Around 1908, he toured with Guy Brother's Minstrel Show, and helped form a vaudeville act "Weston, Fields and Carroll".

His first hit as a songwriter was "On the Mississippi" (1912), which he wrote the music for with Harry Carroll and Ballard MacDonald supplied the lyrics.

film Two Weeks With Love and thus got a renewed popularity which brought Fields large royalty incomes during his last two years.

For a period Fields also formed a vocal trio with brothers Jack and Irving Kaufman, billing themselves as "The Three Kaufields".

He suffered a stroke early in 1953 and was killed in a fire at Littlefield Nursing Home in Largo, Florida a little later the same year.