After college Dear directed and co-wrote the short film "Mr. Grey" (1969), which won an award at the Atlantic Film Festival. He then served as producer, director, and cinematographer on several low-budget exploitation features ("Nymph" 1975; "The Northville Cemetery Massacre" 1976) before meeting with writer-director Paul Schrader, then filming his directorial debut "Blue Collar" (1978). Dear was hired as a 2nd unit director and cameraman, and managed the 2nd unit on Schrader's subsequent "Hardcore" (1979).

Dear made his mainstream debut as a writer-director (in collaboration with executive producer and co-writer Nesmith) on "Timerider: The Adventure of Lyle Swan" (1983), an enjoyable fantasy starring Fred Ward as a time-traveling motorcyclist. He made a bigger splash with "Harry and the Hendersons", a Disney-styled comedy starring John Lithgow as a family man who takes in Bigfoot. A modest success in theaters, the film was a big hit on video and generated a syndicated TV spin-off. Dear tried his hand at teen comedy directing the James Bond spoof "If Looks Could Kill", and heroic adventure as the story writer of Disney's "The Rocketeer" (both 1991). He scored a modest hit helming "Angels in the Outfield" (1994), a sappy yet diverting Disney remake of a 1951 movie. At its best, the film recalled Disney sports fantasies from the 60s.