Based on the premise that father-child play is an important context for children's development and that fathers "specialize" in play, similarities and differences in the role of playfulness in the father-child and mother-child relationship were examined. Participants in this study included 111 families (children's age: 1-3 years). Father-child and mother-child play interactions were videotaped and coded for parental playfulness, sensitivity, structuring, and nonintrusiveness as well as child negativity. Results indicated that mothers and fathers did not differ in playfulness and that mothers and fathers who were higher in playfulness had children with lower levels of negativity. However, playfulness differently moderated the links between parents' and children's behaviors for mothers and fathers. A double-risk pattern was found for mothers, such that the links between child negativity and maternal sensitivity, structuring, and nonintrusiveness were significant only for the subgroup of mothers with low levels of playfulness. When mothers had high levels of playfulness, these effects were negligible. For fathers, a double-buffer pattern was revealed, indicating that the links between child negativity and paternal sensitivity and structuring were significant only for fathers with high levels of playfulness. When fathers had low levels of playfulness, these effects were negligible. These findings demonstrate the important role that parental playfulness has on parent-child interaction as well as the need to examine moderation patterns separately for fathers and mothers.