He is known for co-composing the musical Dead Outlaw[1] with David Yazbek, and for being the principal guitarist for pop singer Natalie Merchant.

[3] In 1994, Della Penna began touring with pop singer Joan Osborne on the Mercury Records label.

During this time he also toured with folk singer Joan Baez and joined the international band Hazmat Modine as a guitarist and songwriter.

[5] Della Penna also has his own band called Kill Henry Sugar,[6] a "metropolitan folk" duo with drummer Dean Sharenow.

It became a New York Times critic's pick[7] and earned eleven Drama Desk Award nominations, winning three.