Tom Cruise on Tropic Thunder and Johnny Depp in Tusk are two of my favorites where a well known celebrity hid their identity pretty well with voices, prosthetics and makeup, to the point where I wouldn’t have guessed who they were.
In the Doctor Who series, “Time-Flight,” Anthony Ainley – who had played the Master several times at that point – was unrecognizable in the first episode and was billed as “Leon Ny Taiy” to hide the reveal.
Sarah Michelle Gellar in Doctor Horrible. She’s in the audience next to the 3 Captain Hammer fans during the shelter dedication. Wearing sunglasses. At night.
Dick Van Dyke as Mr Dawes Sr in Mary Poppins. The unscrambling anagram in the final credits suggests that his well disguised second role was intentionally a trick on the viewer.