He is known for directing the films Problem Child, Brain Donors, Beverly Hills Ninja and National Security, and his partnership with comedic actor Adam Sandler, for whom he directed the films Happy Gilmore, Big Daddy, The Benchwarmers, I Now Pronounce You Chuck & Larry, You Don't Mess with the Zohan, Grown Ups, Just Go with It, Jack and Jill and Grown Ups 2.
Dugan made guest appearances on several TV series during the 1970s including The Mod Squad, The Waltons, Cannon, Columbo, The Rockford Files, and Alice.
[2] Dugan's other film credits of the 1980s include Water (1985), Can't Buy Me Love (1987), She's Having a Baby (1988), The New Adventures of Pippi Longstocking (1988) and Ron Howard's Parenthood (1989).
Dugan directed The Benchwarmers (2006), a comedy co-produced by Sandler, about a trio of men who try to make up for missed opportunities in childhood by forming a three-player baseball team to compete against Little League squads.
The film again stars Sandler, along with Kevin James, Chris Rock, David Spade, Rob Schneider, Salma Hayek, Maria Bello, and Maya Rudolph while Dugan had a bit part as a basketball referee; it was released in the summer of 2010 with major box office success.
Dugan wrote, directed and acted in Love, Weddings & Other Disasters in 2020, which starred Diane Keaton, Jeremy Irons, Maggie Grace and Andrew Bachelor.
A graduate of Notre Dame High School of Sherman Oaks, California, he played for five of the club's minor league teams through 2015, followed by shorter stays in the Chicago Cubs (2016) and Arizona Diamondbacks (2017) organizations before moving on to independent baseball (2018–2024).