Roland, a Pittsburgh, Pennsylvania native who graduated from California State University, Long Beach in 1964, began his broadcasting career in the 1960s. His first major assignment was for NBC News in Los Angeles in 1966. From there, he was hired as a reporter by KTTV, where he covered the Robert F. Kennedy assassination and the Charles Manson trial, and then went to sister station WNEW-TV (now WNYW) in New York City beginning in December, 1969. He remained with channel 5 for the remainder of his broadcasting career.
In his early years with WNEW/WNYW, he was a political reporter and weekend presenter for The 10 O'Clock News, and even did a cooking segment that was shown frequently on the newscast. He took over as the main presenter for the weeknight edition in 1979 after Bill Jorgensen, who had presented the newscast from its start in 1967, left to join the rival station WPIX. Over the years, Roland's co-presenters included Bill McCreary, Cora-Ann Mihalik and Rosanna Scotto. He left the 10:00 newscast in 2003 in order to prepare for his role as presenter of the new 5:00 and 6:00 PM newscasts that WNYW was preparing, which were launched that fall. His long run with the station came to an end on his retirement on June 4, 2004.
Roland is recently divorced from his wife of nine years, Joanna (married since 2003).
On May 11, 1983, Roland and his then-girlfriend were having a late-night dinner at the Racing Club, a restaurant on New York City's East Side. Three armed men entered the restaurant and attempted to rob customers. Roland disarmed one of the robbers and shot him in the leg. The other two robbers then attacked Roland. One of them struck him with a pistol, causing a laceration on his head that required 36 stitches. The police managed to arrest the three robbers and their getaway driver as they attempted to flee from the scene.
In January 1988, Roland was suspended by WNYW-TV (Fox) after an on-air argument with Joyce Patricia Brown, a mentally-ill homeless woman whom the Koch Administration sought to have confined to a mental hospital for treatment. Brown, who was represented by the New York City chapter of the American Civil Liberties Union, successfully challenged her incarceration in court. The interview quickly degenerated into an argument after Roland related his own personal experiences when encountering Brown on the street.
After the interview, numerous people called the station to protest Roland's treatment of Brown. The next day, the station suspended Roland, explaining that his emotions prevailed over his objectivity. Roland personally apologized to Brown, and the station broadcast a taped apology from him. After serving his brief suspension, Roland returned to the air.
On September 10, 2002, Roland was rushed to hospital after experiencing diverticulitis. Roland needed 18 blood transfusions, and doctors removed a part of his colon. Roland successfully recovered and returned to work at the station in late October.
Roland has appeared in several films, credited as a television anchor and himself once. Roland played television anchors in Hero at Large (1980), Eyewitness (1981) and The Object of My Affection (1998). He played himself in The Scout (1994). He played himself in three documentaries produced by filmmaker Dennis Michael Lynch, King of the Hamptons (2011) and 2012: They Come to America, The Cost of Illegal Immigration and 2013: They Come to America 2: The Cost of Amnesty.