Pressman was co-anchor (with Bill Ryan) of New York's first early-evening half-hour newscast, the "Pressman-Ryan Report," born out of a devastating 1963 New York City-area newspaper strike. He covered the New York region for NBC News, WNBC-TV and WNBC-AM radio. He was sent by the network to report on many historic events, including the 1956 sinking of the "Andrea Doria", Elvis Presley's Army stint which went through Brooklyn, one-on-one interviews with Marilyn Monroe, Harry S. Truman and Fidel Castro, the 1964 arrival of the Beatles at Kennedy Airport, the assassination of Malcolm X, chasing after newly inaugurated New York mayor John Lindsay in the streets during the 1966 transit strike, the 1968 Democratic National Convention in Chicago, where he reported on the clashes between demonstrators and police, and the aftermath of the assassinations of John F. Kennedy, Robert F. Kennedy and Martin Luther King Jr. Pressman was a reporter for NBC News at the Woodstock festival in upstate New York in 1969.