Kreischer grew up in Tampa, Florida. His mother worked in early childhood development and his father worked as a real-estate attorney. He attended a private Jesuit high school then went on to attend Florida State University (FSU). At FSU Kreischer majored in English and was a member of the Alpha Tau Omega fraternity. In 1997, during Kreischer's sixth year at FSU, the university was ranked number one by The Princeton Review in their annual list of the top "party schools" in the United States. Later that same year Kreischer became the focus of a 6-page article in Rolling Stone who named him "the top partier at the Number One Party School in the country." Titled "Bert Kreischer: The Undergraduate", the article recounted Kreicher's party hijinx, which included bouts of heavy drinking and public nudity. From the Rolling Stone article Director Oliver Stone optioned the rights to Kreischer's life. When the development deal with Oliver Stone fell through all the scripts that were submitted went back to their Writers. One of these Writers changed Kreischer's name and sold the script to National Lampoon. This became the basis for the 2002 film National Lampoon's Van Wilder starring Ryan Reynolds. When asked about his involvement in the film Kreischer told the New York Post in 2014: "I've never seen it. I had nothing to do with it." On Joe Rogan's podcast Kreischer talks about how he had National Lampoon executives confirmed that he was the basis for the Van Wilder movie and that National Lampoon did a radio show Partying with the original Van Wilder. He also confirmed that he would never sue National Lampoon for making the movie without his involvement.

Within five months of moving to New York City to pursue a career in comedy, Will Smith's Production Company offered Kreischer a deal for a sitcom. From 2001 to 2002 Kreischer served as host on the variety show The X Show. In 2001 he also made his acting debut starring in the CBS pilot Life With David J, starring alongside Elliott Gould and Peter Jacobson.

In 2004 Kreischer played a minor role on an episode of the police TV drama The Shield. That same year he starred on the FX series Hurt Bert that was based on a segment he had done for The X Show and featured him performing various dangerous Stunts.

In 2009 his first comedy special Bert Kreischer: Comfortably Dumb appeared on Comedy Central. His second special "Bert Kreischer: The Machine" was released in 2016 on Showtime.

In 2010, he became the host of the Travel Channel reality show Bert the Conqueror. The show featured Kreischer as he traveled to amusement parks and other entertainment venues across the United States in order to experience thrilling rides and activities. Kreischer, who suffers from a fear of heights, can be seen riding roller coasters and other amusement park rides as well as engaging in activities such as jumping off the Stratosphere tower in Las Vegas and being fired from a human slingshot.

Kreischer has served as host of the television series Hurt Bert on FX as well as Bert the Conqueror and Trip Flip on Travel Channel. He also appeared regularly as a guest on Rachael Ray from 2011 to 2015.

After 2 seasons, Bert the Conqueror went on hiatus and in 2012 Kreischer hosted the series Trip Flip also on Travel Channel. Trip Flip featured Kreischer surprising random people with the offer of an immediate 5-day vacation of his choosing. Trip Flip continued for 3 more seasons, ending in 2015. Bert the Conqueror returned for a third season in 2016.

In 2014 Kreischer's book Life of the Party: Stories of a Perpetual Man-Child was published by St. Martin's Press.

In 2015 he appeared on Comedy Central's comedy storytelling series This Is Not Happening. His story for the show was about his experience wrestling a bear for the television series Hurt Bert.