27. Jason Lee
Why He Made The Cut: The original low-key cool guy.
There was not a nerdy white kid to be found in the mid '90s that did not want to be Jason Lee. He started as a professional skateboarder, appeared in a Sonic Youth video, and starred in multiple Kevin Smith movies. He was sharp, sarcastic and wore a mean corduroy blazerâ€”so, he had all the 90s cool guy essentials down.