The Little Mermaid's Ursula and Queen Latifah - You can view it in the light that both crave that singing voice. Ursula steals if from Ariel and keeps it in that weird shell around her neck and Queen Latifah (a.k.a. Dana Elaine Owens) began as a musician and turned to acting. But in simpler terms, both are large and in this picture, their hair is the same color. Good enough.
The Sword in the Stone's Merlin and Richard Harris as Dumbledore in Harry Potter - Yeah, this may seem easy. But I very well could have chosen Ian McKellen or the new Dumbledore played by Michael Gambon instead of Richard Harris. But they don't really have the same look that Harris does. Maybe it has something to do with the eyebrows.
Peter Pan's Captain Hook and legendary Howard Stern - Okay, you have to use a little imagination for this one. It's not a perfect matchup. But it was either Howard or Weird Al and it came down to the hair. Also Captain Hook is tall (Howard's 6'5") and frequently complains (Howard often complains about his looks). Imagine Peter Pan being the FCC and cutting off Hook's hand which could metaphorically be Howard getting fired from NBC. But The King of All Media didn't peter out. Instead he came back and became a name synonymous with mischief.
Peter Pan and Justin Bieber - The boy who wouldn't grow up. Teenage girls flock to him. Some fly. But in the end, everyone despises him because every girl loves him (Wendy, Tiger Lily, Tinkerbell, etc). It's almost too similar. Maybe Bieber's shadow will run away from him.
The Lady and the Tramp's Peg and Goldie Hawn - There's no real similarities other than that they look alike. Not saying Goldie looks like a dog or whatever. Just the way Peg's bangs hang over her face and the way she struts around is quite reminiscent of a 1980's Goldie Hawn.
The Lion King's Rafiki and Morgan Freeman - Maybe it's because they both look so wise. Maybe it's because everyone loves them both. Maybe it's because of the white hair and beard. Or maybe it's because of the freckles.