Prinze was first seen on television in attendance at the March 2008 WrestleMania XXIV pay-per-view and its preceding Hall of Fame ceremony. He also made a cameo on an episode of The Dirt Sheet, an online program hosted by wrestlers John Morrison and The Miz and had created an official profile on WWE's "Universe" blog community. His relationship with the company was furthered when he was hired as a member of the creative staff to contribute to weekly television and pay-per-view programming for the SmackDown brand. It was reported on February 22, 2009, that Prinze and WWE had parted ways.
On August 17, 2009, Prinze appeared on Raw as a special guest host, where he was assaulted by then-WWE Champion Randy Orton after refusing to bail Orton out of his tag team match with John Cena, who was due to challenge him in the upcoming SummerSlam. Prinze later returned to the program and got his payback during Orton's match with Cena against Big Show and Chris Jericho, by setting up a lumberjack match involving Mark Henry, Primo, Evan Bourne, Kofi Kingston, MVP and Jamie Noble.
Prinze returned to WWE on October 1, 2010, in a role as producer. On the November 1, 2010 episode of Monday Night Raw, Prinze made an on-screen appearance as Vince McMahon's doctor in a dream sequence scene that coincided with Linda McMahon's attempt to win a seat in the Senate for the state of Connecticut.