Robert Morse, who starred in the famous American drama mad men, at the age of 90. His most famous role was as Bert Cooper, head of the show’s advertising agency, who gave his nickname to Sterling Cooper.

In a career spanning nearly 60 years, he has appeared in nearly 100 stage, television, and film productions, having first made his name in 1961 in a theatrical adaptation of How to Succeed in Business Without Really Trying, based on the bestselling Shepherd Mead book—which won She won a Tony Award for Best Actor in a Musical.

It was an achievement that would follow in 1990, winning Tony for Best Featured Actor in a Play, for his role as Truman Capote in True. Not only did it make him one of only four actors to win the highest acting Tonys for play and music, but it also earned him an Emmy three years later when the show was broadcast live on TV.

His role as the eccentric founder of the Mad Men advertising agency brought him international fame, earning him nominations for five Emmy Awards, and winning a Screen Actor’s Guild, as part of the ensemble cast. It saw him on his last episode paint on his Broadway skills for a slew of posthumous music, performing a singing and dancing routine to The Best Things in Life Are Free, after he died peacefully during Neil Armstrong’s 1969 moon landing.

“My good friend Bobby Morse has passed away at the age of 90,” Larry Karaszewski, writer/producer and vice president on the Board of Regents for the Academy of Motion Picture Arts and Sciences tweeted. “Huge talent and a beautiful soul. Sending love to son Charlie and daughter Aline. I’ve had so much fun with Bobby over the years – filming People v OJ and hosting several shows (How To Succeed, Loved One, That Life)”.