Known for the combative style he brought to his short

Known for the combative style he brought to his short-lived mid-1960s show, Les Crane was called the bad-boy of late- night television. He launched his software company two decades later, and it made him a multimillionaire.

Les Crane, called the "bad boy of late-night television" when he vied for ratings against talk-show king Johnny Carson in the mid-1960s, died of natural causes Sunday at Marin General Hospital in Greenbrae, north of San Francisco. He was 74. His death was announced by his daughter, Caprice Crane.

Crane was host of a popular radio call-in show in San Francisco when ABC tapped him in 1964 to star in "The Les Crane Show." Attempting to be both serious and witty, the program was touted as combining the approaches of Jack Paar, Mike Wallace and David Susskind, and featured conversations with major news figures, such as civil rights leader Malcolm X and Alabama Gov. George Wallace, as well as lighter chit-chat with movie stars and other celebrities.

Crane became known for his combative style and a long-nosed microphone that he aimed at his live audience like a shotgun. The show fizzled, but Crane had the last laugh. In 1984 he founded a software company that made him a multimillionaire, largely from the sales of the computer game "Chessmaster" and a widely used typing tutorial called "Mavis Beacon Teaches Typing." Crane helped develop both programs.

He also won a Grammy for his 1971 spoken-word recording of the poem Desiderata. With its New Age-y sentiments ("You are a child of the universe, no less than the trees and the stars. . . ."), it became a counterculture hit and a popular target for parody. The irreverent Crane later professed to prefer the parody.

Born in New York City on Dec. 3, 1933, Crane graduated from Tulane University in New Orleans, where he studied communications and psychology. He spent several years in the Air Force as a pilot and helicopter flight instructor before moving to San Francisco. There he hosted the radio talk show on KGO-AM that caught the attention of ABC television executives.

"The Les Crane Show" began a trial run in the summer of 1964, scoring some coups right away, including the first American television interview with the Rolling Stones. Other guests included singer Harry Belafonte on the civil rights struggle, Freudian analyst Theodore Reik on psychiatry, William F. Buckley on Republican politics and Wallace, the pro-segregation governor and candidate for president. "I wouldn't vote for you for dogcatcher," the handsome, sharp-tongued Crane told Wallace in his most-quoted interview.

"The Crane approach is entirely different from the Carson approach," UPI critic Rick Du Brow wrote in one of several kind reviews Crane received. "Whereas Carson offers generally neutralized chit-chat and plenty of variety-type entertainment, Crane hits hard at interviews, conversations and sequences from out on location. The big question is which approach has the greater lasting power -- whether the national digestive tract is able to down an occasional dish of meat and potatoes at midnight."

The answer, apparently, was no. Crane was fired and the show was renamed "ABC's Nightlife" and featured a roster of rotating hosts that included Shelley Berman, Dave Garroway and Pat Boone. When those changes did not bring the hoped-for ratings, ABC brought Crane back with Nipsey Russell as his sidekick, but the show fared little better than before and was canceled in late 1965.

"The material was so controversial in nature; we met issues head-on," Crane, explaining the show's demise, told Newsday in 1992. "Sponsors declined to be associated with that kind of show. Here would be Malcolm X getting a fair hearing, and this was in a country where there was an outcry because Harry Belafonte and Petula Clark held hands on TV."

In 1966, Crane married actress Tina Louise, best known as Ginger on the sitcom "Gilligan's Island." They were divorced after five years.

Married five times, he is survived by his wife of 20 years, Ginger Crane, of Belvedere, Calif; and Caprice, a television writer in Los Angeles who is his daughter with Louise.

After the show ended, Crane had another short-lived talk show and acted in a few television shows and movies, including the critically panned "An American Dream" (1966), based on the novel by Norman Mailer. He also tried medical school in Mexico but didn't like it and started a communications consulting firm instead.

Crane became interested in software after buying a personal computer to help him manage his consulting business. In 1984 he founded the company that became Software Toolworks. In time, the company not only developed software games but also duplicated and packaged software for other companies. In 1994 it was sold to the British company Pearson for $462 million. It is now owned by Learning Co., a leader in educational software.