Suggestions by @rubynash

Edward Burns

as Josh Lucas in Clueless

Score: +1

Ben Barnes

as Josh Lucas in Clueless

Score: +1

Lily Collins

as Tai Frasier in Clueless

Score: 0

Lili Reinhart

as Tai Frasier in Clueless

Score: +1

Skai Jackson

as Dionne Davenport in Clueless

Score: +1

Abbey Lee

as Cherilyn Horowitz in Clueless

Score: +1

Alice Eve

as Cherilyn Horowitz in Clueless

Score: +1

Reese Witherspoon

as Cherilyn Horowitz in Clueless

Score: +2