Hutton was a contract player who was teamed early in his career with actress Paula Prentiss. They co-starred in four consecutive movies and were reportedly teamed because they were tallest actor (6'5") and actress (5'10") under contract to the studio.

Hutton made a name for himself in the 60s as a light romantic lead with deft comedic timing. Although he more than held his own against John Wayne in the dramas Hellfighters and The Green Berets, he was destined to play gangly, slightly goofball characters.