Beginning around 1916 at nineteen, he trained with Fernando Tanara for five years, then after a concert season, opera coach and voice teacher William S. Brady refined his voice over three more years. He sang baritone for the
Chicago Grand Opera. Robert Ringling appeared in the Grand Opera for the 1921 season in Florida. Robert E. Ringling appeared with the
San Carlo Opera Company in
Rigoletto and gave solo recitals across many cities before heading to Europe near the mid-1920s. His successful debut in
Ulm, Germany led to a
Munich engagement. By summer 1925, he returned from a successful run in Munich, holding a contract for the 1925 winter season and 1926 at the
Munich Opera. He committed to sing nineteen roles in the upcoming season, ten of them newly learned in German, with the contract ending August 31, 1926. His full-season agreement featured appearances in
Stuttgart,
Augsberg, and additional cities, with the Munich Opera appointing him leading baritone at its second-largest salary. The bank later liquidated in 1934, paying off all depositors in full. As an operatic baritone, he made his Chicago debut in 1929 as 'Tonio' in
Pagliacci. His rich baritone made him a favorite in Chicago, where he performed with
Samuel Insull's
Civic Opera Company for five seasons. ==Circus life==