Damn, Josh Hartnett was the first that came to mind. Sherdog already all over it.
His co-star from American Pie is another name, but not on par with the other mentions we've already seen in this thread like Josh, and is easily the worst actor of the bunch: Chris Klein (Election, American Pie series, Here on Earth, Rollerball, We Were Soldiers, The United States of Leland).
If the question focused this on late 90's as the center, with the early 00's as the secondary, then it would be tough to beat frequent collaborators Matthew Lillard and Freddie Prinze Jr.
Ironically, Lillard starred with Jesse Bradford in the cult classic Hackers. Bradford's another mentionable for the 2000's crowd even if two of his best known works, Hackers and Romeo & Juliet, sort of break the temporal association by dipping all the way back to 1995 & 1996, respectively (Bring It On, Swimfan, Flags of our Fathers, Clockstoppers, recurring character on The West Wing).
BTW, goddamn, Dish Dogs has to be one of the most underrated IMDb scores I've ever seen. Only a 4.6 on IMDb? That's criminal.