Dugan is considered one of the industry's top feature film comedy directors, earning his reputation with such hits as Big Daddy and Happy Gilmore, both of which starred Adam Sandler; Saving Silverman, starring Jack Black, Steve Zahn and Amanda Peet; and Beverly Hills Ninja, starring Chris Farley. Most recently he directed The Benchwarmers, starring Rob Schneider, David Spade, Jon Heder and Jon Lovitz. He also directed National Security, starring Martin Lawrence.