[3] Fitzgerald started his acting career in 1980, at the age of eight, when he appeared as the youngest boy in Portland Player's production of Oliver!.

At age 26, in 1998, he starred in his first off-Broadway show, the controversial Corpus Christi by acclaimed playwright Terrence McNally.

[4] In 2002, Fitzgerald opened in the musical Amour, adapted from a 1943 French short story written by Marcel Aymé.

His performance earned him another nomination for the Drama Desk Award for Outstanding Featured Actor in a Musical.

For this performance, Fitzgerald won the Drama Desk Award for Outstanding Featured Actor in a Musical.

He starred as Pseudolus in an all-male production of Stephen Sondheim's A Funny Thing Happened on the Way to the Forum in his tenth season with the Williamstown Theatre Festival.

He played the role of Amos Hart in the Broadway production of Chicago, beginning October 28, 2013 and leaving on June 8, 2014.

[11] At the Williamstown Theatre Festival in July 2014 he played the role of Benny Fox in its production of June Moon.

[12] Christopher played the archangel Michael in the production of An Act of God starring Jim Parsons from May - August 2015 [1].

In March 2016, he joined the cast of Broadway transfer Waitress, playing the role of Ogie and stayed with the production on and off through 2021.

[15] Fitzgerald's first film role was a bit part in the movie Boiler Room starring Vin Diesel and Ben Affleck.

[16] Fitzgerald starred in 2012's Girl Most Likely alongside Kristen Wiig, Annette Bening, Matt Dillon and Darren Criss.