He was promoted his second year at CGPS to dean of 7th and 8th grade students – an assistant principal position – and held that post, in addition to teaching music, until June 1991.

Lippa began his professional theatrical career at the Goodspeed Opera House in East Haddam, Connecticut.

The Goodspeed produced Lippa’s first musical, John & Jen (book by Tom Greenwald), in 1993 at the Norma Terris Theatre in Chester, Connecticut.

Following that period, producers Jeffrey Seller and Kevin McCollum optioned the play and, with the Manhattan Theater Club, made plans for production.

Texas State University's musical theatre department, under the direction of actress Kaitlin Hopkins, presented a revised version of the show in concert with Lippa conducting October 16–19.

[7] After producing Asphalt Beach, Stuart Oken asked Lippa to write the music and lyrics for The Addams Family (book by Marshall Brickman and Rick Elice).

The Addams Family starred Nathan Lane and Bebe Neuwirth, broke attendance records in Chicago during its 2009 try-out, and by its closing on December 31, 2011, had played 725 regular performances and 34 previews at the Lunt-Fontanne Theatre on Broadway.

For Halloween weekend, 2011, the Harrisburg Symphony Orchestra under the baton of Stuart Malina premiered The Addams Family Casket of Orchestral Grotesqueries, a symphonic suite from Lippa's musical The Addams Family, arranged by Lippa and Larry Hochman and orchestrated by Hochman.

A show called Jerry Christmas, with music and lyrics by Lippa and book by Daniel Goldfarb, was produced by New York Stage and Film in 2007 but has since been shelved.

The show, originally developed by Disney Theatrical and Tom Schumacher, had two readings in 2008 but didn't have its first full production until 2017, when it opened at the Bay Street Theater in Sag Harbor, New York.

Produced by James Yeoburn and Stuart Matthew Price of United Theatrical, the concert featured guest performances from Ashleigh Gray, Carrie Hope Fletcher, Jenna Russell, Tam Mutu, and Willemijn Verkaik.

[15] The Life of the Party: A Celebration of the Songs of Andrew Lippa premiered at London's Menier Chocolate Factory in May 2014.

Jazz phenom Peter Cincotti recorded Lippa's song “Raise The Roof” on his CD titled On The Moon (Phil Ramone, producer).

Vocal selections from The Addams Family, A Little Princess, The Wild Party and john & jen are published by Hal Leonard, and the shows are licensed by Music Theatre International.

Lippa married film marketing executive David Bloch in July 2008 in Los Angeles, California, shortly after that state's supreme court handed down a ruling permitting marriage of same-sex couples.