 He wrote or co-wrote the Sandler films Billy Madison (1995), "Happy Gilmore" (1996), "The Wedding Singer" (1998), "The Waterboy" (1998), "Big Daddy" (1999) and "Pixels" (2015).In 1999, Herlihy appeared in the film "Big Daddy" as the "Singing Kangaroo," and sang "The Kangaroo Song" on the film's soundtrack.Herlihy played a bartender in both "The Wedding Singer" (1998) and "The Ridiculous 6" (2015).