George Clooney was 37 in South Park: Bigger, Longer & Uncut when he played the character 'Dr. Doctor (voice)'.
That was over 25 years ago in 1999.
Today he is 63, and has starred in 86 movies in total, 67 of those since South Park: Bigger, Longer & Uncut was released.
In South Park: Bigger, Longer & Uncut, I think George Clooney looks: