Alessandrini was born in
Boston, Massachusetts, grew up in
suburban
Needham, and graduated from
Xaverian Brothers High School in 1972. After graduating from the
Boston Conservatory of Music in 1977, he moved to
New York City. As a young actor, he appeared in summer stock, regional theater, and dinner theater productions of
Kismet,
The Fantasticks,
Oklahoma! and
Carousel, among others. He also worked at the off-Broadway
Light Opera of Manhattan. In late 1981, Alessandrini conceived and wrote a musical parody revue featuring spoofs of songs from Broadway musicals, on which he had been working while employed as a waiter at Lincoln Center. After a few months of weekend performances starring Alessandrini and a few friends at
Palsson's Supper Club, the show evolved into
Forbidden Broadway, which opened on January 15, 1982 at Palsson's Supper Club, with a cast featuring Alessandrini, Nora Mae Lyng, Bill Carmichael, Chloe Webb, and Fred Barton. The revue caught the theatergoing public's attention after
Rex Reed published a rave review and ultimately ran for 2,332 performances at Palsson's before moving on to other larger venues. It has subsequently been rewritten many times to include parodies of newer shows, and has had many different editions presented in New York City for more than 40 years. In 2006, the show and Alessandrini won
Tony Honors for Excellence in Theatre. The most recent incarnation,
Forbidden Broadway: Merrily We Stole a Song, played Off-Broadway in 2024. As a performer, Alessandrini can be heard on five of the 13
Forbidden Broadway cast albums, as well as the soundtracks of
Disney's animated films
Aladdin and
Pocahontas. He also co-wrote (with Pete Blue) and performed in the television parody
Masterpiece Tonight, a satirical salute to the 20th anniversary of
Masterpiece Theatre. In 1995, some of his sketches were featured in
Carol Burnett’s
CBS special,
Men, Movies and Carol. He has also written comedy specials for
Bob Hope and
Angela Lansbury for
NBC, as well as special material for Barbra Streisand's second duets album. Alessandrini's directorial credits include a production of Maury Yeston's
In The Beginning and a revue of Yeston's music and lyrics entitled
Anything Can Happen In The Theater. He also "politically updated" and directed a tongue-in-cheek adaptation of the 1962
Irving Berlin musical
Mr. President. In 2011, he co-created the musical comedy
The Nutcracker and I, with music by
Tchaikovsky, book by
Peter Brash and lyrics by Alessandrini. The musical debuted at the
George Street Playhouse in New Brunswick, New Jersey. In 2016, Alessandrini wrote and directed
Spamilton, which premiered at the
Triad Theater in New York and subsequently played in London, Los Angeles and Chicago. The show parodies
Hamilton and other Broadway musicals, and caricatures various Broadway stars. In recent years, Alessandrini has continued to update both
Forbidden Broadway and
Spamilton. His original musicals include
Madame X, written with Robert Hetzel, which was presented at part of the New York Musical Theatre Festival (NYMF) in 2011; and a musical version of
Moon Over Parador, written with Paul Mazursky and Bill Conti. ==Personal life==