In 1977, Osborne began his long-standing stint as a columnist for The Hollywood Reporter. The following year, he published 50 Golden Years of Oscar, which won the 1979 National Film Book award. Having joined the Los Angeles Film Critics Association, he was elected its President in 1981, and served as such till 1983. In 1982, Osborne began a five-year stint as the entertainment reporter on KTTV Channel 11 in Los Angeles. In addition, he began his Rambling Reporter column for The Hollywood Reporter, published five times weekly.