In the following years he mainly focused on live performances and concerts. In 1999 Di Cataldo participated for the third and last time at the Sanremo Festival with the song "Come sei bella", which was followed by the album Dieci.
The same year he released his debut album, Siamo nati liberi, which was a commercial success replicated a year later by the album Anime (whose lead single, "Se adesso te ne vai", ranked fourth at the Big Artists competition of the Sanremo Music Festival) and in 1997 by the album Crescendo. Di Cataldo MassimoCrescendo
Sole
In fondo ad un bicchiere, nel buio di una stanza
in questo mio cantiere tra il sogno e la realt
io cerco di capire cerco di riassemblare i pezzi
di fare un p di luce nel vuoto che c' in me
ricordo da bambino che uscivo con mio padre.
In 1995 Di Cataldo entered the competition at the Sanremo Music Festival with the song "Che sarà di me", ranking second in the newcomers section.
The same year he was a finalist in the Castrocaro Music Festival. Born in Rome, after the high school Di Cataldo made several experiences poised between singing and acting, including a 1993 appearance in the Rai 2 TV-series I ragazzi del muretto in which he played a singer.
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