Chris Messina was 22 in You've Got Mail when he played the character 'Fox Salesperson'.
That was over 25 years ago in 1998.
This was his first recorded movie acting credit (although may not technically be his first actual acting role).
Today he is 48, and has starred in 52 movies in total, 47 of those since You've Got Mail was released.
In You've Got Mail, I think Chris Messina looks: