I’d say Marlon Brando, but it really was just aging, not caring, and weight gain. I mean, compared to Paul Newman or Robert Redford, Brando looked a lot different.
He was on TV a few years ago (IIRC, PBS) and I had no idea who that skinny 60-ish guy with the white crew cut and wire-framed glasses was until he started singing.
How about David Letterman and Michael Stipe, who currently look far more similar than most people could ever imagine? I think it’s the beards.
The parts between beard and hat are very clearly the same guy. If they look significantly different to you, it’s just the facial-hair version of the Clark Kent effect.
Melissa McCarthy’s weight loss has had a significant effect on her appearance. Watching the first season of Mike & Molly, I wouldn’t have recognized her based on seeing her in the later seasons, or Ghostbusters.