiful spirit. Sending love to his son Charlie & daughter Allyn. Had so much fun hanging with Bobby over the years – filming People v OJ & hosting so many screenings (How To Succeed, Loved One, That’s Life).”

Additional information on Morse’s death were not immediately available.

A two-time Tony Award winner (for 1961’s How To Succeed and, later, the 1989 Truman Capote one-man stage bio Tru, Morse was Emmy-nominated seven times, including a win for the 1992 American Playhouse presentation of Tru. Five of his Emmy nominations were for Mad Men.

Instantly recognizable for his offbeat, gap-toothed appearance and mischievous demeanor, Morse was born May 18, 1931 in Newton, Massachusetts, and served in the U.S. Navy during the Korean War before launching his show business career in 1954 as an original cast member of the TV daytime serial The Secret Storm.

The following year, Morse made a strong impression on Broadway as young Barnaby Tucker in The Matchmaker, the play that would form the basis of the musicalized version Hello, Dolly! In the Broadway staging, Morse appeared opposite star Ruth Gordon, and he reprised the role for the 1958 film adaptation with Shirley Booth.

Next on Broadway and in quick succession were his Tony-nominated turns in two musicals: 1958’s Say, Darling, and, a year later, Take Me Along.

His signature role would arrive in 1961, when he played the ambitious window-washer J. Pierrepont Finch in the Frank Loesser-Abe Burrows Pulitzer Prize-winning musical How To Succeed in Business Without Really Trying. The production swept the 1962 Tony Awards, including Morse’s win for Best Lead Actor in a Musical. His performance of the comic showstopper “I Believe In You,” with Finch serenading himself, was a show highlight.

Though Morse would return to Broadway four more times beginning in the early 1970s, he turned to film and television for much of the ’60s and subsequent decades, with roles in The Cardinal (1963), Honeymoon Hotel (1964), Quick, Before It Melts (1964), A Guide for the Married Man (1967), Oh Dad, Poor Dad, Mama’s Hung You in the Closet and I’m Feeling So Sad (1967) and, with Doris Day, Where Were You When the Lights Went Out? (1968).

A highlight of the era was his starring role in the funeral home satire The Loved One (1965), a dark comedy directed by Tony Richardson and written by Terry Southern and Christopher Isherwood, based on an Evelyn Waugh novel and Jessica Mitford’s savage 1963 expose of the funeral home business The American Way of Death.

Morse’s television career, meanwhile, remained both busy and steady. From the late 1950s and well into the 21st Century he appeared on such series as Alfred Hitchcock Presents, Car 54 Where Are You?, That’s Life, Love, American Style, Fantasy Island, One Day at a Time, The Dukes of Hazzard, Murder, She Wrote, Trapper John, Suddenly Susan, City of Angels and American Crime Story: The People v. O.J. Simpson, in which he played gadfly reporter Dominick Dunne.

A prolific voice actor, Morse had roles in The First Easter Rabbit, Jack Frost, Pound Puppies, Tiny Toon Adventures, Rugrats, Superman: The Animated Series, The Wild Thornberrys, and Teen Titans Go!, among others.

His television career would find its high-profile mark in 2007 with AMC’s Mad Men. As the recurring (and scene-stealing) Bertram Cooper, founding partner of the Sterling Cooper ad agency, Morse brought a comic flourish to the cutthroat Madison Avenue adventures. Often shoeless, occasionally dressed in a kimono, Morse’s Cooper was a wealthy, past-his-prime ad man with nothing left to prove. In one of the series’ most memorable exits, Cooper died peacefully after watching the 1969 moon landing and uttering a final, “Bravo.”

As for the Broadway stage, Morse would never abandon it. He was part of the original cast of 1972’s Sugar – the first musical adaptation of – and, in 1976, the short-lived musical So Long, 174th Street. His return to the Broadway stage 13 years later was nothing short of a triumph: He won his second Tony for his bravura performance as Capote and made Tru a hit.

Morse would be back on Broadway – at age 85 – in the starry 2016 revival of The Front Page, sharing the bill with, among others, Nathan Lane, John Goodman, Holland Taylor, Dylan Baker, Patricia Conolly and Morse’s old Mad Men co-star John Slattery.

Morse, whose first marriage (to actress Carole D’Andrea) ended in divorce, is survived by wife Elizabeth Roberts, daughters Andrea Doven, Hilary Morse, Robin Morse, all actresses; and two children by Roberts, son Charles Morse and daughter Allyn Morse.