Maybe not among the very best '90s movies, but still a strong contender for the most '90s movie. (The phones! The answering machines! The fashion! NHL '93 on Sega Genesis! The steering-wheel locks!)
If you Google "breakout performance," a photo of Vince Vaughn in this movie should rightfully be the first returned result.
Shoutout to Deena Martin, who only ended up with five credits on her IMDb page, but two of them are this and Dazed and Confused.