In 2001, James starred in Sweat the Small Stuff, a one-hour stand-up special for Comedy Central. In 2005 Kevin James and Ray Romano Executive Produced and starred in the HBO Sports Special Making the Cut: The Road to Pebble Beach. The documentary follows James and Romano as they attempt to make the cut at the annual Pebble Beach Pro-Am Golf Tournament. The special was nominated for a Sports Emmy.
James broke into the film world in 2005 in the Columbia Pictures box-office hit Hitch starring opposite Will Smith. In 2006, his voice was featured as the lead character, Otis, for the Nick Movies animated feature The Barnyard, and he provided voice work as well as movement for Officer Landers in the motion-capture animated film Monster House for Sony.
He starred opposite Adam Sandler in the 2007 hit comedy I Now Pronounce You Chuck and Larry.