Arnold Stang, an actor who appeared alongside Milton Berle and Frank Sinatra and was known for his nerdy looks and distinctive nasal voice, has died. He was 91.

Arnold Stang died Sunday of pneumonia at Newton-Wellesley Hospital in Massachusetts, said JoAnne Stang, his wife of 60 years.

In films, he played Sparrow in The Man with the Golden Arm (1955) with Frank Sinatra and Kim Novak. In It’s a Mad, Mad, Mad, Mad World (1963) he played Ray, who along with his partner Irwin (played by Marvin Kaplan), owns a gas station that is destroyed by Jonathan Winters. He appeared in Hello Down There (1969). In one of the oddest movie pairings, he partnered with Arnold Schwarzenegger (billed as “Arnold Strong”) in the latter’s first film, the camp classic Hercules in New York (1970).