Alessandrini was born in Boston, Massachusetts, grew up in suburban Needham, and graduated from Xaverian Brothers High School in 1972.

He continued to appear in the revue, which caught the theatergoing public's attention after Rex Reed published a rave review[1] and ultimately ran for 2,332 performances in a number of venues.

Alessandrini can be heard on five of the eight Forbidden Broadway cast albums, as well as the soundtracks of Disney's animated films Aladdin and Pocahontas.

The musical debuted at the George Street Playhouse in New Brunswick, New Jersey during the 2011 Christmas season, directed by the theatre's artistic director, David Saint.

[3] In 2016, Alessandrini wrote the revue Spamilton, which premiered at the Triad Theater in New York and also plays at the Royal George Theatre in Chicago.