Off-Broadway and regional theatre Early in his career, Cuccioli spent several years learning the ropes off-Broadway at the Light Opera of Manhattan, starting out in the chorus, quickly moving up to smaller featured roles and then playing leading roles, such as Count Danilo in The Merry Widow, the Pirate King in The Pirates of Penzance, and Captain Corcoran in H.M.S. Pinafore. His other notable off-Broadway appearances include Nathan in the long-running revival of The Rothschilds (1990); the highly successful 1991 Kander and Ebb revue, And The World Goes 'Round, which garnered him an Outer Critics Circle Award in 1991; and he played the title role of in the Maury Yeston and Arthur Kopit musical, Phantom, at the Westchester Broadway Theater in 1992–93, a role that he has repeated. In 2000, he played Macheath in The Threepenny Opera. He was also seen as Karl Streber in Temporary Help in 2002 and in Mirette (a new musical by Harvey Schmidt) with York Theatre in 2005. Cuccioli's U.S. regional theatre credits include Ankles Aweigh at the Goodspeed Opera House in 1988, Jud Fry in Oklahoma! at the Paper Mill Playhouse in 1992, Archibald Craven in the Sacramento Music Circus production of The Secret Garden (1999), The Actor in Enter the Guardsman at the New Jersey Shakespeare Festival (1999 and again off-Broadway in 2000), King Marchan in Victor/Victoria at the Paper Mill in 2000, Nick Arnstein in Funny Girl (musical) at the Paper Mill in 2001, Antony in Antony and Cleopatra at the New Jersey Shakespeare Festival (2002), Captain von Trapp in The Sound of Music at the Paper Mill in 2003, and Sky Masterson in Guys and Dolls at the Paper Mill in 2004, with Karen Ziemba and Kate Baldwin. His 2005 theatrical credits include Alexander di Medici in Lorenzaccio at The Shakespeare Theatre in Washington, DC, and Capt. von Trapp in The Sound of Music at the Bendedum Theatre in Pennsylvania. He has also starred in shows at The Shakespeare Theatre of New Jersey, where he has played the title role in Macbeth (2004), Brutus in Julius Caesar (2005) and Antonio Salieri in Amadeus (2008), among others; at the New York's Equity Library Theatre; and in regional theatres around the United States. Cuccioli's later stage appearances include the off-Broadway revue, Jacques Brel is Alive and Well and Living in Paris in 2006. In June and July 2007, he played Claudius in Hamlet