During the 1930s he worked as an entertainer on board transatlantic liners on the routes between Europe and North America, which gave him the opportunity to get to know American music genres, especially jazz and swing.

Banned from the radio, Natalino Otto worked for recording companies instead, together with two great Italian bandleaders, Gorni Kramer and Pippo Barzizza.

[2] In the early 1960s, Otto retired from the public scene, but he continued to be involved in show organization, recordings and musical research.

His greatest hits were "Ho un sassolino nella scarpa", "Mamma voglio anch'io la fidanzata", "Mister Paganini", "Polvere di stelle", "Op op trotta cavallino", "Natalino studia canto", "Il valzer del boogie-woogie", "La classe degli asini".

Natalino Otto and his wife Flo Sandon's are credited with the discovery of one of Italy's greatest singers of all times – Mina.

On the night of 24 September 1958 the Happy Boys, a band of teen-age students was playing in the Rivaloro del Re dance hall, Cremona.