That was over 23 years ago in 1999.
Today he is 49, and has starred in 34 movies in total, 32 since Simon Sez was released.
In Simon Sez, I think Dane Cook looks:
Simon Sez scores 3.4 out of 10 on The Movie Database.
Dane Cook's first acting role was as 'Nick Miranda' in Simon Sez, released in 1999 when he was 26.