James Shigeta, an actor who challenged social boundaries when he emerged in the late 1950s as one of the first Asian-Americans to play leading roles in Hollywood, died on Monday in Los Angeles. He was 85.

The cause was pulmonary failure, his brother Clarence said.

Shigeta traveled a distinctive path to stardom. He was born in the U.S. territory of Hawaii to a family of Japanese descent. His native language was English, but he first became an acting and singing star in Japan, where he took language lessons while performing in the 1950s. He served in the U.S. military during the Korean War.

His fame in Japan led to performances in Las Vegas, an appearance on "The Dinah Shore Show" and, in 1959, his first role in Hollywood, in "The Crimson Kimono." He starred as a detective who falls for a key witness in a case, played by Victoria Shaw.

"YES, this is a beautiful American girl in the arms of a handsome Japanese boy!" read a promotional poster for the film that showed the lovers kissing.

In 1960 he shared a Golden Globe for most promising newcomer. The next year he seemed to be fulfilling the prophecy, with leading roles in two films, "Bridge to the Sun," about an interracial couple, and "Flower Drum Song," an adaptation of the Rodgers and Hammerstein musical about arranged marriages — and resistance toward them — among some Japanese immigrants.

"What appealed to me about the two new pictures so much was the concepts," Shigeta told The New York Times in 1961. "They’re not the stereotyped idea of Orientals so many Westerners seem to have. In ‘Bridge,’ the man is a Japanese diplomat married to an American girl — a guy who’s articulate, has been educated in Europe and is a charming person. It’s the love of the couple, and their mutual humor, that actually eradicates the clich?s."

Shigeta did not ultimately break through to become a major star, but he went on to a long career as a character actor in movies and television, including roles on "Hawaii Five-O," "Medical Center," "Fantasy Island" and "The Love Boat." In 1988 he appeared in "Die Hard," playing an executive shot to death when he refuses to reveal a security code to the film’s villain, the terrorist Hans Gruber (Alan Rickman).

"Get on the jet to Tokyo to ask the chairman," Shigeta’s character says as Rickman reaches for a handgun. "I’m telling you, you’re just going to have to kill me."

James S. Shigeta was born on June 17, 1929, in Honolulu, although some sources incorrectly say he was born in 1933. He was one of six children of a plumber. In addition to his brother Clarence, his survivors include a sister, Barbara Sato; and two other brothers, Howard and Wilfred. He studied creative writing at New York University briefly before focusing on singing.

He emerged as a star in Japan after he appeared on Ted Mack’s "The Original Amateur Hour" talent show. Scouts for the show discovered Shigeta at an audition in Hawaii when he was 19, Clarence Shigeta said. JamesShigeta traveled to New York, where he won the show’s national competition and soon began singing in supper clubs in the United States, performing for a time under the name Guy Brion.

"It was my agent’s idea," he told The Associated Press in June 1960. "He thought I would get better acceptance as a Continental type."