Born in Springfield, Massachusetts, Weston had a keen interest in music from an early age and learned to play the piano. He was educated at Springfield High School, then attended Dartmouth College and Columbia University.
At Dartmouth he formed his own band and toured with the college band. He joined Columbia's dance band, The Blue Lions, but was temporarily unable to perform following a rail accident, and did some arrangements while he recovered. He sold his first arrangements to Joe Haymes in 1934. When Haymes requested more material, Weston's music was heard by Rudy Vallée, who offered him work on his radio show. Weston met Tommy Dorsey through Haymes and in 1936 became a member of Dorsey's orchestra. He persuaded Dorsey to hire The Pied Pipers after hearing them in 1938, and the group toured with the bandleader.
After leaving Dorsey in 1940, Weston worked with Dinah Shore and moved to Hollywood when he was offered film work. In California he met Johnny Mercer, who invited him to write for his new label, Capitol Records. Weston became music director there, where he worked with singer Jo Stafford and developed the mood music genre. Stafford moved with him to Columbia Records in 1950, and they were married in 1952.

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