Following a tour of duty in the United States Army, Schlossberg attended college at New York University, graduating with honors.
In 1974, while working as an executive, Schlossberg began hosting Movie Talk, a four-hour nationally syndicated radio program aired in New York first on WMCA and subsequently on WOR.
Some of the features distributed by Castle Hill are three Elia Kazan features: Face in the Crowd, Baby Doll and America America; John Cassavetes' collection including Woman Under the Influence and Faces; Orson Welles' Othello, Woody Allen's What's Up Tiger Lily?, John Ford's Stagecoach, Alfred Hitchcock's Foreign Correspondent, Bruce Beresford's Breaker Morant, The Marx Brothers' A Night in Casablanca, Hell's Angels on Wheels and Rebel Rousers both starring Jack Nicholson, Glengarry Glen Ross starring Al Pacino, Death of a Salesman starring Dustin Hoffman, Seize the Day starring Robin Williams, presented with Martin Scorsese, Fellini's Intervista, two Academy Award nominees - A Great Day in Harlem and Al Hirschfeld: The Line King, and Academy Award winners Discreet Charm of the Bourgeoisie and Get Out Your Handkerchiefs.
Schlossberg established himself as a producer's representative for prominent figures such as Elia Kazan, Dustin Hoffman, John Cassavetes, and George C. Scott, Elaine May and Robert Duvall.
The company went on to record artists such as Peter, Paul & Mary, Joan Baez, Don McLean, The Washington Squares, and Judy Collins.
Guest speakers included Otto Preminger, David Susskind, Maximilian Schell, Elia Kazan and many others.