The Choice Hotties Of 1999
Ryan Gosling, Jude Law, Joseph Gordon-Levitt, Matt Damon, Usher: a handful of these guys can still be classified as heartthrobs. Others, such as Carson Daly, Fred Durst, Sisqo, Brendan Fraser, and the like... perhaps not so much.
More findings from my time spent scanning my old teen mags.
Ryan Gosling

Teen Magazine
"Who's That Babe?" ...something that would never be uttered in 2012.
Joseph-Gordon Levitt

Teen Magazine
Jude Law

Teen Magazine
Justin Timberlake and Joey Fatone

Teen Magazine
Why does JT have two pairs of pants on, again?
Matt Damon

Teen Magazine
"Hottest Rising Star"
Jason Schwartzman

And the boys of Phantom Planet, Teen Magazine
"Cute band alert! Cute band alert!"
James Van Der Beek

Seventeen Magazine
Barry Watson

Us Weekly
Elijah Wood

Teen Magazine
Andrew Keegan and Rider Strong

Teen Magazine
Bonus appearances by the future Mrs. Timberlake, Jessica Biel, and Trina McGee-Davis, aka Angela on "Boy Meets World."
Joshua Jackson

Seventeen Magazine
Leonardo DiCaprio

People Magazine
Devon Sawa

Teen Magazine
Fred Durst

Teen Magazine
Also, Kid Rock? Really?
Jon Stewart

Us Weekly
Tobey Maguire

Teen Magazine
Hayden Christensen

Seventeen Magazine
"Your next crush"
Usher

Teen Magazine
Jonathan Jackson

Teen Magazine
Ethan Embry

Teen Magazine
Brendan Fraser

Us Weekly
Remember "George Of The Jungle" and George's romance with Leslie Mann?
Savage Garden

Jason Segel

Teen Magazine
I like that they had enough gumption to recognize Segel as a burgeoning star, but not enough resources to find any picture of him besides the "Freaks and Geeks" cast photo.
Jeremy Piven

Us Weekly
Remember "Cupid?"
David Lascher

Teen Magazine
"Who's that babe? Oh, just Ted from 'Hey Dude'..."
Carson Daly

Teen Magazine
(Okay, this one is from 2000 but included for the absurdity factor)