Joel Gertner started out as a ring announcer in Extreme Championship Wrestling in 1995. Soon after, Shane Douglas influenced Gertner to become a heel and Gertner started taunting and making fun of the babyface wrestlers during their introduction to or in the ring and as a result, the face wrestlers usually made Gertner pay for his insults. He was then given the position of a color commentator by Taz and Bill Alfonso to counterbalance the influence of announcer Joey Styles, who they regarded as being biased against them. He also hosted a segment on ECW's weekly television program entitled Gertner Vision. During this time, Gertner became popular with the fans for his introductions, which would consist of limericks containing multiple sexual innuendos.
Gertner later became the manager and ring announcer for The Dudley Boyz, even going as far as to be called "Studley Dudley". At Barely Legal, the Dudleys faced The Eliminators for the ECW World Tag Team Championship. During the match, Gertner was hit by The Eliminators finishing move, the Total Elimination, and as a result he began wearing his infamous neckbrace. The Eliminators would go on to win the match and the titles as well. Joel involved himself in a six-man tag team match at 1998 Heat Wave, between Tommy Dreamer, The Sandman and Spike Dudley taking on D-Von, Big Dick and Bubba Ray, insulting head ECW referee John Finnigan. Later in the match, Joel was hung in the tree of woe and Finnigan baseball slid a steel chair into his face. Despite the 'injury', Joel led the Dudley Boyz to a record eight ECW Tag Team Title reigns.
Upon the Dudleys departure, Gertner then became a broadcaster on ECW on TNN alongside Joey Styles. Upon doing so, Gertner turned face and began feuding with The Network's representative Cyrus, and got unlikely support from broadcast partner (and former nemesis) Joey Styles. The feud came to a head at the 2000 edition of Anarchy Rulz in which Gertner faced Cyrus in a one on one match. Gertner won the match and ended the feud after assistance from The Sandman. Gertner remained with ECW until its closure on April 4, 2001. Gertner showed up on ECW's last pay-per-view Guilty as Charged, where he began to cut a promo before being attacked by Cyrus and Da Baldies. He returned later during the main event, attacking Cyrus and helping Rob Van Dam perform a Van Terminator on Jerry Lynn.
Gertner was a part of World Wrestling Entertainment's first-ever ECW One Night Stand reunion pay-per-view during which, in the course of two separate interviews with SmackDown! and Raw, he was pie-faced by John "Bradshaw" Layfield and begged on his hands and knees to then-Raw General Manager Eric Bischoff for a job.