Suggestions by @dannynguyen

James Bond

as Barry nelson in Which characters should actors have played in the '60s?

Lightning McQueen

as Elvis Presley in Which characters should actors have played in the '60s?

Dexter

as Jerry lewis in Which characters should actors have played in the '60s?

Mandark Astronomonov

as Daws butler in Which characters should actors have played in the '60s?

Diamonds (Rihanna song)

as Donald duck in AI Covers you want to hear

Never Gonna Give You Up

as Lincoln loud in AI Covers you want to hear

Cupid(song)

as Bubbles in AI Covers you want to hear

Ballin'

as Buttercup in AI Covers you want to hear

Daniel Craig

as James bond in Thunderball (2005)

Alfred Hitchcock

as Director in The Wolf Man (1961)

Jules Bass

as Producer in Rankin/Bass' Jimmy Neutron: Boy Genius (1971)

Arthur Rankin, Jr.

as Director in Rankin/Bass' Jimmy Neutron: Boy Genius (1971)