Boy Meets World
Shawn Hunter (Rider Strong) might just be one of our very favorite floppy haired boys. It was actually sad when the producers let him cut it in the 7th season and look more like the bad boy they had him play. Of course he wasn't really a bad boy. Does a bad boy have a geeky best friend and a strong girlfriend and write really sensitive poetry?
Joining Shawn with the floppy haired look was Eric Matthews (Will Friedle) who swung his shiny locks around with great zest and enthusiasm for plenty of years before they too fell to the axe of fashion changes. Eric's great strength was his hair and endless optimism and though they made him considerably more empty-headed in later seasons, his strength of heart and full of head of hair never let him down.
Felix King from Road to Avonlea
Mischievous ne'er do well Felix King (Zachary Bennett) was at the top of fashion in his day. Okay he was more in the 1900's then the 1990's but that was no excuse not to have him look his best for the viewing audience of the time. What little Canadian pre-teen didn't want to drag her fingers through those luscious locks?
Gus Pike
Along with Felix, Gus Pike (Michael Mahonen) is most definitely a floppy haired heartthrob of rural Canada. He didn't do the flop quite as vigorously as Felix, but he most definitely captured hearts with his accent, earnestness and fiddle-playing when we weren't focused on his hair, that is.
Friends
Chandler Bing (Matthew Perry) was the poster boy for 90's floppy hair, but only in the first season. After that, he seemed to show disdain for the fashion, despite the 7th season premiere, and a rather hideous edition that featured in a later season, he didn't go down that road again. But that's okay, because it's certainly his sarcasm and great husband bit that really draw us in.
Joey Tribbiani (Matt LeBlanc) also was a bit trendy in the first season and did a floppier style than he ever showed again. And we all know the ladies liked it, don't we?
Harvey from Sabrina the Teenage Witch
Harvey Kinkle (Nate Richert) was the epitome of floppy-haired stardom. We didn't love him for his brain or even his cute and gentle flirting with Sabrina, no, it was the hair and the confused look on his face.
Home Improvement
I doubt any picspam of the 90's would be complete without the Home Improvement boys. Brad (Zach Ty Bryan), Randy (Jonathan Taylor Thomas) and Mark (Taran Smith) practically grew up on our screens and all of them were floppy the whole way through. Without a doubt they represent the best of floppy-haired boys turning into hunks. We miss them, yes, we do. Good thing they have reruns.
Jesse from Full House
Now there have been mostly boys here, but undoubtedly Uncle Jesse (John Stamos) is a man. And he pulls off this look just like everything else he does. The man is a smoking sex symbol though we'd appreciate it if he never wore a mullet ever again. Uncle Jesse was what made this show half of what it was and undoubtedly his hair had a lot to do with it.
Jimmy from Lois and Clark: The New Adventures of Superman
Yes, we were all mad when they replaced Michael Landes as Jimmy Olsen. But...we have to say that Justin Whalin came in as his replacement and he nailed it. He was youthful, inquisitive, slightly dorky and floppy-haired to the extreme. All the ladies that came and went through the series seemed to like it as much as we did. We wish he'd had more screen time, if not for his personality, then at least for the hair.
Kevin from The Wonder Years
Kevin Arnold (Fred Savage) is a bit of a stretch here. He wasn't born with quite the head of curls that his brother Ben was, but he still couldn't be considered a full floppy-haired member. He did sport a bit of it when he could and he was such an iconic part of the 90's (and 60's) that we couldn't not include him.
Rich from Step by Step
Rich Halke (Jason Marsden) on the other hand, definitely qualifies for full membership to the floppy-haired boy club. His stint on Step by Step garnered all the best of that era. He was sweet, dim, a calming influence on Dana and his hair was always rocking to the latest floppy step.
Rob from Ghostwriter
Sadly Rob Baker (Todd Alexander) wasn't on Ghostwriter for very long, but he was most definitely one of the best bits about the show. He's shy, sensitive, a writer, but he dresses like a gangster and sports the best floppy do in Brooklyn and we loved him for it. Enjoy it, Australia.
Tommy from 3rd Rock From the Sun
Tommy Solomon (Joseph Gordon-Levitt) might have been mistaken for a little girl while in the earlier seasons, but as soon as he hit puberty, Tommy went through a major change and became a teenage heartthrob which is probably every elderly alien's dream, right? No matter what planet he's on, Tommy's hair is the very essence of awesome.
Zack from Saved by the Bell
Probably what we've all been waiting for, though he's by no means our favorite, Zack Morris (Mark-Paul Gosselaar) certainly was a huge part in sustaining this hair-style. His good looks and charm made him the most popular boy in high school and he definitely knew how to play it up. We adored watching him and his hair.
Raymond from Everybody Loves Raymond
We're giving an honorary mention to Ray Barone (Ray Ramono) who might not have the heartthrob status, but he certainly flopped a lot when he could get away with it.
By all means, this list is not conclusive and I certainly didn't even watch all these shows myself. The caps aren't that great. Some of the better of which were gathered from
thirdhex. Feel free to suggest other options and comment on your favorites and why.