Starting out as a chorus and ensemble player, Berresse was afforded few actual occasions to act with his stage time, but did build up an impressive resume of credits beginning with 1990's Broadway revival of "Fiddler on the Roof". In 1992, he joined the Toronto production of Andrew Lloyd Webber's "Joseph and the Amazing Technicolor Dreamcoat", starring Donny Osmond, and was featured the following year in the revival of "Damn Yankees", staged at San Diego's Old Globe Theatre. When the production moved to Broadway's Marquis Theater, Berresse returned to the Great White Way and eventually assumed the leading role of Joe Hardy. 1995 saw him take on a role alongside Tommy Tune in the regional touring company of "Busker Alley" (also titled "Stage Door Charley" and "Buskers"), a musical set within a group of street performers in 1930s London. He was able to prove his range with the broader comedy "The Cocoanuts", written by Irving Berlin and made famous by the Marx Brothers. Manhattan's City Center Theater hosted a 1996 concert presentation of "One Touch of Venus" that featured Berresse's footwork, but that year's popular revival of "Chicago" would prove to be the catalyst for the performer's career boost.
Berresse took the role of doomed Fred Casely (murdered after jilting siren Roxie Hart six minutes into the show), and understudied the meatier part of slick defense attorney Billy Flynn, actually defending his own murder on nights that he stepped in for the role. In 1998, he assumed the co-starring role in a move that would establish the performer as a viable and versatile actor as well as talented song and dance man. He toured as Flynn in "Chicago" and in 1999 took a starring role in the short-lived Broadway revue "The Gershwins' Fascinating Rhythm". The curtain fell on that production soon after it raised, but Berresse bounced back shortly thereafter with a featured part in the celebrated 1999 Broadway revival of "Kiss Me, Kate". In this legendary play-within-a-play, he portrayed Bill Calhoun/Luciento, and drew on his gymnastic training to turn in a remarkable performance with a jaw-dropping number featuring some amazing acrobatics, dancing, leaping, flipping and virtually flying all around the three story set. Luckily for the production and for his further career, his work in "Kiss Me, Kate" didn't go unnoticed. In addition to glowing reviews and enviable buzz, Berresse was rewarded with a Tony nomination for Featured Actor in a Musical and was selected as one of three male nominees for the Astaire Award, a dance honor.