Gray's first in-studio show was Extreme Gong, an updated version of The Gong Show, on GSN in the late 1990s. He also hosted the first season of the American version of Junkyard Wars, which was nominated for a prime-time Emmy. Gray was chosen in 2001 by NBC Enterprises to host the daily syndicated American version of the game show The Weakest Link, which aired from 2002 to 2003. TV critic Steve Rogers likened Gray's hosting style to the demeanor of a "class clown", in contrast to the "severe schoolmarm" attitude of original Weakest Link host Anne Robinson. After hosting the reality series Todd TV on FX and the GSN special National Lampoon's Greek Games, in late 2004, Gray went on to become the co-host of NBC's $25 Million Dollar Hoax, and the host of ESPN's reality sports competition I'd Do Anything.