On December 6, 1993, Josh was given a call from his agent for an audition for All That. Josh stated that he went through a series of auditions to get on the show, which came to a total of 5-6 auditions for the directors/producers. And later, he became an Original Regular along with co-stars, "Angelique Bates, Lori Beth Denberg, Katrina Johnson, Kel Mitchell, Alisa Reyes, and Kenan Thompson".

Josh began on All That at age 14 from January 7 – March 30, 1994, along with his cast mates, Angelique Bates, Lori Beth Denberg, Alisa Reyes, Kel Mitchell, Kenan Thompson, Katrina Johnson. to tape the pilot for the show. His characters include Detective Dan, Earboy, Jimmy Bond Agent 1/7, and Bernie Kibbitz. In 1997, he and a few cast members starred in the 1997 feature film Good Burger (based on the All That sketch of the same name).

While he was on All That, Josh made guest appearances on other Nickelodeon shows. He appeared in a season 3 episode in The Secret World of Alex Mack in 1996. Starting in 1997, he and other All That alumni were panelists on the Nickelodeon Game Show, Figure It Out, later he stopped being a panelist in 1998. In 1999, he then appeared in the season 3 finale of Kenan & Kel, and the pilot for The Amanda Show, along with All That alumnus, Kenan Thompson.

After cast members Lori Beth, Kel, and Kenan had left All That in 1999, Josh and other Season 6 cast members of the show were not fully committed to filming All That, due to the fact that they were all getting older, and Josh seemed to be lost without his original co-stars from Seasons 1-5 (1994–1999), and leaving him to get through the brutal changes. After Server left, he was mainly famous for being the only cast member to remain through the entire original 6 seasons. After he and the last cast members of "The Golden Age" of All That had left, he moved on to host Oh Yeah! Cartoons for Season 3 in 2000-2001. Afterward, he made another guest appearance in a season 3 episode of 100 Deeds for Eddie McDowd in 2002.

Josh made a comeback in 2005, by returning to All That in the 10th Anniversary, and having a big role as reprising a few of his characters. In 2006, he made a guest appearance in a season 3 episode of Drake & Josh. In 2006, Josh began starring in the Web Series Laugh Out Loud with All That alumnus Kenan Thompson. In early 2007, he made his recent TV appearance in a season 3 episode of Ned's Declassified School Survival Guide.

Server was born in Highland Park, Illinois. He has a younger sister who was born in 1983. He is good friends with all of his cast mates on All That, including Kenan Thompson and Kel Mitchell. He's also good friends with TEENick series stars Drake Bell and Josh Peck, along with Miranda Cosgrove. Josh has stated in the 1998 collector's guide, "All That: Fresh out the Box", that his hobbies are going to the movies, rollerblading, the beach, and working out.

Server currently works and resides at Hollywood, California.